JP2017518363A5 - - Google Patents
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- Publication number
- JP2017518363A5 JP2017518363A5 JP2017512102A JP2017512102A JP2017518363A5 JP 2017518363 A5 JP2017518363 A5 JP 2017518363A5 JP 2017512102 A JP2017512102 A JP 2017512102A JP 2017512102 A JP2017512102 A JP 2017512102A JP 2017518363 A5 JP2017518363 A5 JP 2017518363A5
- Authority
- JP
- Japan
- Prior art keywords
- group
- tert
- benzhydryloxycarbonyl
- atom
- guaninyl
- 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.)
- Granted
Links
- -1 nitrophenyl ester Chemical group 0.000 claims description 35
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 5
- 125000004185 ester group Chemical group 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 7
- HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 claims 5
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims 5
- 235000014304 histidine Nutrition 0.000 claims 5
- 229960002885 histidine Drugs 0.000 claims 5
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 claims 5
- 239000004475 Arginine Substances 0.000 claims 4
- AHLPHDHHMVZTML-BYPYZUCNSA-N L-Ornithine Chemical compound NCCC[C@H](N)C(O)=O AHLPHDHHMVZTML-BYPYZUCNSA-N 0.000 claims 4
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 claims 4
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 claims 4
- QIVBCDIJIAJPQS-VIFPVBQESA-N L-tryptophane Chemical compound C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-VIFPVBQESA-N 0.000 claims 4
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims 4
- 239000004472 Lysine Substances 0.000 claims 4
- AHLPHDHHMVZTML-UHFFFAOYSA-N Orn-delta-NH2 Natural products NCCCC(N)C(O)=O AHLPHDHHMVZTML-UHFFFAOYSA-N 0.000 claims 4
- UTJLXEIPEHZYQJ-UHFFFAOYSA-N Ornithine Natural products OC(=O)C(C)CCCN UTJLXEIPEHZYQJ-UHFFFAOYSA-N 0.000 claims 4
- QIVBCDIJIAJPQS-UHFFFAOYSA-N Tryptophan Natural products C1=CC=C2C(CC(N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-UHFFFAOYSA-N 0.000 claims 4
- 150000001413 amino acids Chemical group 0.000 claims 4
- 229960003121 arginine Drugs 0.000 claims 4
- 235000009697 arginine Nutrition 0.000 claims 4
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 claims 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 4
- 235000018977 lysine Nutrition 0.000 claims 4
- 229960003646 lysine Drugs 0.000 claims 4
- 229960003104 ornithine Drugs 0.000 claims 4
- 125000006239 protecting group Chemical group 0.000 claims 4
- MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 claims 3
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 3
- AYFVYJQAPQTCCC-GBXIJSLDSA-N L-threonine Chemical compound C[C@@H](O)[C@H](N)C(O)=O AYFVYJQAPQTCCC-GBXIJSLDSA-N 0.000 claims 3
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 claims 3
- MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 claims 3
- AYFVYJQAPQTCCC-UHFFFAOYSA-N Threonine Natural products CC(O)C(N)C(O)=O AYFVYJQAPQTCCC-UHFFFAOYSA-N 0.000 claims 3
- 239000004473 Threonine Substances 0.000 claims 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 125000001918 phosphonic acid ester group Chemical group 0.000 claims 3
- ABLZXFCXXLZCGV-UHFFFAOYSA-N phosphonic acid group Chemical group P(O)(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims 3
- 229960001153 serine Drugs 0.000 claims 3
- 229960002898 threonine Drugs 0.000 claims 3
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 claims 3
- 229960004441 tyrosine Drugs 0.000 claims 3
- 125000003088 (fluoren-9-ylmethoxy)carbonyl group Chemical group 0.000 claims 2
- DCXYFEDJOCDNAF-UHFFFAOYSA-N Asparagine Natural products OC(=O)C(N)CC(N)=O DCXYFEDJOCDNAF-UHFFFAOYSA-N 0.000 claims 2
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 claims 2
- XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 claims 2
- ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 claims 2
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 claims 2
- DCXYFEDJOCDNAF-REOHCLBHSA-N L-asparagine Chemical compound OC(=O)[C@@H](N)CC(N)=O DCXYFEDJOCDNAF-REOHCLBHSA-N 0.000 claims 2
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 claims 2
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 claims 2
- ZDXPYRJPNDTMRX-VKHMYHEASA-N L-glutamine Chemical compound OC(=O)[C@@H](N)CCC(N)=O ZDXPYRJPNDTMRX-VKHMYHEASA-N 0.000 claims 2
- AGPKZVBTJJNPAG-WHFBIAKZSA-N L-isoleucine Chemical compound CC[C@H](C)[C@H](N)C(O)=O AGPKZVBTJJNPAG-WHFBIAKZSA-N 0.000 claims 2
- ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 claims 2
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 claims 2
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 claims 2
- KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 claims 2
- ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Natural products CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 claims 2
- ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 claims 2
- KZSNJWFQEVHDMF-UHFFFAOYSA-N Valine Natural products CC(C)C(N)C(O)=O KZSNJWFQEVHDMF-UHFFFAOYSA-N 0.000 claims 2
- 229960003767 alanine Drugs 0.000 claims 2
- 235000004279 alanine Nutrition 0.000 claims 2
- 229960001230 asparagine Drugs 0.000 claims 2
- 235000009582 asparagine Nutrition 0.000 claims 2
- 229960005261 aspartic acid Drugs 0.000 claims 2
- 235000003704 aspartic acid Nutrition 0.000 claims 2
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 2
- 229960002433 cysteine Drugs 0.000 claims 2
- 235000018417 cysteine Nutrition 0.000 claims 2
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 claims 2
- 235000013922 glutamic acid Nutrition 0.000 claims 2
- 229960002989 glutamic acid Drugs 0.000 claims 2
- 239000004220 glutamic acid Substances 0.000 claims 2
- 235000004554 glutamine Nutrition 0.000 claims 2
- ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 claims 2
- 229960002743 glutamine Drugs 0.000 claims 2
- 235000014705 isoleucine Nutrition 0.000 claims 2
- 229960000310 isoleucine Drugs 0.000 claims 2
- AGPKZVBTJJNPAG-UHFFFAOYSA-N isoleucine Natural products CCC(C)C(N)C(O)=O AGPKZVBTJJNPAG-UHFFFAOYSA-N 0.000 claims 2
- 235000005772 leucine Nutrition 0.000 claims 2
- 229960003136 leucine Drugs 0.000 claims 2
- 235000006109 methionine Nutrition 0.000 claims 2
- 229930182817 methionine Natural products 0.000 claims 2
- 229960004452 methionine Drugs 0.000 claims 2
- 229960005190 phenylalanine Drugs 0.000 claims 2
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- 229960002429 proline Drugs 0.000 claims 2
- 229960004799 tryptophan Drugs 0.000 claims 2
- 239000004474 valine Substances 0.000 claims 2
- 229960004295 valine Drugs 0.000 claims 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 1
- GNVMUORYQLCPJZ-UHFFFAOYSA-M Thiocarbamate Chemical compound NC([S-])=O GNVMUORYQLCPJZ-UHFFFAOYSA-M 0.000 claims 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 1
- 125000005426 adeninyl group Chemical group N1=C(N=C2N=CNC2=C1N)* 0.000 claims 1
- GFFGJBXGBJISGV-UHFFFAOYSA-N adenyl group Chemical group N1=CN=C2N=CNC2=C1N GFFGJBXGBJISGV-UHFFFAOYSA-N 0.000 claims 1
- 239000002671 adjuvant Substances 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 230000009466 transformation Effects 0.000 claims 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 0 C*C(*)(*)CC(*)(*)N(*)C* Chemical compound C*C(*)(*)CC(*)(*)N(*)C* 0.000 description 4
- 108090000765 processed proteins & peptides Proteins 0.000 description 2
- MXKVWVBHAZNMRF-UHFFFAOYSA-N CNC(Cc(cc1)ccc1F)=O Chemical compound CNC(Cc(cc1)ccc1F)=O MXKVWVBHAZNMRF-UHFFFAOYSA-N 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 238000006664 bond formation reaction Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000006501 nitrophenyl group Chemical group 0.000 description 1
- 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102014007158.8A DE102014007158A1 (de) | 2014-05-16 | 2014-05-16 | Neue Peptid-Nukleinsäuren-Monomere und -Oligomere |
| DE102014007158.8 | 2014-05-16 | ||
| PCT/EP2015/000998 WO2015172889A1 (de) | 2014-05-16 | 2015-05-15 | Peptid-nukleinsäuren-monomere und -oligomere |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2017518363A JP2017518363A (ja) | 2017-07-06 |
| JP2017518363A5 true JP2017518363A5 (https=) | 2019-06-06 |
| JP6546272B2 JP6546272B2 (ja) | 2019-07-17 |
Family
ID=53267289
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017512102A Active JP6546272B2 (ja) | 2014-05-16 | 2015-05-15 | ペプチド核酸モノマー及びオリゴマー |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US20170166900A1 (https=) |
| EP (1) | EP3143038B8 (https=) |
| JP (1) | JP6546272B2 (https=) |
| KR (1) | KR102515760B1 (https=) |
| CN (1) | CN107074911B (https=) |
| AU (1) | AU2015258476B2 (https=) |
| CA (1) | CA2949185C (https=) |
| DE (1) | DE102014007158A1 (https=) |
| DK (1) | DK3143038T3 (https=) |
| ES (1) | ES2683186T3 (https=) |
| PL (1) | PL3143038T3 (https=) |
| RU (1) | RU2693827C2 (https=) |
| WO (1) | WO2015172889A1 (https=) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL266690B2 (en) * | 2016-11-16 | 2024-06-01 | Biomarin Tech Bv | Substances for targeting various selected organs or tissues |
| AU2018240467B2 (en) * | 2017-03-23 | 2022-09-15 | Neubase Therapeutics, Inc. | Peptide nucleic acid (PNA) monomers with an orthogonally protected ester moiety |
| WO2020124017A2 (en) * | 2018-12-13 | 2020-06-18 | Trucode Gene Repair, Inc. | Pna oligomers and related methods |
| EP3914261A4 (en) * | 2019-01-22 | 2023-06-28 | Korro Bio, Inc. | Rna-editing oligonucleotides and uses thereof |
| KR20210129646A (ko) | 2019-01-22 | 2021-10-28 | 코로 바이오, 인크. | Rna-편집 올리고뉴클레오타이드 및 그의 용도 |
| TW202043469A (zh) | 2019-01-22 | 2020-12-01 | 美商科羅生物公司 | Ｒｎａ編輯之寡核苷酸及其用途 |
| KR102403904B1 (ko) * | 2019-12-24 | 2022-06-02 | 주식회사 시선바이오머티리얼스 | 용액공정상 pna 올리고머의 제조방법 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5719262A (en) * | 1993-11-22 | 1998-02-17 | Buchardt, Deceased; Ole | Peptide nucleic acids having amino acid side chains |
| UA48150C2 (uk) * | 1994-11-02 | 2002-08-15 | Ай-Сі-Ен Фармасьютикалз | Похідні амінокислот або аміноспиртів, олігонуклеотид |
| JP3306073B2 (ja) * | 1996-07-24 | 2002-07-24 | ブヒャルト，ドルテ | 増加した結合親和性、配列特異性および溶解性を有するペプチド核酸 |
| IL133087A0 (en) * | 1997-05-28 | 2001-03-19 | Nielsen Peter E | Conjugated peptide nucleic acids having enhanced cellular uptake |
| DE19909373A1 (de) * | 1999-03-03 | 2000-10-05 | Ugichem | Neue PNA-Monomere, daraus resultierende PNA-Oligomere und deren Verwendung |
| DE102006034319A1 (de) * | 2006-07-21 | 2008-01-31 | Ugichem Gmbh | Chirale mit Phosponsäurester- oder Phosphonsäure- substituierte Verbindungen |
| DE102006050091A1 (de) * | 2006-10-24 | 2008-09-11 | Ugichem Gesellschaft für Organische Chemie mbH | Verfahren zur selektiven Lokalisierung von Wirkstoffen an und in Mitochondrien und entsprechende Wirkstoffe |
| US8575305B2 (en) * | 2008-06-04 | 2013-11-05 | Medical Research Council | Cell penetrating peptides |
-
2014
- 2014-05-16 DE DE102014007158.8A patent/DE102014007158A1/de not_active Withdrawn
-
2015
- 2015-05-15 CN CN201580038548.8A patent/CN107074911B/zh active Active
- 2015-05-15 US US15/311,704 patent/US20170166900A1/en active Pending
- 2015-05-15 DK DK15724512.7T patent/DK3143038T3/en active
- 2015-05-15 RU RU2016149427A patent/RU2693827C2/ru active
- 2015-05-15 AU AU2015258476A patent/AU2015258476B2/en active Active
- 2015-05-15 ES ES15724512.7T patent/ES2683186T3/es active Active
- 2015-05-15 PL PL15724512T patent/PL3143038T3/pl unknown
- 2015-05-15 KR KR1020167035152A patent/KR102515760B1/ko active Active
- 2015-05-15 WO PCT/EP2015/000998 patent/WO2015172889A1/de not_active Ceased
- 2015-05-15 JP JP2017512102A patent/JP6546272B2/ja active Active
- 2015-05-15 CA CA2949185A patent/CA2949185C/en active Active
- 2015-05-15 EP EP15724512.7A patent/EP3143038B8/de active Active
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