JP2013540102A5 - - Google Patents
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- JP2013540102A5 JP2013540102A5 JP2013516609A JP2013516609A JP2013540102A5 JP 2013540102 A5 JP2013540102 A5 JP 2013540102A5 JP 2013516609 A JP2013516609 A JP 2013516609A JP 2013516609 A JP2013516609 A JP 2013516609A JP 2013540102 A5 JP2013540102 A5 JP 2013540102A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- group
- methyl
- cycloalkyl
- alkenyl
- 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.)
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- 125000000217 alkyl group Chemical group 0.000 claims 144
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Natural products NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims 30
- 229940002612 prodrug Drugs 0.000 claims 28
- 239000000651 prodrug Substances 0.000 claims 28
- 229910052739 hydrogen Inorganic materials 0.000 claims 23
- 125000003118 aryl group Chemical group 0.000 claims 21
- 125000001072 heteroaryl group Chemical group 0.000 claims 18
- 239000004471 Glycine Substances 0.000 claims 16
- 125000003342 alkenyl group Chemical group 0.000 claims 14
- 125000004429 atom Chemical group 0.000 claims 13
- 229910052799 carbon Inorganic materials 0.000 claims 13
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 12
- 125000005842 heteroatom Chemical group 0.000 claims 12
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 12
- 229910052717 sulfur Inorganic materials 0.000 claims 12
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims 10
- 229910052760 oxygen Inorganic materials 0.000 claims 10
- 125000003277 amino group Chemical group 0.000 claims 9
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 claims 7
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims 7
- 239000004472 Lysine Substances 0.000 claims 7
- 235000004279 alanine Nutrition 0.000 claims 7
- 235000018417 cysteine Nutrition 0.000 claims 7
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 claims 7
- 235000018977 lysine Nutrition 0.000 claims 7
- 125000001963 4 membered heterocyclic group Chemical group 0.000 claims 6
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims 6
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims 6
- 239000004475 Arginine Substances 0.000 claims 6
- DCXYFEDJOCDNAF-UHFFFAOYSA-N Asparagine Natural products OC(=O)C(N)CC(N)=O DCXYFEDJOCDNAF-UHFFFAOYSA-N 0.000 claims 6
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 claims 6
- DCXYFEDJOCDNAF-REOHCLBHSA-N L-asparagine Chemical compound OC(=O)[C@@H](N)CC(N)=O DCXYFEDJOCDNAF-REOHCLBHSA-N 0.000 claims 6
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 claims 6
- AGPKZVBTJJNPAG-WHFBIAKZSA-N L-isoleucine Chemical compound CC[C@H](C)[C@H](N)C(O)=O AGPKZVBTJJNPAG-WHFBIAKZSA-N 0.000 claims 6
- ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 claims 6
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 claims 6
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 claims 6
- 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 6
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 claims 6
- KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 claims 6
- ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Natural products CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 claims 6
- MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 claims 6
- AYFVYJQAPQTCCC-UHFFFAOYSA-N Threonine Natural products CC(O)C(N)C(O)=O AYFVYJQAPQTCCC-UHFFFAOYSA-N 0.000 claims 6
- 239000004473 Threonine Substances 0.000 claims 6
- QIVBCDIJIAJPQS-UHFFFAOYSA-N Tryptophan Natural products C1=CC=C2C(CC(N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-UHFFFAOYSA-N 0.000 claims 6
- KZSNJWFQEVHDMF-UHFFFAOYSA-N Valine Natural products CC(C)C(N)C(O)=O KZSNJWFQEVHDMF-UHFFFAOYSA-N 0.000 claims 6
- 125000001931 aliphatic group Chemical group 0.000 claims 6
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 claims 6
- 235000009582 asparagine Nutrition 0.000 claims 6
- 229960001230 asparagine Drugs 0.000 claims 6
- 235000003704 aspartic acid Nutrition 0.000 claims 6
- 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 6
- 235000013922 glutamic acid Nutrition 0.000 claims 6
- 239000004220 glutamic acid Substances 0.000 claims 6
- ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 claims 6
- 125000005843 halogen group Chemical group 0.000 claims 6
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 claims 6
- AGPKZVBTJJNPAG-UHFFFAOYSA-N isoleucine Natural products CCC(C)C(N)C(O)=O AGPKZVBTJJNPAG-UHFFFAOYSA-N 0.000 claims 6
- 229960000310 isoleucine Drugs 0.000 claims 6
- 229930182817 methionine Natural products 0.000 claims 6
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 claims 6
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 claims 6
- 239000004474 valine Substances 0.000 claims 6
- 125000000623 heterocyclic group Chemical group 0.000 claims 5
- 229910052757 nitrogen Inorganic materials 0.000 claims 5
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims 4
- 125000002252 acyl group Chemical group 0.000 claims 3
- 150000001413 amino acids Chemical group 0.000 claims 3
- FUOOLUPWFVMBKG-UHFFFAOYSA-N 2-Aminoisobutyric acid Chemical compound CC(C)(N)C(O)=O FUOOLUPWFVMBKG-UHFFFAOYSA-N 0.000 claims 2
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims 2
- ONIBWKKTOPOVIA-SCSAIBSYSA-N D-Proline Chemical compound OC(=O)[C@H]1CCCN1 ONIBWKKTOPOVIA-SCSAIBSYSA-N 0.000 claims 2
- DTHNMHAUYICORS-KTKZVXAJSA-N Glucagon-like peptide 1 Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](C)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCCCN)C(=O)NCC(=O)N[C@@H](CCCNC(N)=N)C(N)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCCCN)NC(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CCC(N)=O)NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CO)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@@H](NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C)NC(=O)[C@@H](N)CC=1N=CNC=1)[C@@H](C)O)[C@@H](C)O)C(C)C)C1=CC=CC=C1 DTHNMHAUYICORS-KTKZVXAJSA-N 0.000 claims 2
- 239000002202 Polyethylene glycol Substances 0.000 claims 2
- 125000003630 glycyl group Chemical group [H]N([H])C([H])([H])C(*)=O 0.000 claims 2
- 229920001223 polyethylene glycol Polymers 0.000 claims 2
- 125000006850 spacer group Chemical group 0.000 claims 2
- 101710198884 GATA-type zinc finger protein 1 Proteins 0.000 claims 1
- 102000051325 Glucagon Human genes 0.000 claims 1
- 108060003199 Glucagon Proteins 0.000 claims 1
- XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 claims 1
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 claims 1
- KZNQNBZMBZJQJO-UHFFFAOYSA-N N-glycyl-L-proline Natural products NCC(=O)N1CCCC1C(O)=O KZNQNBZMBZJQJO-UHFFFAOYSA-N 0.000 claims 1
- 125000001429 N-terminal alpha-amino-acid group Chemical group 0.000 claims 1
- 102100040918 Pro-glucagon Human genes 0.000 claims 1
- MASNOZXLGMXCHN-ZLPAWPGGSA-N glucagon Chemical compound C([C@@H](C(=O)N[C@H](C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(O)=O)C(C)C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](C)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CO)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CO)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@@H](NC(=O)CNC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](N)CC=1NC=NC=1)[C@@H](C)O)[C@@H](C)O)C1=CC=CC=C1 MASNOZXLGMXCHN-ZLPAWPGGSA-N 0.000 claims 1
- 229960004666 glucagon Drugs 0.000 claims 1
- KZNQNBZMBZJQJO-YFKPBYRVSA-N glyclproline Chemical compound NCC(=O)N1CCC[C@H]1C(O)=O KZNQNBZMBZJQJO-YFKPBYRVSA-N 0.000 claims 1
- 108010077515 glycylproline Proteins 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 230000004962 physiological condition Effects 0.000 claims 1
- 108090000765 processed proteins & peptides Proteins 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US35818810P | 2010-06-24 | 2010-06-24 | |
| US61/358,188 | 2010-06-24 | ||
| PCT/US2011/040330 WO2011163012A2 (en) | 2010-06-24 | 2011-06-14 | Amide based glucagon superfamily peptide prodrugs |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2013540102A JP2013540102A (ja) | 2013-10-31 |
| JP2013540102A5 true JP2013540102A5 (enExample) | 2014-07-31 |
Family
ID=45372025
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013516609A Pending JP2013540102A (ja) | 2010-06-24 | 2011-06-14 | アミド結合を介して修飾されたグルカゴンスーパーファミリーのペプチドプロドラッグ |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US8778872B2 (enExample) |
| EP (1) | EP2588126A4 (enExample) |
| JP (1) | JP2013540102A (enExample) |
| KR (1) | KR20130102470A (enExample) |
| CN (1) | CN103179979A (enExample) |
| AR (1) | AR081471A1 (enExample) |
| CA (1) | CA2796894A1 (enExample) |
| MX (1) | MX2012014576A (enExample) |
| RU (1) | RU2580317C2 (enExample) |
| TW (1) | TW201209062A (enExample) |
| WO (1) | WO2011163012A2 (enExample) |
Families Citing this family (76)
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|---|---|---|---|---|
| CN101534846B (zh) | 2005-11-07 | 2014-11-05 | 印第安纳大学研究及科技有限公司 | 显示生理学溶解性和稳定性的胰高血糖素类似物 |
| US8454971B2 (en) | 2007-02-15 | 2013-06-04 | Indiana University Research And Technology Corporation | Glucagon/GLP-1 receptor co-agonists |
| ES2430067T3 (es) | 2007-03-28 | 2013-11-18 | President And Fellows Of Harvard College | Polipéptidos cosidos |
| EP2214691B1 (en) | 2007-10-30 | 2015-09-30 | Indiana University Research and Technology Corporation | Compounds exhibiting glucagon antagonist and glp-1 agonist activity |
| AU2008318986B2 (en) | 2007-10-30 | 2014-12-04 | Indiana University Research And Technology Corporation | Glucagon antagonists |
| WO2009099763A1 (en) | 2008-01-30 | 2009-08-13 | Indiana University Research And Technology Corporation | Ester-based peptide prodrugs |
| EP2676673B1 (en) | 2008-06-17 | 2016-11-16 | Indiana University Research and Technology Corporation | Glucagon/glp-1 receptor co-agonists |
| AR072159A1 (es) | 2008-06-17 | 2010-08-11 | Univ Indiana Res & Tech Corp | Analogos de glucagon, basados en (peptido insulinotropico dependiente de la glucosa) gip para el tratamiento de trastornos metabolicos y obesidad |
| JP5789515B2 (ja) | 2008-12-19 | 2015-10-07 | インディアナ ユニバーシティー リサーチ アンド テクノロジー コーポレーションＩｎｄｉａｎａ Ｕｎｉｖｅｒｓｉｔｙ Ｒｅｓｅａｒｃｈ Ａｎｄ Ｔｅｃｈｎｏｌｏｇｙ Ｃｏｒｐｏｒａｔｉｏｎ | インスリン類似体 |
| WO2010071807A1 (en) | 2008-12-19 | 2010-06-24 | Indiana University Research And Technology Corporation | Amide based glucagon superfamily peptide prodrugs |
| CA2744558A1 (en) | 2008-12-19 | 2010-07-15 | Indiana University Research And Technology Corporation | Amide-based insulin prodrugs |
| IN2012DN00377A (enExample) | 2009-06-16 | 2015-08-21 | Univ Indiana Res & Tech Corp | |
| IN2012DN06437A (enExample) * | 2010-01-27 | 2015-10-09 | Univ Indiana Res & Tech Corp | |
| WO2011143208A1 (en) | 2010-05-13 | 2011-11-17 | Indiana University Research And Technology Corporation | Glucagon superfamily peptides exhibiting g protein-coupled receptor activity |
| KR20130062931A (ko) | 2010-05-13 | 2013-06-13 | 인디애나 유니버시티 리서치 앤드 테크놀로지 코퍼레이션 | 핵 호르몬 수용체 활성을 나타내는 글루카곤 슈퍼패밀리 펩티드 |
| CN103068842B (zh) | 2010-06-16 | 2016-10-19 | 印第安纳大学研究及科技有限公司 | 对胰岛素受体具有高活性的单链胰岛素激动剂 |
| WO2011163462A2 (en) | 2010-06-24 | 2011-12-29 | Indiana University Research And Technology Corporation | Amide-based insulin prodrugs |
| PL2603600T3 (pl) | 2010-08-13 | 2019-06-28 | Aileron Therapeutics, Inc. | Makrocykle peptidomometyczne |
| PH12013501215A1 (en) | 2010-12-22 | 2013-11-18 | Univ Indiana Res & Tech Corp | Glucagon analogs exhibiting gip receptor activity |
| MX391293B (es) | 2011-06-10 | 2025-03-21 | Hanmi Science Co Ltd | DERIVADOs DE OXINTOMODULINA NOVEDOSOS Y COMPOSICION FARMACEUTICA PARA TRATAR LA OBESIDAD QUE COMPRENDE LOS MISMOS. |
| KR101577734B1 (ko) | 2011-06-17 | 2015-12-29 | 한미사이언스 주식회사 | 옥신토모듈린과 면역글로불린 단편을 포함하는 결합체 및 그의 용도 |
| SI2723367T1 (sl) | 2011-06-22 | 2017-08-31 | Indiana University Research And Technology Corporation | Koagonisti receptorja glukanona/GLP-1 |
| CN103748109A (zh) | 2011-06-22 | 2014-04-23 | 印第安纳大学研究及科技有限公司 | 胰高血糖素/glp-1受体共同激动剂 |
| CA2852468A1 (en) | 2011-10-18 | 2013-04-25 | Aileron Therapeutics, Inc. | Peptidomimetic macrocyles |
| RU2014117678A (ru) | 2011-11-17 | 2015-12-27 | Индиана Юниверсити Рисерч Энд Текнолоджи Корпорейшн | Пептиды глюкагонового суперсемейства, обладающие глюкокортикоидной рецепторной активностью |
| CN104114183A (zh) | 2011-12-20 | 2014-10-22 | 印第安纳大学研究及科技有限公司 | 用于治疗糖尿病的基于ctp的胰岛素类似物 |
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| WO2013133221A1 (ja) | 2012-03-04 | 2013-09-12 | 株式会社ボナック | microRNA阻害剤 |
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2011
- 2011-06-14 US US13/697,021 patent/US8778872B2/en active Active
- 2011-06-14 JP JP2013516609A patent/JP2013540102A/ja active Pending
- 2011-06-14 RU RU2013103093/04A patent/RU2580317C2/ru not_active IP Right Cessation
- 2011-06-14 CN CN201180031415XA patent/CN103179979A/zh active Pending
- 2011-06-14 MX MX2012014576A patent/MX2012014576A/es not_active Application Discontinuation
- 2011-06-14 WO PCT/US2011/040330 patent/WO2011163012A2/en not_active Ceased
- 2011-06-14 EP EP11798640.6A patent/EP2588126A4/en not_active Withdrawn
- 2011-06-14 KR KR1020127033177A patent/KR20130102470A/ko not_active Withdrawn
- 2011-06-14 CA CA2796894A patent/CA2796894A1/en not_active Abandoned
- 2011-06-23 TW TW100121933A patent/TW201209062A/zh unknown
- 2011-06-23 AR ARP110102184A patent/AR081471A1/es unknown
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