CA2406169C - Polyamide nucleic acid derivatives, and agents and processes for preparing them - Google Patents
Polyamide nucleic acid derivatives, and agents and processes for preparing them Download PDFInfo
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- CA2406169C CA2406169C CA2406169A CA2406169A CA2406169C CA 2406169 C CA2406169 C CA 2406169C CA 2406169 A CA2406169 A CA 2406169A CA 2406169 A CA2406169 A CA 2406169A CA 2406169 C CA2406169 C CA 2406169C
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- Prior art keywords
- pna
- pna derivative
- derivative
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- 102000039446 nucleic acids Human genes 0.000 title claims abstract description 26
- 108020004707 nucleic acids Proteins 0.000 title claims abstract description 26
- 150000007523 nucleic acids Chemical class 0.000 title claims abstract description 26
- 238000000034 method Methods 0.000 title claims description 38
- 239000003795 chemical substances by application Substances 0.000 title claims description 23
- 230000008569 process Effects 0.000 title claims description 11
- 239000004952 Polyamide Substances 0.000 title description 6
- 229920002647 polyamide Polymers 0.000 title description 6
- -1 phosphoryl groups Chemical group 0.000 claims abstract description 98
- 238000004132 cross linking Methods 0.000 claims abstract description 10
- 239000000032 diagnostic agent Substances 0.000 claims abstract description 8
- 229940039227 diagnostic agent Drugs 0.000 claims abstract description 8
- 230000003834 intracellular effect Effects 0.000 claims abstract description 7
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 3
- 238000004519 manufacturing process Methods 0.000 claims abstract 3
- 150000003254 radicals Chemical class 0.000 claims description 45
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 35
- 239000003153 chemical reaction reagent Substances 0.000 claims description 34
- YBJHBAHKTGYVGT-ZKWXMUAHSA-N (+)-Biotin Chemical compound N1C(=O)N[C@@H]2[C@H](CCCCC(=O)O)SC[C@@H]21 YBJHBAHKTGYVGT-ZKWXMUAHSA-N 0.000 claims description 27
- GNBHRKFJIUUOQI-UHFFFAOYSA-N fluorescein Chemical compound O1C(=O)C2=CC=CC=C2C21C1=CC=C(O)C=C1OC1=CC(O)=CC=C21 GNBHRKFJIUUOQI-UHFFFAOYSA-N 0.000 claims description 23
- 125000006239 protecting group Chemical group 0.000 claims description 21
- ZCCUUQDIBDJBTK-UHFFFAOYSA-N psoralen Chemical compound C1=C2OC(=O)C=CC2=CC2=C1OC=C2 ZCCUUQDIBDJBTK-UHFFFAOYSA-N 0.000 claims description 20
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 claims description 19
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 17
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- 239000011616 biotin Substances 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 14
- 238000002372 labelling Methods 0.000 claims description 14
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 13
- GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 claims description 12
- 230000000865 phosphorylative effect Effects 0.000 claims description 12
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol group Chemical group [C@@H]1(CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C)[C@H](C)CCCC(C)C HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 claims description 11
- VXGRJERITKFWPL-UHFFFAOYSA-N 4',5'-Dihydropsoralen Natural products C1=C2OC(=O)C=CC2=CC2=C1OCC2 VXGRJERITKFWPL-UHFFFAOYSA-N 0.000 claims description 10
- WCKQPPQRFNHPRJ-UHFFFAOYSA-N 4-[[4-(dimethylamino)phenyl]diazenyl]benzoic acid Chemical compound C1=CC(N(C)C)=CC=C1N=NC1=CC=C(C(O)=O)C=C1 WCKQPPQRFNHPRJ-UHFFFAOYSA-N 0.000 claims description 10
- 230000000692 anti-sense effect Effects 0.000 claims description 10
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 claims description 10
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 10
- QUHGSDZVAPFNLV-UHFFFAOYSA-N 4-[(5-acetamidofuran-2-carbonyl)amino]-n-[3-(dimethylamino)propyl]-1-propylpyrrole-2-carboxamide Chemical compound C1=C(C(=O)NCCCN(C)C)N(CCC)C=C1NC(=O)C1=CC=C(NC(C)=O)O1 QUHGSDZVAPFNLV-UHFFFAOYSA-N 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 9
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 9
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- MJYFVDNMTKLGTH-UHFFFAOYSA-N 4-bromo-6-(3,4-dichlorophenyl)sulfanyl-1-[[4-(dimethylcarbamoyl)phenyl]methyl]indole-2-carboxylic acid Chemical compound BrC1=C2C=C(N(C2=CC(=C1)SC1=CC(=C(C=C1)Cl)Cl)CC1=CC=C(C=C1)C(N(C)C)=O)C(=O)O MJYFVDNMTKLGTH-UHFFFAOYSA-N 0.000 claims description 8
- ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical group O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 claims description 8
- 230000001588 bifunctional effect Effects 0.000 claims description 8
- OPTASPLRGRRNAP-UHFFFAOYSA-N cytosine Chemical group NC=1C=CNC(=O)N=1 OPTASPLRGRRNAP-UHFFFAOYSA-N 0.000 claims description 8
- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- 239000011593 sulfur Substances 0.000 claims description 8
- ABZLKHKQJHEPAX-UHFFFAOYSA-N tetramethylrhodamine Chemical compound C=12C=CC(N(C)C)=CC2=[O+]C2=CC(N(C)C)=CC=C2C=1C1=CC=CC=C1C([O-])=O ABZLKHKQJHEPAX-UHFFFAOYSA-N 0.000 claims description 8
- 239000002773 nucleotide Substances 0.000 claims description 7
- 125000003729 nucleotide group Chemical group 0.000 claims description 7
- ANRHNWWPFJCPAZ-UHFFFAOYSA-M thionine Chemical compound [Cl-].C1=CC(N)=CC2=[S+]C3=CC(N)=CC=C3N=C21 ANRHNWWPFJCPAZ-UHFFFAOYSA-M 0.000 claims description 7
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 6
- 229930003427 Vitamin E Natural products 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 6
- 150000001450 anions Chemical class 0.000 claims description 6
- 229940104302 cytosine Drugs 0.000 claims description 6
- WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 claims description 6
- UYTPUPDQBNUYGX-UHFFFAOYSA-N guanine Chemical group O=C1NC(N)=NC2=C1N=CN2 UYTPUPDQBNUYGX-UHFFFAOYSA-N 0.000 claims description 6
- 239000000178 monomer Substances 0.000 claims description 6
- 239000007787 solid Substances 0.000 claims description 6
- RWQNBRDOKXIBIV-UHFFFAOYSA-N thymine Chemical group CC1=CNC(=O)NC1=O RWQNBRDOKXIBIV-UHFFFAOYSA-N 0.000 claims description 6
- 235000019165 vitamin E Nutrition 0.000 claims description 6
- 229940046009 vitamin E Drugs 0.000 claims description 6
- 239000011709 vitamin E Substances 0.000 claims description 6
- SHIBSTMRCDJXLN-UHFFFAOYSA-N Digoxigenin Natural products C1CC(C2C(C3(C)CCC(O)CC3CC2)CC2O)(O)C2(C)C1C1=CC(=O)OC1 SHIBSTMRCDJXLN-UHFFFAOYSA-N 0.000 claims description 5
- 229910019142 PO4 Inorganic materials 0.000 claims description 5
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 5
- 239000000654 additive Substances 0.000 claims description 5
- QONQRTHLHBTMGP-UHFFFAOYSA-N digitoxigenin Natural products CC12CCC(C3(CCC(O)CC3CC3)C)C3C11OC1CC2C1=CC(=O)OC1 QONQRTHLHBTMGP-UHFFFAOYSA-N 0.000 claims description 5
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 claims description 5
- 150000002431 hydrogen Chemical class 0.000 claims description 5
- 238000007901 in situ hybridization Methods 0.000 claims description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 5
- 239000010452 phosphate Substances 0.000 claims description 5
- 239000007790 solid phase Substances 0.000 claims description 5
- 125000006850 spacer group Chemical group 0.000 claims description 5
- 108091032973 (ribonucleotides)n+m Proteins 0.000 claims description 4
- OIVLITBTBDPEFK-UHFFFAOYSA-N 5,6-dihydrouracil Chemical compound O=C1CCNC(=O)N1 OIVLITBTBDPEFK-UHFFFAOYSA-N 0.000 claims description 4
- PEHVGBZKEYRQSX-UHFFFAOYSA-N 7-deaza-adenine Chemical compound NC1=NC=NC2=C1C=CN2 PEHVGBZKEYRQSX-UHFFFAOYSA-N 0.000 claims description 4
- KDCGOANMDULRCW-UHFFFAOYSA-N Purine Natural products N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 claims description 4
- 241000700605 Viruses Species 0.000 claims description 4
- 125000003275 alpha amino acid group Chemical group 0.000 claims description 4
- 230000008878 coupling Effects 0.000 claims description 4
- 238000010168 coupling process Methods 0.000 claims description 4
- 238000005859 coupling reaction Methods 0.000 claims description 4
- 238000001962 electrophoresis Methods 0.000 claims description 4
- 229940035893 uracil Drugs 0.000 claims description 4
- 125000001917 2,4-dinitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C(=C1*)[N+]([O-])=O)[N+]([O-])=O 0.000 claims description 3
- 206010028980 Neoplasm Diseases 0.000 claims description 3
- 229910052770 Uranium Inorganic materials 0.000 claims description 3
- 125000004442 acylamino group Chemical group 0.000 claims description 3
- 150000001413 amino acids Chemical class 0.000 claims description 3
- 235000012000 cholesterol Nutrition 0.000 claims description 3
- SHIBSTMRCDJXLN-KCZCNTNESA-N digoxigenin Chemical compound C1([C@@H]2[C@@]3([C@@](CC2)(O)[C@H]2[C@@H]([C@@]4(C)CC[C@H](O)C[C@H]4CC2)C[C@H]3O)C)=CC(=O)OC1 SHIBSTMRCDJXLN-KCZCNTNESA-N 0.000 claims description 3
- 108020004999 messenger RNA Proteins 0.000 claims description 3
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- 229940002612 prodrug Drugs 0.000 claims description 3
- 239000000651 prodrug Substances 0.000 claims description 3
- RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 claims description 3
- 229940113082 thymine Drugs 0.000 claims description 3
- 238000013518 transcription Methods 0.000 claims description 3
- 230000035897 transcription Effects 0.000 claims description 3
- 238000013519 translation Methods 0.000 claims description 3
- 125000006702 (C1-C18) alkyl group Chemical group 0.000 claims description 2
- TZMSYXZUNZXBOL-UHFFFAOYSA-N 10H-phenoxazine Chemical compound C1=CC=C2NC3=CC=CC=C3OC2=C1 TZMSYXZUNZXBOL-UHFFFAOYSA-N 0.000 claims description 2
- IZGFERLHOCMZQF-UHFFFAOYSA-N 2-(10h-phenoxazin-1-yloxy)ethanamine Chemical compound O1C2=CC=CC=C2NC2=C1C=CC=C2OCCN IZGFERLHOCMZQF-UHFFFAOYSA-N 0.000 claims description 2
- GIIGHSIIKVOWKZ-UHFFFAOYSA-N 2h-triazolo[4,5-d]pyrimidine Chemical compound N1=CN=CC2=NNN=C21 GIIGHSIIKVOWKZ-UHFFFAOYSA-N 0.000 claims description 2
- BISHACNKZIBDFM-UHFFFAOYSA-N 5-amino-1h-pyrimidine-2,4-dione Chemical compound NC1=CNC(=O)NC1=O BISHACNKZIBDFM-UHFFFAOYSA-N 0.000 claims description 2
- LQLQRFGHAALLLE-UHFFFAOYSA-N 5-bromouracil Chemical compound BrC1=CNC(=O)NC1=O LQLQRFGHAALLLE-UHFFFAOYSA-N 0.000 claims description 2
- ZFTBZKVVGZNMJR-UHFFFAOYSA-N 5-chlorouracil Chemical compound ClC1=CNC(=O)NC1=O ZFTBZKVVGZNMJR-UHFFFAOYSA-N 0.000 claims description 2
- JDBGXEHEIRGOBU-UHFFFAOYSA-N 5-hydroxymethyluracil Chemical compound OCC1=CNC(=O)NC1=O JDBGXEHEIRGOBU-UHFFFAOYSA-N 0.000 claims description 2
- LRSASMSXMSNRBT-UHFFFAOYSA-N 5-methylcytosine Chemical group CC1=CNC(=O)N=C1N LRSASMSXMSNRBT-UHFFFAOYSA-N 0.000 claims description 2
- QFVKLKDEXOWFSL-UHFFFAOYSA-N 6-amino-5-bromo-1h-pyrimidin-2-one Chemical compound NC=1NC(=O)N=CC=1Br QFVKLKDEXOWFSL-UHFFFAOYSA-N 0.000 claims description 2
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Classifications
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- C07H21/00—Compounds containing two or more mononucleotide units having separate phosphate or polyphosphate groups linked by saccharide radicals of nucleoside groups, e.g. nucleic acids
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
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- C07K14/001—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof by chemical synthesis
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- A61P31/16—Antivirals for RNA viruses for influenza or rhinoviruses
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T436/00—Chemistry: analytical and immunological testing
- Y10T436/14—Heterocyclic carbon compound [i.e., O, S, N, Se, Te, as only ring hetero atom]
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Landscapes
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- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
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- Biophysics (AREA)
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- Tropical Medicine & Parasitology (AREA)
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- Biotechnology (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
- Polyamides (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Investigating Or Analysing Biological Materials (AREA)
- Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10019135A DE10019135A1 (de) | 2000-04-18 | 2000-04-18 | Polyamidnukleinsäure-Derivate, Mittel und Verfahren zu ihrer Herstellung |
| DE10019135.5 | 2000-04-18 | ||
| PCT/EP2001/004030 WO2001079216A2 (de) | 2000-04-18 | 2001-04-07 | Polyamidnukleinsäure-derivate, mittel und verfahren zur ihrer herstellung |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2406169A1 CA2406169A1 (en) | 2001-10-25 |
| CA2406169C true CA2406169C (en) | 2012-06-19 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2406169A Expired - Fee Related CA2406169C (en) | 2000-04-18 | 2001-04-07 | Polyamide nucleic acid derivatives, and agents and processes for preparing them |
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| EP (1) | EP1276760B1 (enExample) |
| JP (1) | JP4908714B2 (enExample) |
| KR (1) | KR100842723B1 (enExample) |
| AR (1) | AR032153A1 (enExample) |
| AT (1) | ATE344276T1 (enExample) |
| AU (1) | AU5479501A (enExample) |
| BR (1) | BR0110110A (enExample) |
| CA (1) | CA2406169C (enExample) |
| CY (1) | CY1105958T1 (enExample) |
| DE (2) | DE10019135A1 (enExample) |
| DK (1) | DK1276760T3 (enExample) |
| ES (1) | ES2275677T3 (enExample) |
| IL (2) | IL152288A0 (enExample) |
| MX (1) | MXPA02009953A (enExample) |
| NO (1) | NO333193B1 (enExample) |
| NZ (1) | NZ521988A (enExample) |
| PT (1) | PT1276760E (enExample) |
| TW (1) | TWI298328B (enExample) |
| WO (1) | WO2001079216A2 (enExample) |
| ZA (1) | ZA200208344B (enExample) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20030165888A1 (en) * | 2001-07-18 | 2003-09-04 | Brown Bob D. | Oligonucleotide probes and primers comprising universal bases for diagnostic purposes |
| US6518017B1 (en) * | 1997-10-02 | 2003-02-11 | Oasis Biosciences Incorporated | Combinatorial antisense library |
| AU777910B2 (en) * | 1999-04-08 | 2004-11-04 | Gen-Probe Incorporated | Amplification and sequencing primer pairs and use thereof |
| DE10019135A1 (de) * | 2000-04-18 | 2001-10-31 | Aventis Pharma Gmbh | Polyamidnukleinsäure-Derivate, Mittel und Verfahren zu ihrer Herstellung |
| TWI286849B (en) * | 2003-03-25 | 2007-09-11 | Nichia Corp | Positive electrode active material for nonaqueous electrolyte secondary battery and nonaqueous electrolyte secondary battery |
| JP2010528615A (ja) * | 2007-05-31 | 2010-08-26 | サノフィ−アベンティス | ＮＡＰＥ−ＰＬＤ又はＡｂｈ４の活性を修飾する薬剤を同定するためのアッセイ方法 |
| US8703119B2 (en) * | 2007-10-05 | 2014-04-22 | Polygene Ltd. | Injectable biodegradable polymer compositions for soft tissue repair and augmentation |
| US20090276700A1 (en) * | 2008-04-30 | 2009-11-05 | Nokia Corporation | Method, apparatus, and computer program product for determining user status indicators |
| US20090276855A1 (en) * | 2008-04-30 | 2009-11-05 | Nokia Corporation | Method, apparatus, and computer program product that provide for presentation of event items |
| US20090276412A1 (en) * | 2008-04-30 | 2009-11-05 | Nokia Corporation | Method, apparatus, and computer program product for providing usage analysis |
| US20090276436A1 (en) * | 2008-04-30 | 2009-11-05 | Nokia Corporation | Method, apparatus, and computer program product for providing service invitations |
| US20090292762A1 (en) * | 2008-05-20 | 2009-11-26 | Nokia Corporation | Method, Apparatus, and Computer Program Product for Publishing Content |
| US20090327434A1 (en) * | 2008-06-30 | 2009-12-31 | Nokia Corporation | Method, Apparatus, and Computer Program Product for Anonymous Polling |
| USD696048S1 (en) * | 2010-08-12 | 2013-12-24 | Sealy Technology, Llc | Mattress |
| JP5990987B2 (ja) * | 2012-04-11 | 2016-09-14 | 株式会社Ihi | 微生物固定方法、および微生物検出方法 |
| JP2015172904A (ja) * | 2014-03-12 | 2015-10-01 | 株式会社東芝 | Ｌｄｏ型電圧レギュレータ、及び、受電装置 |
| US20180030065A1 (en) * | 2015-01-27 | 2018-02-01 | Isi Life Sciences, Inc. | Fluorescein polymer conjugates |
| KR102659194B1 (ko) * | 2016-07-26 | 2024-04-19 | 삼성전자주식회사 | 홀로그래픽 디스플레이 장치용 박형 백라이트 유닛 및 이를 포함하는 홀로그래픽 디스플레이 장치 |
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| EP0383803B1 (en) * | 1987-10-28 | 2000-05-03 | Howard Florey Institute Of Experimental Physiology And Medicine | Oligonucleotide-polyamide conjugates |
| DK51092D0 (da) | 1991-05-24 | 1992-04-15 | Ole Buchardt | Oligonucleotid-analoge betegnet pna, monomere synthoner og fremgangsmaade til fremstilling deraf samt anvendelser deraf |
| PL182237B1 (pl) * | 1994-03-07 | 2001-11-30 | Dow Chemical Co | Sposób przeprowadzania transfekcji komórek i osiagniecia biodostepnosci materialu genetycznego in vitro i ex vivo PL PL |
| DE4408528A1 (de) | 1994-03-14 | 1995-09-28 | Hoechst Ag | Peptid-Oligonucleotid-Derivate, deren Herstellung und Verwendung |
| DE4408531A1 (de) * | 1994-03-14 | 1995-09-28 | Hoechst Ag | PNA-Synthese unter Verwendung einer gegen schwache Säuren labilen Amino-Schutzgruppe |
| JP3307945B2 (ja) * | 1994-10-06 | 2002-07-29 | アイシス・ファーマシューティカルス・インコーポレーテッド | ペプチド核酸コンジュゲート |
| ES2165446T3 (es) * | 1995-03-13 | 2002-03-16 | Aventis Pharma Gmbh | Fosfonomonoester-acidos nucleicos, procedimiento para su preparacion y su utilizacion. |
| DE19508923A1 (de) * | 1995-03-13 | 1996-09-19 | Hoechst Ag | Phosphonomonoesternukleinsäuren, Verfahren zu ihrer Herstellung und ihre Verwendung |
| DE19640974A1 (de) * | 1996-10-04 | 1998-04-16 | Bayer Ag | Bausteine für DNA/PNA-Cooligomere |
| DE19757516A1 (de) * | 1997-12-23 | 1999-06-24 | Roche Diagnostics Gmbh | Modifizierte Nukleinsäureanaloga |
| US6326479B1 (en) * | 1998-01-27 | 2001-12-04 | Boston Probes, Inc. | Synthetic polymers and methods, kits or compositions for modulating the solubility of same |
| US6043352A (en) * | 1998-08-07 | 2000-03-28 | Isis Pharmaceuticals, Inc. | 2'-O-Dimethylaminoethyloxyethyl-modified oligonucleotides |
| DE10019135A1 (de) * | 2000-04-18 | 2001-10-31 | Aventis Pharma Gmbh | Polyamidnukleinsäure-Derivate, Mittel und Verfahren zu ihrer Herstellung |
| DE10019136A1 (de) * | 2000-04-18 | 2001-10-31 | Aventis Pharma Gmbh | Polyamidnukleinsäure-Derivate, Mittel und Verfahren zu ihrer Herstellung |
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2000
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2001
- 2001-04-07 MX MXPA02009953A patent/MXPA02009953A/es active IP Right Grant
- 2001-04-07 ES ES01927897T patent/ES2275677T3/es not_active Expired - Lifetime
- 2001-04-07 DE DE50111371T patent/DE50111371D1/de not_active Expired - Lifetime
- 2001-04-07 PT PT01927897T patent/PT1276760E/pt unknown
- 2001-04-07 IL IL15228801A patent/IL152288A0/xx unknown
- 2001-04-07 BR BR0110110-2A patent/BR0110110A/pt not_active IP Right Cessation
- 2001-04-07 AT AT01927897T patent/ATE344276T1/de active
- 2001-04-07 CA CA2406169A patent/CA2406169C/en not_active Expired - Fee Related
- 2001-04-07 JP JP2001576814A patent/JP4908714B2/ja not_active Expired - Fee Related
- 2001-04-07 EP EP01927897A patent/EP1276760B1/de not_active Expired - Lifetime
- 2001-04-07 WO PCT/EP2001/004030 patent/WO2001079216A2/de not_active Ceased
- 2001-04-07 AU AU5479501A patent/AU5479501A/xx not_active Withdrawn
- 2001-04-07 DK DK01927897T patent/DK1276760T3/da active
- 2001-04-07 KR KR1020027013932A patent/KR100842723B1/ko not_active Expired - Fee Related
- 2001-04-07 NZ NZ521988A patent/NZ521988A/xx not_active IP Right Cessation
- 2001-04-16 AR ARP010101766A patent/AR032153A1/es unknown
- 2001-04-17 US US09/835,371 patent/US6905820B2/en not_active Expired - Fee Related
- 2001-05-16 TW TW090108986A patent/TWI298328B/zh not_active IP Right Cessation
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2002
- 2002-10-14 IL IL152288A patent/IL152288A/en not_active IP Right Cessation
- 2002-10-15 NO NO20024959A patent/NO333193B1/no not_active IP Right Cessation
- 2002-10-16 ZA ZA200208344A patent/ZA200208344B/en unknown
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2004
- 2004-06-02 US US10/858,658 patent/US20050009073A1/en not_active Abandoned
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2007
- 2007-01-29 CY CY20071100108T patent/CY1105958T1/el unknown
- 2007-09-14 US US11/855,443 patent/US7550582B2/en not_active Expired - Fee Related
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2009
- 2009-05-29 US US12/474,532 patent/US7897346B2/en not_active Expired - Fee Related
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2011
- 2011-01-24 US US13/012,266 patent/US8268560B2/en not_active Expired - Fee Related
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| Date | Code | Title | Description |
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| MKLA | Lapsed |
Effective date: 20150407 |