RU94011276A - CYCLOPEPTIDES, METHOD OF THEIR PRODUCTION, CONTAINING THEIR PHARMACEUTICAL COMPOSITIONS AND METHOD OF THEIR PRODUCTION - Google Patents
CYCLOPEPTIDES, METHOD OF THEIR PRODUCTION, CONTAINING THEIR PHARMACEUTICAL COMPOSITIONS AND METHOD OF THEIR PRODUCTIONInfo
- Publication number
- RU94011276A RU94011276A RU94011276/04A RU94011276A RU94011276A RU 94011276 A RU94011276 A RU 94011276A RU 94011276/04 A RU94011276/04 A RU 94011276/04A RU 94011276 A RU94011276 A RU 94011276A RU 94011276 A RU94011276 A RU 94011276A
- Authority
- RU
- Russia
- Prior art keywords
- asp
- arg
- formula
- gly
- phe
- Prior art date
Links
- 102000001189 Cyclic Peptides Human genes 0.000 title claims 3
- 108010069514 Cyclic Peptides Proteins 0.000 title claims 3
- 239000008194 pharmaceutical composition Substances 0.000 title claims 3
- 150000001875 compounds Chemical class 0.000 claims 6
- 150000003839 salts Chemical class 0.000 claims 6
- 239000011780 sodium chloride Substances 0.000 claims 6
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 claims 3
- 125000004432 carbon atoms Chemical group C* 0.000 claims 3
- 125000000998 L-alanino group Chemical group [H]N([*])[C@](C([H])([H])[H])([H])C(=O)O[H] 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 125000000267 glycino group Chemical group [H]N([*])C([H])([H])C(=O)O[H] 0.000 claims 2
- 239000007788 liquid Substances 0.000 claims 2
- -1 -HN-Q-CO- Chemical group 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
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 claims 1
- ZDXPYRJPNDTMRX-VKHMYHEASA-N L-glutamine Chemical compound OC(=O)[C@@H](N)CCC(N)=O ZDXPYRJPNDTMRX-VKHMYHEASA-N 0.000 claims 1
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 claims 1
- 125000000510 L-tryptophano group Chemical group [H]C1=C([H])C([H])=C2N([H])C([H])=C(C([H])([H])[C@@]([H])(C(O[H])=O)N([H])[*])C2=C1[H] 0.000 claims 1
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 150000007513 acids Chemical class 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 150000003862 amino acid derivatives Chemical class 0.000 claims 1
- 125000000539 amino acid group Chemical group 0.000 claims 1
- 150000001413 amino acids Chemical class 0.000 claims 1
- 150000007514 bases Chemical class 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- 125000001589 carboacyl group Chemical group 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- 239000002552 dosage form Substances 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims 1
- 238000007327 hydrogenolysis reaction Methods 0.000 claims 1
- 239000003112 inhibitor Substances 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims 1
- 229910052740 iodine Inorganic materials 0.000 claims 1
- 239000011630 iodine Substances 0.000 claims 1
- 239000007787 solid Substances 0.000 claims 1
- 238000003797 solvolysis reaction Methods 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
Claims (8)
Цикло-/ Arg-B-Asp-D-E/,
где В обозначает Gly, Ala, -HN-Q-CO;
D и E, каждый независимо друг от друга, обозначают: Gly, -HN-Q-CO-, Ala, Asn, Asp, Аsp(OR), Arg, Cha, Cys, Gln, Glu, His, Ile, Leu, Lуs, Lys(Ac), Lys(AcNH2), Lys(AcSH), Met, Nal, Nle, Orn, Phe, 4-Hal-Phe, Phg, Pro, Pya, Ser, Thr, Tia, Tic, Trp, Tyr oder Val
причем указанные аминокислотные остатки также могут быть дериветизированы;
R обозначает алкил с 1-6 С-атомами;
Hal обозначает фтор, хлор, бром, йод;
Q обозначает алкилен с 1 - 6 С-атомами ;
Ас обозначает алканоил с 1 - 10 С-атомами,
причем, поскольку речь идет об остатках оптически активных аминокислот и производных аминокислот, то включаются также и L-формы,
а также их физиологически приемлемые соли.1. Cyclopeptides of formula (I):
Cyclo- / Arg-B-Asp-DE /,
where B stands for Gly, Ala, -HN-Q-CO;
D and E, each independently of the others, denote: Gly, -HN-Q-CO-, Ala, Asn, Asp, As (OR), Arg, Cha, Cys, Gln, Glu, His, Ile, Leu, Ls , Lys (Ac), Lys (AcNH 2 ), Lys (AcSH), Met, Nal, Nle, Orn, Phe, 4-Hal-Phe, Phg, Pro, Pya, Ser, Thr, Tia, Tic, Trp, Tyr oder val
moreover, said amino acid residues can also be derivatized;
R is alkyl with 1-6 C-atoms;
Hal means fluorine, chlorine, bromine, iodine;
Q denotes alkylene with 1 to 6 carbon atoms;
Ac denotes alkanoyl with 1-10 C-atoms,
moreover, since we are talking about residues of optically active amino acids and amino acid derivatives, L-forms are also included,
and their physiologically acceptable salts.
(a) Cyclo-(Arg-Gly- Asp-D-Lys-Val);
(b) cyclo-(Arg-Gly- Asp-D-Phe-Lys);
(c) Cyclo-(Arg-Gly-Asp- D-Phe-Gly);
(d) Cyclo-(Arg-Gly- Asp-D-Phe-Phe);
(e) Cyclo-(Arg-Gly- Asp-D-Phe-Leu);
(f) Cyclo-(Arg-Gly-Asp- Phe-D-Leu).3. Cyclopeptides of the formula II according to claim 1, representing
(a) Cyclo- (Arg-Gly-Asp-D-Lys-Val);
(b) cyclo- (Arg-Gly-Asp-D-Phe-Lys);
(c) Cyclo- (Arg-Gly-Asp-D-Phe-Gly);
(d) Cyclo- (Arg-Gly-Asp-D-Phe-Phe);
(e) Cyclo- (Arg-Gly-Asp-D-Phe-Leu);
(f) Cyclo- (Arg-Gly-Asp-Phe-D-Leu).
или пептид формулы (II): Н-Z-ОН,
где Z обозначает -ARg-B-Asp-D-E; -B-Asp-D-E-Arg; -Asp-D-E-Arg-B-D-E-Arg-B-Asp- или E-Arg-B-Asp-D-,
или реакционноспособное производное такого пептида обрабатывают циклизующим средством;
и/или основное или кислое соединение формулы (I) путем обработки с помощью кислоты или основания переводят в одну из его солей.4. The method of obtaining the compounds of formula (I) according to claim 1 or one of its salts, characterized in that it is released from one of its functional derivatives by treatment with an appropriate solvolysis or hydrogenolysis agent,
or a peptide of formula (II): H-Z-OH,
where Z denotes -ARg-B-Asp-DE; -B-Asp-DE-Arg; -Asp-DE-Arg-BDE-Arg-B-Asp- or E-Arg-B-Asp-D-,
or a reactive derivative of such a peptide is treated with a cyclizing agent;
and / or a basic or acidic compound of formula (I) is converted into one of its salts by treatment with an acid or base.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4310643A DE4310643A1 (en) | 1993-04-01 | 1993-04-01 | Cyclic adhesion inhibitors |
| DEP4310643.9 | 1993-04-01 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU94011276A true RU94011276A (en) | 1997-11-10 |
| RU2130030C1 RU2130030C1 (en) | 1999-05-10 |
Family
ID=6484433
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU94011276A RU2130030C1 (en) | 1993-04-01 | 1994-03-31 | Cyclopeptides, a method of their synthesis, pharmaceutical compositions containing their and a method of their preparing |
Country Status (20)
| Country | Link |
|---|---|
| US (2) | US5849692A (en) |
| EP (1) | EP0632053B1 (en) |
| JP (1) | JP3694332B2 (en) |
| KR (1) | KR100304201B1 (en) |
| CN (1) | CN1056851C (en) |
| AT (1) | ATE184288T1 (en) |
| AU (1) | AU684489B2 (en) |
| CA (1) | CA2120303C (en) |
| CZ (1) | CZ286768B6 (en) |
| DE (2) | DE4310643A1 (en) |
| DK (1) | DK0632053T3 (en) |
| ES (1) | ES2138632T3 (en) |
| GR (1) | GR3032074T3 (en) |
| HU (1) | HUT69726A (en) |
| NO (1) | NO313756B1 (en) |
| PL (1) | PL178791B1 (en) |
| RU (1) | RU2130030C1 (en) |
| SK (1) | SK281828B6 (en) |
| TW (1) | TW343198B (en) |
| UA (1) | UA34436C2 (en) |
Families Citing this family (43)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5753230A (en) * | 1994-03-18 | 1998-05-19 | The Scripps Research Institute | Methods and compositions useful for inhibition of angiogenesis |
| DE4415310A1 (en) * | 1994-04-30 | 1995-11-02 | Merck Patent Gmbh | Cyclopeptides |
| US7053041B1 (en) | 1996-05-31 | 2006-05-30 | The Scripps Research Institute | Methods and compositions useful for inhibition of αvβ5mediated angiogenesis |
| DE19534016A1 (en) * | 1995-09-14 | 1997-03-20 | Merck Patent Gmbh | Biotin derivatives |
| DE19534177A1 (en) * | 1995-09-15 | 1997-03-20 | Merck Patent Gmbh | Cyclic adhesion inhibitors |
| DE19538741A1 (en) * | 1995-10-18 | 1997-04-24 | Merck Patent Gmbh | Cyclopeptide derivatives |
| DE19613933A1 (en) * | 1996-04-06 | 1997-10-09 | Merck Patent Gmbh | Cyclic adhesion inhibitors |
| AU738782B2 (en) | 1996-05-31 | 2001-09-27 | Scripps Research Institute, The | Methods and compositions useful for inhibition of alphavbeta5 mediated angiogenesis |
| DE19736772A1 (en) * | 1997-08-23 | 1999-02-25 | Merck Patent Gmbh | New guanidino-substituted bi:cyclic peptide compounds |
| AU2713500A (en) | 1998-12-23 | 2000-07-31 | G.D. Searle & Co. | Method of using a matrix metalloproteinase inhibitor and one or more antineoplastic agents as a combination therapy in the treatment of neoplasia |
| UA71608C2 (en) * | 1999-03-11 | 2004-12-15 | Merck Patent Gmbh | A method for producing the cyclic pentapeptide |
| DE19933173A1 (en) | 1999-07-15 | 2001-01-18 | Merck Patent Gmbh | Cyclic peptide derivatives as inhibitors of the integrin alpha¶v¶beta¶6¶ |
| US6359015B1 (en) | 2000-02-28 | 2002-03-19 | The United States Of America As Represented By The Department Of Veterans Affairs | Method for antagonizing inhibition effects of alcohol on cell adhesion |
| US6624187B1 (en) * | 2000-06-12 | 2003-09-23 | Health Research, Inc. | Long wave length absorbing bacteriochlorin alkyl ether analogs |
| DE10040105A1 (en) | 2000-08-17 | 2002-02-28 | Merck Patent Gmbh | Peptide and peptide mimetic derivatives with integrin inhibitor properties |
| FR2814744B1 (en) | 2000-10-04 | 2002-11-29 | Commissariat Energie Atomique | CYCLOPEPTIDES, THEIR PREPARATION PROCESS AND THEIR USE AS ANGIOGENESIS INHIBITOR OR ACTIVATOR |
| MXPA03007878A (en) * | 2001-03-02 | 2004-07-08 | Medimmune Inc | Methods of preventing or treating inflammatory or autoimmune disorders by administering integrin alphav beta3 antagonists. |
| US7879267B2 (en) * | 2001-08-02 | 2011-02-01 | J&J Vision Care, Inc. | Method for coating articles by mold transfer |
| JP2005533001A (en) * | 2002-03-04 | 2005-11-04 | メディミューン，インコーポレーテッド | Method for preventing or treating cancer in which integrin αvβ3 antagonist is administered in combination with other substances |
| AU2003213682C1 (en) * | 2002-03-04 | 2008-06-12 | Medimmune, Inc. | Methods of preventing or treating disorders by administering an integrin alphavbeta3 antagonist in combination with an HMG-CoA reductase inhibitor or a bisphosphonate |
| CA2481747A1 (en) | 2002-04-12 | 2003-10-23 | Medimmune, Inc. | Recombinant anti-interleukin-9 antibodies |
| GB0217017D0 (en) * | 2002-07-23 | 2002-08-28 | Bioacta Ltd | Peptide 2 |
| ITRM20020402A1 (en) * | 2002-07-29 | 2004-01-29 | Sigma Tau Ind Farmaceuti | FLUORO-ALCHIL-CYCLOPEPTIDES DERIVATIVES WITH ANTI-INTEGRINE ACTIVITIES. |
| US6977272B2 (en) * | 2002-10-16 | 2005-12-20 | President And Fellows Of Harvard College | Method for antagonizing inhibition effects of alcohol on cell adhesion |
| WO2004066956A2 (en) * | 2003-01-30 | 2004-08-12 | Medimmune, Inc. | Uses of integrin alphavbeta3 antagonists |
| KR20120035234A (en) * | 2003-04-11 | 2012-04-13 | 메디뮨 엘엘씨 | Recombinant il-9 antibodies and uses thereof |
| US7351739B2 (en) * | 2004-04-30 | 2008-04-01 | Wellgen, Inc. | Bioactive compounds and methods of uses thereof |
| ITRM20040239A1 (en) * | 2004-05-13 | 2004-08-13 | Sigma Tau Ind Farmaceuti | CYCLOPEPTIDIC DERIVATIVES FOR ANTI-INTEGRINE ACTIVITIES. |
| CA2585717A1 (en) | 2004-10-27 | 2006-05-04 | Medimmune Inc. | Modulation of antibody specificity by tailoring the affinity to cognate antigens |
| AU2007272970C1 (en) | 2006-07-11 | 2013-01-10 | Roy C. Levitt | Rhinosinusitis prevention and therapy with proinflammatory cytokine inhibitors |
| AU2007284690A1 (en) | 2006-08-10 | 2008-02-21 | Roy C. Levitt | Localized therapy of lower airways inflammatory disorders with proinflammatory cytokine inhibitors |
| US7842662B2 (en) | 2006-11-10 | 2010-11-30 | Cara Therapeutics, Inc. | Synthetic peptide amide dimers |
| US8236766B2 (en) | 2006-11-10 | 2012-08-07 | Cara Therapeutics, Inc. | Uses of synthetic peptide amides |
| BRPI0718651B8 (en) | 2006-11-10 | 2021-05-25 | Cara Therapeutics Inc | synthetic peptide amides |
| US7713937B2 (en) | 2006-11-10 | 2010-05-11 | Cara Therapeutics, Inc. | Synthetic peptide amides and dimeric forms thereof |
| US8906859B2 (en) | 2006-11-10 | 2014-12-09 | Cera Therapeutics, Inc. | Uses of kappa opioid synthetic peptide amides |
| EP2259768B1 (en) * | 2008-04-08 | 2019-05-22 | Merck Patent GmbH | Compositions containing cyclic peptides and methods of use |
| JP5773495B2 (en) * | 2008-10-23 | 2015-09-02 | ステバ バイオテック、エス．エイ． | RGD-containing peptidomimetics and uses thereof |
| CN101906141B (en) * | 2009-06-02 | 2013-04-17 | 首都医科大学 | Conjugates of one class of peptide chain and double fatty alcohol chains as well as preparation method and application thereof |
| CN101906144B (en) * | 2009-06-03 | 2013-06-19 | 首都医科大学 | Conjugate formed by conjugating one Arg-Gly-Asp-Val chain and two fatty alcohol chains by Asp, synthesis thereof and medical application thereof |
| RU2655763C2 (en) * | 2016-10-24 | 2018-05-29 | Общество С Ограниченной Ответственностью "Айвикс" | Pharmaceutical composition and method for treating female sexual dysfunctions |
| RU2626002C1 (en) | 2016-10-24 | 2017-07-21 | Общество С Ограниченной Ответственностью "Айвикс" | New group of peptides for treatment of female sexual dysfunction |
| US10494403B2 (en) | 2018-03-06 | 2019-12-03 | Ciphore Biomed Technology Limited Company | Cyclopeptide, pharmaceutical or cosmetic composition comprising the same and method for preparing the same |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4472305A (en) * | 1983-05-17 | 1984-09-18 | Sterling Drug Inc. | Hexapeptide amides |
| JP2945680B2 (en) * | 1988-09-09 | 1999-09-06 | 旭硝子株式会社 | Peptide derivatives and their uses |
| US5192746A (en) * | 1990-07-09 | 1993-03-09 | Tanabe Seiyaku Co., Ltd. | Cyclic cell adhesion modulation compounds |
| JPH04264097A (en) * | 1991-02-16 | 1992-09-18 | Asahi Glass Co Ltd | Peptide derivative and it's use |
| HUT63609A (en) * | 1992-03-10 | 1993-09-28 | Sandoz Ag | Process for producing new derivatives and isosters of beta-amino acids and pharmaceutical compositions comprising such compounds |
| UA43823C2 (en) * | 1992-07-06 | 2002-01-15 | Мерк Патент Геселлшафт Міт Бесшренктер Хафтунг | PHARMACEUTICAL COMPOSITION FOR INTEGRIN INHIBITION <font face = "Symbol"> a </font> <sub> V </sub> <font face = "Symbol"> b </font> <sub> 3 </sub> cell adhesion mammal WAY treatment and prevention of diseases associated with cell adhesion DISORDERS, METHOD FOR BINDING LOCK integrin fibrinogen, a composition for wound healing |
| US5753230A (en) * | 1994-03-18 | 1998-05-19 | The Scripps Research Institute | Methods and compositions useful for inhibition of angiogenesis |
-
1993
- 1993-04-01 DE DE4310643A patent/DE4310643A1/en not_active Withdrawn
-
1994
- 1994-03-02 UA UA94005107A patent/UA34436C2/en unknown
- 1994-03-21 EP EP94104396A patent/EP0632053B1/en not_active Expired - Lifetime
- 1994-03-21 DE DE59408715T patent/DE59408715D1/en not_active Expired - Lifetime
- 1994-03-21 DK DK94104396T patent/DK0632053T3/en active
- 1994-03-21 AT AT94104396T patent/ATE184288T1/en active
- 1994-03-21 ES ES94104396T patent/ES2138632T3/en not_active Expired - Lifetime
- 1994-03-25 CZ CZ1994704A patent/CZ286768B6/en not_active IP Right Cessation
- 1994-03-29 NO NO19941152A patent/NO313756B1/en not_active IP Right Cessation
- 1994-03-30 CA CA002120303A patent/CA2120303C/en not_active Expired - Lifetime
- 1994-03-30 AU AU59185/94A patent/AU684489B2/en not_active Expired
- 1994-03-30 CN CN94103298A patent/CN1056851C/en not_active Expired - Lifetime
- 1994-03-30 TW TW083102761A patent/TW343198B/en active
- 1994-03-31 SK SK383-94A patent/SK281828B6/en unknown
- 1994-03-31 KR KR1019940006639A patent/KR100304201B1/en not_active IP Right Cessation
- 1994-03-31 JP JP09682994A patent/JP3694332B2/en not_active Expired - Lifetime
- 1994-03-31 HU HU9400937A patent/HUT69726A/en unknown
- 1994-03-31 PL PL94302854A patent/PL178791B1/en unknown
- 1994-03-31 RU RU94011276A patent/RU2130030C1/en active
-
1996
- 1996-03-15 US US08/616,770 patent/US5849692A/en not_active Expired - Lifetime
-
1998
- 1998-10-01 US US09/164,585 patent/US6169072B1/en not_active Expired - Lifetime
-
1999
- 1999-12-08 GR GR990403165T patent/GR3032074T3/en unknown
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