RU2001126403A - LOW-MOLECULAR PEPTIDE DERIVATIVES AS LAMININ / NIDOGEN INTERACTION INHIBITORS - Google Patents

LOW-MOLECULAR PEPTIDE DERIVATIVES AS LAMININ / NIDOGEN INTERACTION INHIBITORS

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Publication number
RU2001126403A
RU2001126403A RU2001126403/04A RU2001126403A RU2001126403A RU 2001126403 A RU2001126403 A RU 2001126403A RU 2001126403/04 A RU2001126403/04 A RU 2001126403/04A RU 2001126403 A RU2001126403 A RU 2001126403A RU 2001126403 A RU2001126403 A RU 2001126403A
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Russia
Prior art keywords
alkyl
het
substituted
group
compound
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RU2001126403/04A
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Russian (ru)
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RU2262509C2 (en
Inventor
Ханс Ульрих ШТИЛЬЦ
Мартин ГЕРЛЬ
Гэри А ФЛИНН
Магда СТАНКОВА
Роберт А БИННИ
Original Assignee
Авентис Фарма Дойчланд Гмбх
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Priority claimed from EP99103869A external-priority patent/EP1070727A1/en
Application filed by Авентис Фарма Дойчланд Гмбх filed Critical Авентис Фарма Дойчланд Гмбх
Publication of RU2001126403A publication Critical patent/RU2001126403A/en
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Publication of RU2262509C2 publication Critical patent/RU2262509C2/en

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Claims (8)

1. Соединение формулы I1. The compound of formula I
Figure 00000001
Figure 00000001
 в которой R1 обозначает группу одной из нижеприведенных формулin which R1 denotes a group of one of the following formulas
Figure 00000002
Figure 00000002
Figure 00000003
Figure 00000003
Figure 00000004
Figure 00000004
Figure 00000005
Figure 00000005
Figure 00000006
Figure 00000006
Figure 00000007
Figure 00000007
Figure 00000008
Figure 00000008
Figure 00000009
Figure 00000009
 где R4 обозначает -A, -NH2, -NHR, -NR2, А2, -NHR1,where R4 is —A, —NH 2 , —NHR, —NR 2 , A 2 , —NHR1,
Figure 00000010
Figure 00000010
Figure 00000011
Figure 00000011
Figure 00000012
Figure 00000012
 R5 обозначает -(CH2)lCOOA, -(СН2)lCONH2, -(CH2)lNH2 или (СН2)l-SO3Н,R5 is - (CH 2 ) l COOA, - (CH 2 ) l CONH 2 , - (CH 2 ) l NH 2 or (CH 2 ) l -SO 3 H,
Figure 00000013
Figure 00000013
 Х обозначает группу, описываемую одной из следующих формулX denotes a group described by one of the following formulas
Figure 00000015
Figure 00000015
Figure 00000016
Figure 00000016
Figure 00000017
Figure 00000017
Figure 00000018
Figure 00000018
Figure 00000019
Figure 00000019
Figure 00000020
Figure 00000020
Figure 00000021
Figure 00000021
Figure 00000022
Figure 00000022
 где Y обозначает О, S, -N (А)-СО- или -(СН2)r-;where Y is O, S, —N (A) —CO— or - (CH 2 ) r -; D обозначает (СН2)r, О, S, NH, NR, (CH2)r-O, (CH2)r-S, (CH2)r-NH или (CH2)r-NR;D is (CH 2 ) r , O, S, NH, NR, (CH 2 ) r —O, (CH 2 ) r —S, (CH 2 ) r —NH or (CH 2 ) r —NR; R2 обозначает -А, -Е-ОН, -Е-СООН или -E-CONH2, где Е обозначает линейную или разветвленную C1-C10-алкильную цепь, которая может быть незамещенной или замещенной -А, -(СН2)m-ОН, -(СН2)m-СООН, -(CH2)m-C(O)NA2 или C5-C10-циклоалкильной группой, или Е обозначает С5-С10-циклоалкил, который может быть незамещенным или замещенным -А, -(СН2)m-ОН, -(СН2)m-COOH, -(CH2)m-C(O)NA2 или С5-С10-циклоалкильной группой;R2 is —A, —E — OH, —E — COOH or —E — CONH 2 , where E is a straight or branched C 1 -C 10 alkyl chain which may be unsubstituted or substituted with —A, - (CH 2 ) m —OH, - (CH 2 ) m —COOH, - (CH 2 ) m —C (O) NA 2 or a C 5 -C 10 cycloalkyl group, or E is a C 5 -C 10 cycloalkyl, which may be unsubstituted or substituted by —A, - (CH 2 ) m —OH, - (CH 2 ) m —COOH, - (CH 2 ) m —C (O) NA 2 or a C 5 -C 10 cycloalkyl group; R3 представляет собой группу одной из нижеприведенных формул:R3 represents a group of one of the following formulas:
Figure 00000023
Figure 00000023
Figure 00000024
Figure 00000024
Figure 00000025
Figure 00000025
 где R6 обозначает -Н, -СООН, -CONH2, -CONHR, -CONR2, -СН2OH илиwhere R6 is —H, —COOH, —CONH 2 , —CONHR, —CONR 2 , —CH 2 OH, or
Figure 00000026
Figure 00000026
Figure 00000027
Figure 00000027
Figure 00000028
Figure 00000028
 R7 обозначает линейную или разветвленную C1-C10-алкильную группу, которая может быть незамещенной или замещенной группами -А, -(СН2)m-ОН, -(СН2)m-СООН, -(СН2)m-C(O)NA2 или C5-С10-циклоалкильной группой, или R7 обозначает С5-С10-циклоалкильную группу, которая может быть незамещенной или замещенной группами -А, -(СН2)m-ОН, -(СН2)m-СООН, -(СН2)m-С (O)NA2 или С5-С10-циклоалкильной группой;R7 is a linear or branched C 1 -C 10 -alkyl group which may be unsubstituted or substituted by —A, - (CH 2 ) m —OH, - (CH 2 ) m —COOH, - (CH 2 ) m —C (O) NA 2 or a C 5 -C 10 cycloalkyl group, or R7 is a C 5 -C 10 cycloalkyl group which may be unsubstituted or substituted by —A, - (CH 2 ) m —OH, - (CH 2 ) m —COOH, - (CH 2 ) m —C (O) NA 2 or a C 5 -C 10 cycloalkyl group; R обозначает разветвленный или неразветвленный C1-C6-алкил, С2-С6-алкенил, С2-С6-алкинил, С5-С10-циклоалкил, Het или Ar, которые необязательно могут быть замещены одним или более атомами галогена, C1-С6-алкилокси, разветвленной или неразветвленной C1-С6-алкильной, С2-С6-алкенильной, С2-С6-алкинильной или С5-С10-циклоалкильной группами, или -C1-C6-алкил-Het, -C1-С6-алкил-Ar, -O-C1-C6-алкил-Het, -O-C1-С6-алкил-Ar, Het или Ar, где Het обозначает моноциклическое или бициклическое, 5-10-членное ароматическое или неароматическое кольцо, содержащее 1 или 2 одинаковых или разных гетероатома в качестве членов указанного кольца, выбранных из группы, состоящей из азота, кислорода и серы, которое может быть незамещенным или замещенным одной или более гидрокси- или карбоксигруппами; Ar обозначает моноциклическое или бициклическое, 5-10-членное ароматическое кольцо, которое может быть незамещенным или замещенным одной или более гидрокси- или карбоксигруппами;R is branched or unbranched C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 5 -C 10 cycloalkyl, Het or Ar, which may optionally be substituted with one or more atoms halogen, C 1 -C 6 alkyloxy, branched or unbranched C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl or C 5 -C 10 cycloalkyl groups, or -C 1 -C 6 -alkyl-Het, -C 1 -C 6 -alkyl-Ar, -OC 1 -C 6 -alkyl-Het, -OC 1 -C 6 -alkyl-Ar, Het or Ar, where Het is monocyclic or a bicyclic, 5-10 membered aromatic or non-aromatic ring containing 1 or 2 identical X or different heteroatoms as members of said ring, selected from the group consisting of nitrogen, oxygen and sulfur, which may be unsubstituted or substituted with one or more hydroxy or carboxy groups; Ar is a monocyclic or bicyclic, 5-10 membered aromatic ring, which may be unsubstituted or substituted by one or more hydroxy or carboxy groups; Z обозначает (СН2)m, O, S, NH, NR, N-C(O)-R или NSO2R;Z is (CH 2 ) m , O, S, NH, NR, NC (O) -R or NSO 2 R; А обозначает Н или С1-С4-алкил;A is H or C 1 -C 4 alkyl; l, m и r = 0-3;l, m and r = 0-3; n и k = 1-2;n and k = 1-2; р = 0-1;p is 0-1; q = 1-3,q = 1-3, и все его стереоизомерные формы и их смеси во всех соотношениях, включая их физиологически толерантные соли.and all its stereoisomeric forms and mixtures thereof in all ratios, including their physiologically tolerant salts. 2. Соединение формулы I по п.1, отличающееся тем, что n=1.2. The compound of formula I according to claim 1, characterized in that n = 1. 3. Соединение формулы I по п.1 или 2, отличающееся тем, что R в группе Х обозначает Het или Ar, которые могут быть необязательно замещены группами -C1-C6-алкил-Het, -C1-С6-алкил-Ar, -О-С1-С6-алкил-Het, -O-C1-C6-алкил-Ar, Het или Ar.3. The compound of formula I according to claim 1 or 2, characterized in that R in group X is Het or Ar, which may optionally be substituted with —C 1 -C 6 -alkyl-Het, -C 1 -C 6 -alkyl groups -Ar, -O-C 1 -C 6 -alkyl-Het, -OC 1 -C 6 -alkyl-Ar, Het or Ar. 4. Фармацевтическая композиция, содержащая, по меньшей мере, одно соединение по одному или более из предшествующих пунктов и/или его физиологически толерантные соли.4. A pharmaceutical composition comprising at least one compound according to one or more of the preceding paragraphs and / or physiologically tolerant salts thereof. 5. Соединение по одному или более из пп.1-3 и/или его физиологически толерантные соли, предназначенные для использования в качестве фармацевтического средства.5. The compound according to one or more of claims 1 to 3 and / or its physiologically tolerant salts intended for use as a pharmaceutical agent. 6. Способ идентификации соединения, которое ингибирует взаимодействие ламинина и нидогена, отличающийся тем, что в качестве конкурентного ингибитора используют соединение по пп.1-3.6. A method for identifying a compound that inhibits the interaction of laminin and nidogen, characterized in that the compound according to claims 1 to 3 is used as a competitive inhibitor. 7. Способ по п.6, отличающийся тем, что он включает также приготовление композиции на основе идентифицированного соединения в фармацевтически приемлемой форме.7. The method according to claim 6, characterized in that it also includes the preparation of a composition based on the identified compound in a pharmaceutically acceptable form. 8. Способ получения фармацевтической композиции, включающий способ по п.6, а также смешивание идентифицированного соединения и/или его физиологически толерантной соли с фармацевтически приемлемым носителем.8. A method of obtaining a pharmaceutical composition comprising the method according to claim 6, as well as mixing the identified compound and / or its physiologically tolerant salt with a pharmaceutically acceptable carrier.
RU2001126403/04A 1999-03-01 2000-02-19 Low-molecular peptide derivatives as inhibitors in interaction laminine/nidogen RU2262509C2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP99103869A EP1070727A1 (en) 1999-03-01 1999-03-01 Low molecular weight peptide derivatives as inhibitors of the laminin/nidogen interaction
EP99103869.6 1999-03-01

Related Child Applications (1)

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RU2005114905/04A Division RU2380371C2 (en) 1999-03-01 2000-02-19 Low-molecular derivatives of peptides as inhibitors of laminin/nidogen reaction

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RU2001126403A true RU2001126403A (en) 2003-07-20
RU2262509C2 RU2262509C2 (en) 2005-10-20

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US (1) US6365572B1 (en)
EP (4) EP1070727A1 (en)
JP (1) JP4542272B2 (en)
CN (2) CN1237075C (en)
AT (2) ATE477271T1 (en)
AU (1) AU779779B2 (en)
BR (1) BR0008647A (en)
CA (1) CA2363958C (en)
CY (1) CY1106967T1 (en)
CZ (1) CZ300736B6 (en)
DE (2) DE60036087T2 (en)
DK (1) DK1157040T3 (en)
ES (1) ES2288844T3 (en)
HK (2) HK1042499A1 (en)
HU (1) HU228993B1 (en)
ID (1) ID30183A (en)
PL (2) PL208356B1 (en)
PT (1) PT1157040E (en)
RU (2) RU2380371C2 (en)
TR (2) TR200800782T2 (en)
WO (1) WO2000052051A1 (en)
ZA (1) ZA200106972B (en)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1070727A1 (en) * 1999-03-01 2001-01-24 Aventis Pharma Deutschland GmbH Low molecular weight peptide derivatives as inhibitors of the laminin/nidogen interaction
WO2001032926A2 (en) * 1999-11-01 2001-05-10 Curagen Corporation Differentially expressed genes involved in angiogenesis, the polypeptides encoded thereby, and methods of using the same
US20080241835A1 (en) * 1999-11-01 2008-10-02 Genentech, Inc. Differentially expressed genes involved in angiogenesis, the polypeptides encoded thereby, and methods of using the same
US7407660B2 (en) 2003-04-16 2008-08-05 Genentech, Inc. Methods and compositions for selective modulation of vascularization
FR2947452B1 (en) * 2009-07-01 2012-04-20 Fabre Pierre Dermo Cosmetique L-SERINE AND / OR L-ASPARAGINE AND / OR L-VALINE FOR PREVENTING AND / OR TREATING INFLAMMATORY SKIN REACTIONS.
RU2622018C1 (en) * 2016-06-16 2017-06-08 федеральное государственное автономное образовательное учреждение высшего образования "Российский университет дружбы народов" (РУДН) Quickly dissolving transbuccal film for depressive disorders, anxiety and adaptation disorders treatment
EP3551608A1 (en) * 2016-12-09 2019-10-16 Celtaxsys Inc. Pendant amines and derivatives as inhibitors of leukotriene a4 hydrolase

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5493008A (en) * 1994-08-15 1996-02-20 The University Of Virginia Patent Foundation Two non-contiguous regions contribute to nidogen binding to a single EGF-like motif of the laminin γ1 chain
DE19701607A1 (en) 1997-01-17 1998-07-23 Hoechst Ag Antibodies that bind to the nidogen-binding domain of laminin, their production and use
EP1070727A1 (en) * 1999-03-01 2001-01-24 Aventis Pharma Deutschland GmbH Low molecular weight peptide derivatives as inhibitors of the laminin/nidogen interaction

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