JP2006524182A5 - - Google Patents
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- JP2006524182A5 JP2006524182A5 JP2004554243A JP2004554243A JP2006524182A5 JP 2006524182 A5 JP2006524182 A5 JP 2006524182A5 JP 2004554243 A JP2004554243 A JP 2004554243A JP 2004554243 A JP2004554243 A JP 2004554243A JP 2006524182 A5 JP2006524182 A5 JP 2006524182A5
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- Japan
- Prior art keywords
- peptide
- group
- peptide according
- salt
- compound
- 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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- 108090000765 processed proteins & peptides Proteins 0.000 claims 37
- 125000003118 aryl group Chemical group 0.000 claims 11
- 229910052739 hydrogen Inorganic materials 0.000 claims 10
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims 8
- 150000003839 salts Chemical class 0.000 claims 8
- 125000000217 alkyl group Chemical group 0.000 claims 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 6
- 125000001424 substituent group Chemical group 0.000 claims 6
- 125000003342 alkenyl group Chemical group 0.000 claims 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims 5
- -1 thioalkyloxy Chemical group 0.000 claims 5
- YQAXFVHNHSPUPO-RNJOBUHISA-N 2-[[(2s)-2-[[2-[[(2s,4r)-1-[(2s)-1-(2-aminoacetyl)pyrrolidine-2-carbonyl]-4-hydroxypyrrolidine-2-carbonyl]amino]acetyl]amino]propanoyl]amino]acetic acid Chemical compound OC(=O)CNC(=O)[C@H](C)NC(=O)CNC(=O)[C@@H]1C[C@@H](O)CN1C(=O)[C@H]1N(C(=O)CN)CCC1 YQAXFVHNHSPUPO-RNJOBUHISA-N 0.000 claims 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 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
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- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 4
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- HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 claims 3
- AGPKZVBTJJNPAG-WHFBIAKZSA-N L-isoleucine Chemical compound CC[C@H](C)[C@H](N)C(O)=O AGPKZVBTJJNPAG-WHFBIAKZSA-N 0.000 claims 3
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- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 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
- 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 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
- ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Natural products CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 claims 3
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims 3
- 239000004472 Lysine Substances 0.000 claims 3
- ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-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
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- QIVBCDIJIAJPQS-UHFFFAOYSA-N Tryptophan Natural products C1=CC=C2C(CC(N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-UHFFFAOYSA-N 0.000 claims 3
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- 125000003545 alkoxy group Chemical group 0.000 claims 3
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- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 claims 3
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- 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 3
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- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 claims 3
- 229960002989 glutamic acid Drugs 0.000 claims 3
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- 239000004220 glutamic acid Substances 0.000 claims 3
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- 229930182817 methionine Natural products 0.000 claims 3
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- 229960005190 phenylalanine Drugs 0.000 claims 3
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 claims 3
- 229960002429 proline Drugs 0.000 claims 3
- 229960001153 serine Drugs 0.000 claims 3
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- 229960004799 tryptophan Drugs 0.000 claims 3
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- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 claims 3
- 125000001999 4-Methoxybenzoyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C(*)=O 0.000 claims 2
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical compound NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims 2
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- YNDUPGQMECPWKD-UHFFFAOYSA-N [O-][N+](=O)S[N+]([O-])=O Chemical compound [O-][N+](=O)S[N+]([O-])=O YNDUPGQMECPWKD-UHFFFAOYSA-N 0.000 claims 2
- 125000003368 amide group Chemical group 0.000 claims 2
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- WWTBZEKOSBFBEM-SPWPXUSOSA-N (2s)-2-[[2-benzyl-3-[hydroxy-[(1r)-2-phenyl-1-(phenylmethoxycarbonylamino)ethyl]phosphoryl]propanoyl]amino]-3-(1h-indol-3-yl)propanoic acid Chemical compound N([C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)O)C(=O)C(CP(O)(=O)[C@H](CC=1C=CC=CC=1)NC(=O)OCC=1C=CC=CC=1)CC1=CC=CC=C1 WWTBZEKOSBFBEM-SPWPXUSOSA-N 0.000 claims 1
- LFOIDLOIBZFWDO-UHFFFAOYSA-N 2-methoxy-6-[6-methoxy-4-[(3-phenylmethoxyphenyl)methoxy]-1-benzofuran-2-yl]imidazo[2,1-b][1,3,4]thiadiazole Chemical compound N1=C2SC(OC)=NN2C=C1C(OC1=CC(OC)=C2)=CC1=C2OCC(C=1)=CC=CC=1OCC1=CC=CC=C1 LFOIDLOIBZFWDO-UHFFFAOYSA-N 0.000 claims 1
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- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims 1
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- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims 1
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- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 1
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- KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 claims 1
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- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical class NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims 1
- OPFJDXRVMFKJJO-ZHHKINOHSA-N N-{[3-(2-benzamido-4-methyl-1,3-thiazol-5-yl)-pyrazol-5-yl]carbonyl}-G-dR-G-dD-dD-dD-NH2 Chemical compound S1C(C=2NN=C(C=2)C(=O)NCC(=O)N[C@H](CCCN=C(N)N)C(=O)NCC(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(N)=O)=C(C)N=C1NC(=O)C1=CC=CC=C1 OPFJDXRVMFKJJO-ZHHKINOHSA-N 0.000 claims 1
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- KGNDCEVUMONOKF-UGPLYTSKSA-N benzyl n-[(2r)-1-[(2s,4r)-2-[[(2s)-6-amino-1-(1,3-benzoxazol-2-yl)-1,1-dihydroxyhexan-2-yl]carbamoyl]-4-[(4-methylphenyl)methoxy]pyrrolidin-1-yl]-1-oxo-4-phenylbutan-2-yl]carbamate Chemical compound C1=CC(C)=CC=C1CO[C@H]1CN(C(=O)[C@@H](CCC=2C=CC=CC=2)NC(=O)OCC=2C=CC=CC=2)[C@H](C(=O)N[C@@H](CCCCN)C(O)(O)C=2OC3=CC=CC=C3N=2)C1 KGNDCEVUMONOKF-UGPLYTSKSA-N 0.000 claims 1
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
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Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US42897302P | 2002-11-25 | 2002-11-25 | |
| PCT/DK2003/000805 WO2004048400A1 (en) | 2002-11-25 | 2003-11-25 | Peptide gap junction modulators |
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| JP2006524182A JP2006524182A (ja) | 2006-10-26 |
| JP2006524182A5 true JP2006524182A5 (enExample) | 2007-01-18 |
| JP4603364B2 JP4603364B2 (ja) | 2010-12-22 |
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| JP2004554243A Expired - Fee Related JP4603364B2 (ja) | 2002-11-25 | 2003-11-25 | ペプチドギャップ結合モジュレーター |
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| EP (1) | EP1569953B1 (enExample) |
| JP (1) | JP4603364B2 (enExample) |
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| CN (1) | CN100558742C (enExample) |
| AT (1) | ATE482970T1 (enExample) |
| AU (1) | AU2003281986B2 (enExample) |
| BR (1) | BR0316488A (enExample) |
| CA (1) | CA2506490A1 (enExample) |
| DE (1) | DE60334396D1 (enExample) |
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| WO (1) | WO2004048400A1 (enExample) |
| ZA (1) | ZA200503600B (enExample) |
Families Citing this family (10)
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|---|---|---|---|---|
| US7153822B2 (en) | 2002-01-29 | 2006-12-26 | Wyeth | Compositions and methods for modulating connexin hemichannels |
| JP2008533114A (ja) * | 2005-03-18 | 2008-08-21 | ユーシーエル ビジネス パブリック リミテッド カンパニー | メカノ成長因子ペプチドおよびその使用 |
| GB0514071D0 (en) | 2005-07-07 | 2005-08-17 | Zealand Pharma As | N- or C- terminally modified small peptides |
| CN101336229B (zh) * | 2005-12-23 | 2012-06-13 | 西兰岛药物有限公司 | 改性的拟赖氨酸化合物 |
| JP2010533690A (ja) * | 2007-07-15 | 2010-10-28 | ジーランド・ファーマ・ア／エス | ペプチドギャップ結合モジュレーター |
| US8385414B2 (en) * | 2010-11-30 | 2013-02-26 | International Business Machines Corporation | Multimedia size reduction for database optimization |
| JP6441022B2 (ja) * | 2014-02-06 | 2018-12-19 | 国立大学法人大阪大学 | 骨粗鬆症予防又は治療用医薬 |
| WO2018202865A1 (en) | 2017-05-05 | 2018-11-08 | Zealand Pharma A/S | Gap junction intercellular communication modulators and their use for the treatment of diabetic eye disease |
| US12036286B2 (en) | 2021-03-18 | 2024-07-16 | Seagen Inc. | Selective drug release from internalized conjugates of biologically active compounds |
| GB202310195D0 (en) * | 2023-07-03 | 2023-08-16 | Hastings Nataly | Method for mitigating symptoms of neurological condition and a system therefor |
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| CA2321169C (en) * | 1998-01-23 | 2011-08-02 | Genencor International, Inc. | Modified enzymes and their use for peptide synthesis |
| EP1950224A3 (en) * | 1998-03-09 | 2008-12-17 | Zealand Pharma A/S | Pharmacologically active peptide conjugates having a reduced tendency towards enzymatic hydrolysis |
| EP1226160B1 (en) * | 2000-02-23 | 2004-12-15 | Zealand Pharma A/S | Novel antiarrhythmic peptides |
| MXPA03007537A (es) * | 2001-02-22 | 2005-09-30 | Zealand Pharma As | Usos medicos nuevos de compuestos que facilitan la comunicacion intercelular. |
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2003
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- 2003-11-25 ZA ZA200503600A patent/ZA200503600B/en unknown
- 2003-11-25 EP EP03773592A patent/EP1569953B1/en not_active Expired - Lifetime
- 2003-11-25 RU RU2005119978/04A patent/RU2005119978A/ru not_active Application Discontinuation
- 2003-11-25 WO PCT/DK2003/000805 patent/WO2004048400A1/en not_active Ceased
- 2003-11-25 CN CNB2003801040913A patent/CN100558742C/zh not_active Expired - Fee Related
- 2003-11-25 ES ES03773592T patent/ES2353666T3/es not_active Expired - Lifetime
- 2003-11-25 CA CA002506490A patent/CA2506490A1/en not_active Abandoned
- 2003-11-25 NZ NZ540155A patent/NZ540155A/en unknown
- 2003-11-25 DK DK03773592.5T patent/DK1569953T3/da active
- 2003-11-25 MX MXPA05005444A patent/MXPA05005444A/es active IP Right Grant
- 2003-11-25 JP JP2004554243A patent/JP4603364B2/ja not_active Expired - Fee Related
- 2003-11-25 US US10/534,201 patent/US20060194947A1/en not_active Abandoned
- 2003-11-25 AT AT03773592T patent/ATE482970T1/de not_active IP Right Cessation
- 2003-11-25 BR BR0316488-8A patent/BR0316488A/pt not_active Application Discontinuation
- 2003-11-25 DE DE60334396T patent/DE60334396D1/de not_active Expired - Lifetime
- 2003-11-25 KR KR1020057009468A patent/KR20050086846A/ko not_active Withdrawn
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2005
- 2005-06-21 NO NO20053053A patent/NO20053053L/no not_active Application Discontinuation
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