CN1195778C - 细胞粘附抑制剂 - Google Patents
细胞粘附抑制剂 Download PDFInfo
- Publication number
- CN1195778C CN1195778C CNB961963808A CN96196380A CN1195778C CN 1195778 C CN1195778 C CN 1195778C CN B961963808 A CNB961963808 A CN B961963808A CN 96196380 A CN96196380 A CN 96196380A CN 1195778 C CN1195778 C CN 1195778C
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- China
- Prior art keywords
- methyl
- amino
- carbonyl
- propyl
- ethyl
- Prior art date
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Classifications
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- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
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- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
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- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
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- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
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- C07K5/1005—Tetrapeptides with the first amino acid being neutral and aliphatic
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Abstract
Description
化合物# | Z | A1 | A2 | (A3)n | X |
1 | 3-甲氧基-4-(N′-苯基脲)苯基乙酰基 | L | D | V/P | OH |
2 | 3-甲氧基-4-(N′-苯基脲)苯基乙酰基 | M | D | V/P | OH |
3 | 6-甲氧基-5-(N′-(2-甲基苯基)-脲)-2-吡啶基乙酰基 | L | D | V | NH2 |
4 | 6-甲氧基-5-(N′-(2-甲基苯基)-脲)-2-吡啶基乙酰基 | L | D | V | OH |
5 | 3-异喹啉羰基 | L | E | V | OH |
6 | 3-异喹啉羰基 | L | 羟基氨基羰基甲基 | V | OH |
7 | 3-异喹啉羰基 | L | S | V | OH |
8 | 3-异喹啉羰基 | L | (N-Bn)-H | V | OH |
9 | 3-异喹啉羰基 | L | C | V | OH |
10 | 3-异喹啉羰基 | L | 四唑-5-基-甲基 | V | OH |
化合物# | Z | A1 | A2 | (A3)n | X |
11 | 3-异喹啉羰基 | L | D | ----- | NH-CyM |
12 | 3-异喹啉羰基 | L | D | ----- | OH |
13 | 3-(4-羟基苯基)丙酰基 | L(R2=Me) | D | V | OMe |
14 | 3-(4-羟基苯基)丙酰基 | L | D | ----- | NH-CyM |
15 | 3-(4-羟基苯基)丙酰基 | L | d | ----- | NHi-Bu |
16 | 3-(4-羟基苯基)丙酰基 | I | d | ----- | NHi-Bu |
17 | 3-(4-羟基苯基)丙酰基 | I | D | ----- | NHi-Bu |
18 | 3-(4-羟基苯基)丙酰基 | (N-Me)-L | D | V | OMe |
19 | 3-(4-羟基苯基)丙酰基 | L | D | V | OMe |
20 | 3-(4-羟基苯基)丙酰基 | L | D | (N-Me)-V | OMe |
21 | 3-(4-羟基苯基)丙酰基 | L | 1-羧基-乙基 | V | OMe |
22 | 3-(4-羟基苯基)丙酰基 | L | (N-Me)-D | V | OMe |
23 | 四氢-3-异喹啉羰基 | L | D | ----- | OH |
24 | 3-苯基丙酰基 | L | D | ----- | NH-CyM |
25 | 4-苯基丁酰基 | L | D | ----- | NH-CyM |
26 | 5-苯基戊酰基 | L | D | ----- | NH-CyM |
27 | 四氢-3-异喹啉羰基 | L | (N-Bn)-H | V | OH |
28 | 乙酰基 | (N-Bn)-L | D | V | OMe |
29 | 乙酰基 | (N-苯乙基)-L | D | V | OMe |
30 | 3-苯基丙酰基 | (N-苯乙基)-L | D | V | OMe |
31 | 四氢-3-异喹啉羰基 | L | E | V | OH |
32 | 3-异喹啉羰基 | L | D | V/P | OH |
33 | 四氢-3-异喹啉羰基 | L | D | V/P | OH |
34 | 苯基乙酰基 | L | D | V/P | OH |
35 | 苯基乙酰基 | L | D | V/P | OMe |
36 | 3-苯基丙酰基 | L | D | V/P | OH |
37 | 3-苯基丙酰基 | L | D | V/P | OMe |
化合物# | Z | A1 | A2 | (A3)n | X |
38 | 3-(4-羟基苯基)丙酰基 | L | D | V/P | OH |
39 | 3-(4-羟基苯基)丙酰基 | L | D | V/P | OMe |
40 | Boc | L | D | V/P | OMe |
41 | 2-喹啉羰基 | L | D | V/P | OMe |
42 | 苯基乙酰基 | L | D | V/2-甲基哌啶基 | OH |
43 | 苯基乙酰基 | L | D | V/正丁基 | OH |
44 | 2-喹啉羰基 | L | D | V/正丁基 | OH |
45 | 4-甲氧基苯基乙酰基 | (N-Me)-L | D | V | NHMe |
46 | 3-(4-羟基苯基)丙酰基 | (N-Me)-L | D | V | NHMe |
47 | 苄基氨基羰基 | L | D | V | NHMe |
48 | 对-甲苯基氨基羰基 | L | D | V | NHMe |
49 | 苯基乙酰基 | 正丙基 | D | V | NHMe |
50 | 苯基乙酰基 | L | D | V | NHNap |
51 | 苯基乙酰基 | L | D | 正丙基 | NHMe |
52 | 2-喹啉羰基 | L | D | 正丙基 | NHMe |
53 | 苯基乙酰基 | L | D | 2-丁基 | NH2 |
54 | 苯基乙酰基 | L | D | 2-丁基 | OMe |
55 | 苯基乙酰基 | L | D | 2-丁基 | NHMe |
56 | 2-喹啉羰基 | L | D | 2-丁基 | OMe |
57 | 2-喹啉羰基 | L | D | 2-丁基 | NHMe |
58 | 1,2,3,4-四氢-2-喹啉羰基 | L | D | 2-丁基 | NHMe |
59 | 2-喹啉羰基 | L | D | (O-Me)-T | NHMe |
60 | 2-喹啉羰基 | L | D | T | NHt-Bu |
61 | 2-喹啉羰基 | L | D | T | 吗啉代 |
62 | Boc | L | D | T | NHt-Bu |
化合物# | Z | A1 | A2 | (A3)n | X |
63 | 2-N-Boc-氨基-1,2,3,-4-四氢-2-萘甲酰基 | L | D | V | OH |
64 | 3-苯基丙酰基 | L | D | V | OH |
65 | 3-(4-羟基苄基)-2-双-(甲基磺酰基)氨基丙酰基 | L | D | V | OH |
66 | 3-(4-羟基苯基)-2-N-Boc-氨基丙酰基 | L | D | V | OH |
67 | 2-氨基-1,2,3,4-四氢-2-萘甲酰基TFA盐 | L | D | V | OH |
68 | Boc | D | V | ----- | OH |
69 | 3-异喹啉羰基 | L | D | V | OH |
70 | 3-异喹啉羰基 | D | V | ----- | OH |
71 | 1,2,3,4-四氢-3-异喹啉羰基 | D | V | ----- | OH |
72 | 萘甲酰基 | L | D | V | OH |
73 | 1,2,3,4-四氢-2-萘甲酰基 | L | D | V | OH |
74 | 萘甲酰基 | D | V | ----- | OH |
75 | 1,2,3,4-四氢-2-萘甲酰基 | D | V | ----- | OH |
76 | 5-苯基戊酰基 | D | V | ----- | OH |
77 | 2-吡啶羰基 | L | D | V | OH |
78 | 2-吡啶羰基 | D | V | ----- | OH |
79 | 3-四氢呋喃羰基 | L | D | V | OH |
80 | 2-四氢呋喃羰基 | L | D | V | OH |
81 | 3-异喹啉羰基 | F | D | V | OH |
82 | 3-异喹啉羰基 | A(R2=Me) | D | V | OH |
83 | 3-异喹啉羰基 | 环己基 | D | V | OH |
84 | 1,2,3,4-四氢-3-异喹啉羰基 | 环己基 | D | V | OH |
85 | 3-异喹啉羰基 | 环己基甲基 | D | V | OH |
86 | 1,2,3,4-四氢-3-异喹啉羰基 | 环己基甲基 | D | V | OH |
化合物# | Z | A1 | A2 | (A3)n | X |
87 | 3-异喹啉羰基 | D | F | ----- | OH |
88 | 1,2,3,4-四氢-3-异喹啉羰基 | D | L | ----- | OH |
89 | 3-异喹啉羰基 | D | L | ----- | OH |
90 | 1,2,3,4-四氢-3-异喹啉羰基 | L | D | L | OH |
91 | 3-异喹啉羰基 | L | D | L | OH |
92 | 1,2,3,4-四氢-3-异喹啉羰基 | L | D | F | OH |
93 | 3-异喹啉羰基 | L | D | F | OH |
94 | 2-喹啉羰基 | L | D | V | OH |
95 | 3,3,-二苯基丙酰基 | L | D | V | OH |
96 | 1,2,3,4-四氢-3-异喹啉羰基 | A | D | V | OH |
97 | 3-异喹啉羰基 | A | D | V | OH |
98 | 5-苯基戊酰基 | L | D | V | OH |
99 | 吲哚-2-羰基 | L | D | V | OH |
100 | 3-(4-羟基)苯基丙酰基 | L | D | ----- | NHi-Bu |
101 | 苯甲酰基 | L | D | ----- | NHi-Bu |
102 | 5-苯基戊酰基 | L | D | ----- | NHi-amyl |
103 | 3-(4-羟基)苯基丙酰基 | L | D | ----- | NHi-amyl |
104 | 6-苯基己酰基 | L | D | V | OH |
105 | 苯甲酰基 | L | D | V | OH |
106 | 5-苯基戊酰基 | L | D | ----- | NHi-Bu |
107 | N-苯基琥珀酰胺酰基 | L | D | V | OH |
108 | N-4-氟苯基琥珀酰胺酰基 | L | D | V | OH |
109 | N-甲基-N-苯基琥珀酰胺酰基 | L | D | V | OH |
110 | 1,2,3,4-四氢-2-喹啉羰基 | L | D | ----- | NHi-amyl |
111 | N-苯基琥珀酰胺酰基 | L | D | ----- | NHi-Bu |
112 | 3-苯基丙基 | (N-Me)-L | (O-Me)-D | V | OMe |
化合物# | Z | A1 | A2 | (A3)n | X |
113 | 苯甲酰基 | (N-Me)-L | D | V | OH |
114 | 1,2,3,4-四氢-2-喹啉羰基 | L | D | V | NHHex |
115 | 1,2,3,4-四氢-2-喹啉羰基 | L | D | V | 4-苯基哌啶 |
116 | 3-(4-羟基)苯基丙酰基 | L | D | ----- | NHHex |
117 | 3-(4-羟基)苯基丙酰基 | L | D | ----- | N(iBu)2 |
118 | 3-(4-羟基)苯基丙酰基 | L | D | ----- | N(iBu)2 |
119 | 3-(4-羟基)苯基丙酰基 | L | D | V | NHHex |
120 | 1,2,3,4-四氢-2-喹啉羰基 | L | D | V | NMePh |
121 | 2-喹啉羰基 | L | D | V | NMePh |
122 | 1,2,3,4-四氢-2-喹啉羰基 | L | D | V | NH-4-氟苯基 |
123 | 2-喹啉羰基 | L | D | V | NH-4-氟苯基 |
124 | 1,2,3,4-四氢-2-喹啉羰基 | L | D | V | NHPh |
125 | 2-喹啉羰基 | L | D | V | NHPh |
126 | 2-吡啶羰基 | (N-Me)-L | D | V | NHMe |
127 | 2-喹啉羰基 | L | D | V | 4-苯基哌嗪 |
128 | 4-甲氧基苯甲酰基 | (N-Me)-L | D | V | NHMe |
129 | 苯基乙酰基 | Y | D | V | NHMe |
130 | 苯基乙酰基 | P | D | V | NHMe |
131 | 苯基乙酰基 | R | D | V | NHMe |
132 | 苯基乙酰基 | N | D | V | NHMe |
133 | 2-N-Boc-氨基-1,2,3,4-四氢-2-萘甲酰基 | D | V | ----- | NHMe |
134 | 2-N-苯基乙酰基氨基-1,2,3,4-四氢-2-萘甲酰基 | D | V | ----- | NHMe |
135 | Boc | D | P | G | OH |
化合物# | Z | A1 | A2 | (A3)n | X |
136 | 苯基乙酰基 | D | P | G | OH |
137 | 苯基乙酰基 | L | D | ----- | N[双-(羧基)-甲基]-2-甲基哌啶酰氨基 |
138 | 苯基乙酰基 | L | D | P | NH-(双-(羧基)-甲基] |
139 | 苯基乙酰基 | L | D | ----- | N-[羧基甲基]-2-甲基哌啶酰胺 |
140 | 3-苯基丙酰基 | (N-Me)-L | D | V | OMe |
141 | 4-羟基苯基乙酰基 | (N-Me)-L | D | V | OMe |
142 | 2-喹啉羰基 | (N-Me)-L | D | V | OMe |
143 | 4-苯基丁酰基 | (N-Me)-L | D | V | OMe |
144 | 4-(N′-2-羟基-苯基脲)苯基乙酰基 | L | D | V/P | OH |
145 | PUPA | L | D | V/P | OH |
146 | 4-(N′-2-羟基-苯基脲)苯基乙酰基 | M | D | V/P | OH |
147 | 3-甲氧基-4-(N′苯基脲)苯基乙酰基 | L | D | V/P | NH2 |
148 | 2-MPUPA | L | D | V/P | NH2 |
149 | Boc | D | V | P | OH |
150 | 5-苯基戊酰基 | D | V | P | OH |
151 | 2-烯丙基-4-苯基丁酰基 | V | P | ----- | OH |
152 | 乙酰基 | F | L | D/V | OH |
153 | 苯甲酰基 | F | L | D/V | OH |
154 | 1,2,3,4-四氢-3-异喹啉羰基 | L | D | V | OMe |
155 | 4-苯基丁酰基 | L | D | V | OH |
化合物# | Z | A1 | A2 | (A3)n | X |
156 | 3-异喹啉羰基 | L | D | V | OMe |
157 | 3-异喹啉羰基 | L | D | ----- | NHi-Bu |
158 | 2-喹啉羰基 | L | D | V | Ot-Bu |
159 | 2-喹啉羰基 | L | (O-Bn)-D | V | OH |
160 | 2-喹啉羰基 | L | D | D | OH |
161 | 4-苯基丁酰基 | L | D | ----- | NHi-Bu |
162 | 3-苯基丙酰基 | L | D | ----- | NHi-Bu |
163 | 苯甲酰基 | G | L | D | NHi-Bu |
164 | 2-喹啉羰基 | L | D | V | NHMe |
165 | 4-甲氧基苯甲酰基 | L | D | ----- | NHi-Bu |
166 | 4-苯基丁酰基 | L | D | V | OMe |
167 | Boc | L | D | V/M | OMe |
168 | 2-喹啉羰基 | L | D | V/M | OMe |
169 | N-正丁基氨基羰基 | D | V | ----- | OMe |
170 | 2-喹啉羰基 | L | D | T | OMe |
171 | N-叔丁基氨基羰基 | L | D | ----- | NHi-Bu |
172 | 苯甲酰基 | G | D | V | OMe |
173 | 苯甲酰基 | G | (O-Me)-D | V | OMe |
174 | 2-喹啉羰基 | L | D | ----- | NH(1-羟基-甲基-2-甲基-丙基) |
175 | 2-喹啉羰基 | L | D | V | 吗啉代 |
176 | 4-甲氧基苯基乙酰基 | L | D | T | OMe |
177 | 4-甲氧基苯基磺酰基 | L | D | T | OMe |
178 | 2-喹啉羰基 | L | D | V | NH2 |
179 | 2-喹啉羰基 | (N-Me)-L | D | V | NHMe |
180 | 苯基乙酰基 | (N-Me)-L | D | V | NHMe |
181 | 苯基乙酰基 | L | D | V | NHMe |
化合物# | Z | A1 | A2 | (A3)n | X |
182 | 3-苯基丙酰基 | (N-Me)-L | D | V | NHMe |
183 | 苯基乙酰基 | M | D | V | NHMe |
184 | 3-苯基丙酰基 | (N-Me)-L | D | V | NHMe |
185 | 2-喹啉羰基 | L | D | A(R2=Me) | NHMe |
186 | 2-喹啉羰基 | L | D | V/M | OH |
187 | 苯基氨基羰基 | L | D | V | NHMe |
188 | 4-羟基苯基乙酰基 | (N-Me)-L | D | V | NHMe |
189 | 苯基磺酰基 | L | D | V | NHMe |
190 | 苯基乙酰基 | L | D | (O-Me)-T | OMe |
191 | 苯基乙酰基 | L | D | T | OMe |
192 | 苯基乙酰基 | L | D | (O-Bn)-T | OMe |
193 | 苯基乙酰基 | L | D | (O-Ac)-T | OMe |
194 | 苯基乙酰基 | V | D | V | NHMe |
195 | 2-喹啉羰基 | L | D | T | On-Bu |
196 | 苯基乙酰基 | L | D | V | On-Bu |
197 | 2-喹啉羰基 | L | D | T | NH(4-甲氧基苄基) |
198 | 2-喹啉羰基 | L | D | ----- | NH(3,3-二甲基正丁基) |
199 | PUPA | I | D | V/P | NH2 |
200 | PUPA | L | d | V/P | NH2 |
201 | PUPA | L | D | v/P | NH2 |
202 | 2-MPUPA | (N-6-氨基己酰基)-K | D | V/P | OH |
203 | PUPA | L | D | V | OH |
204 | PUPA | L | D | V | NHMe |
205 | PUPA | L | D | V | NHi-Bu |
206 | 2-MPUPA | L | D | V/P | OH |
化合物# | Z | A1 | A2 | (A3)n | X |
207 | 2-MPUPA | L | D | 苯基 | OH |
208 | PUPA | L | D | V/P | NH2 |
209 | PUPA | I | D | V/P | NH2 |
210 | PUPA | L | d | V/P | NH2 |
211 | PUPA | L | D | v/P | NH2 |
212 | PUPA | I | d | v/p | NH2 |
213 | PUPA | L | D | ----- | NHBn |
214 | PUPA | L | D | ----- | 吗啉代 |
215 | PUPA | L | D | ----- | NHi-Pr |
216 | PUPA | L | D | ----- | NHCy |
217 | PUPA | L | D | ----- | NHi-Bu |
218 | PUPA | L | D | ----- | 哌啶基 |
219 | 2-MPUPA | M | D | D | NH2 |
220 | 2-MPUPA | M | D | L | NH2 |
221 | 2-MPUPA | M | D | V | NH2 |
222 | 2-MPUPA | M | D | I | NH2 |
223 | 2-MPUPA | M | D | E | NH2 |
224 | 2-MPUPA | M | D | T | NH2 |
225 | 2-MPUPA | M | D | M | NH2 |
226 | 2-MPUPA | M | D | n | NH2 |
227 | 2-MPUPA | M | D | e | NH2 |
228 | 2-MPUPA | M | D | W | NH2 |
229 | 2-MPUPA | M | D | s | NH2 |
230 | 2-MPUPA | L | D | D | NH2 |
231 | 2-MPUPA | L | D | L | NH2 |
232 | 2-MPUPA | L | D | V | NH2 |
233 | 2-MPUPA | L | D | I | NH2 |
234 | 2-MPUPA | L | D | E | NH2 |
化合物# | Z | A1 | A2 | (A3)n | X |
235 | 2-MPUPA | L | D | T | NH2 |
236 | 2-MPUPA | L | D | M | NH2 |
237 | 2-MPUPA | L | D | n | NH2 |
238 | 2-MPUPA | L | D | e | NH2 |
239 | 2-MPUPA | L | D | W | NH2 |
240 | 2-MPUPA | L | D | s | NH2 |
241 | 2-MPUPA | P | D | D | NH2 |
242 | 2-MPUPA | P | D | L | NH2 |
243 | 2-MPUPA | P | D | V | NH2 |
244 | 2-MPUPA | P | D | I | NH2 |
245 | 2-MPUPA | P | D | E | NH2 |
246 | 2-MPUPA | P | D | T | NH2 |
247 | 2-MPUPA | P | D | M | NH2 |
248 | 2-MPUPA | P | D | n | NH2 |
249 | 2-MPUPA | P | D | e | NH2 |
250 | 2-MPUPA | P | D | W | NH2 |
251 | 2-MPUPA | P | D | s | NH2 |
252 | 2-MPUPA | T | D | D | NH2 |
253 | 2-MPUPA | T | D | L | NH2 |
254 | 2-MPUPA | T | D | V | NH2 |
255 | 2-MPUPA | T | D | I | NH2 |
256 | 2-MPUPA | T | D | E | NH2 |
257 | 2-MPUPA | T | D | T | NH2 |
258 | 2-MPUPA | T | D | M | NH2 |
259 | 2-MPUPA | T | D | n | NH2 |
260 | 2-MPUPA | T | D | e | NH2 |
261 | 2-MPUPA | T | D | W | NH2 |
262 | 2-MPUPA | T | D | s | NH2 |
263 | 2-MPUPA | E | D | D | NH2 |
化合物# | Z | A1 | A2 | (A3)n | X |
264 | 2-MPUPA | E | D | L | NH2 |
265 | 2-MPUPA | E | D | V | NH2 |
266 | 2-MPUPA | E | D | I | NH2 |
267 | 2-MPUPA | E | D | E | NH2 |
268 | 2-MPUPA | E | D | T | NH2 |
269 | 2-MPUPA | E | D | M | NH2 |
270 | 2-MPUPA | E | D | n | NH2 |
271 | 2-MPUPA | E | D | e | NH2 |
272 | 2-MPUPA | E | D | W | NH2 |
273 | 2-MPUPA | E | D | s | NH2 |
274 | 2-MPUPA | C | D | V | NH2 |
275 | 2-MPUPA | S | D | D | NH2 |
276 | 2-MPUPA | S | D | L | NH2 |
277 | 2-MPUPA | S | D | V | NH2 |
278 | 2-MPUPA | S | D | I | NH2 |
279 | 2-MPUPA | S | D | E | NH2 |
280 | 2-MPUPA | S | D | T | NH2 |
281 | 2-MPUPA | S | D | M | NH2 |
282 | 2-MPUPA | S | D | n | NH2 |
283 | 2-MPUPA | S | D | e | NH2 |
284 | 2-MPUPA | S | D | W | NH2 |
285 | 2-MPUPA | S | D | s | NH2 |
286 | 2-MPUPA | I | D | D | NH2 |
287 | 2-MPUPA | I | D | L | NH2 |
288 | 2-MPUPA | I | D | V | NH2 |
289 | 2-MPUPA | I | D | I | NH2 |
290 | 2-MPUPA | I | D | E | NH2 |
291 | 2-MPUPA | I | D | T | NH2 |
292 | 2-MPUPA | I | D | M | NH2 |
化合物# | Z | A1 | A2 | (A3)n | X |
293 | 2-MPUPA | I | D | n | NH2 |
294 | 2-MPUPA | I | D | e | NH2 |
295 | 2-MPUPA | I | D | W | NH2 |
296 | 2-MPUPA | I | D | s | NH2 |
297 | 2-MPUPA | Q | D | D | NH2 |
298 | 2-MPUPA | Q | D | L | NH2 |
299 | 2-MPUPA | Q | D | V | NH2 |
300 | 2-MPUPA | Q | D | I | NH2 |
301 | 2-MPUPA | Q | D | E | NH2 |
302 | 2-MPUPA | Q | D | T | NH2 |
303 | 2-MPUPA | Q | D | M | NH2 |
304 | 2-MPUPA | Q | D | n | NH2 |
305 | 2-MPUPA | Q | D | e | NH2 |
306 | 2-MPUPA | Q | D | W | NH2 |
307 | 2-MPUPA | Q | D | s | NH2 |
308 | 2-MPUPA | M | E | D | NH2 |
309 | 2-MPUPA | M | E | V | NH2 |
310 | 2-MPUPA | L | E | D | NH2 |
311 | 2-MPUPA | L | E | V | NH2 |
312 | 2-MPUPA | P | E | D | NH2 |
313 | 2-MPUPA | P | E | V | NH2 |
314 | 2-MPUPA | T | E | D | NH2 |
315 | 2-MPUPA | M | D | V/P | OH |
316 | 4-(N′-2-吡啶基脲)苯基乙酰基 | L | D | V/P | OH |
317 | 3-甲氧基-4-(N′-(2-甲基苯基)-脲)苯基乙酰基 | L | D | V/P | NH2 |
318 | PUPA | L | D | V | 吗啉代 |
319 | PUPA | L | D | V | NHi-Pr |
320 | PUPA | L | D | V | NHCy |
化合物# | Z | A1 | A2 | (A3)n | X |
321 | PUPA | L | D | V | NHBn |
322 | PUPA | L | D | V | 哌啶基 |
323 | PUPA | L | D | V | NHi-Bu |
324 | PUPA | L | D | V/P | NHCy |
325 | PUPA | L | D | V/P | 哌啶基 |
326 | PUPA | L | D | V/P | NHBn |
327 | PUPA | L | D | V/P | NHi-Pr |
328 | PUPA | L | D | V/P | NHi-Bu |
329 | 2-MPUPA | L | D | V | 吗啉代 |
330 | N-3-(4-羟基苯基) | 2-甲基哌啶基 | D | ----- | NHi-Bu |
331 | N-3-(4-羟基苯基)-丙酰基 | P | D | ----- | NHi-Bu |
332 | 3-异喹啉羰基 | L | (N-3-甲基-2-丁酰基)-N | ----- | OH |
333 | 4-甲基戊酰基 | D | ----- | ----- | NHCyM |
334 | Cbz | -CH2CH2-(NofA1) | (N-CH2CH2-(CofA1)-D | V | OMe |
335 | 3-(4-羟基苯基)丙酰基 | -CH2CH2-(NofA1) | (N-CH2CH2-(CofA1)-D | V | OMe |
336 | 4-(2-氟苯基脲)苯基乙酰基 | L | D | V/P | OH |
337 | 2-MPUPA | L | D | V/P/S | OH |
338 | 2-MPUPA | L | D | V/P/S/T | OH |
339 | 2-MPUPA | V | L | P/D | OH |
340 | 2-MPUPA | v | I | p/d | OH |
341 | 2-MPUPA | L | P | V/D | OH |
342 | 2-MPUPA | P | D | ----- | OH |
343 | 氢 | p | v | d/I | 2-MPUBA |
344 | 氢 | v | d | I | 2-MPUBA |
345 | 2-MPUPA | L | D | V | OH |
化合物# | Z | A1 | A2 | (A3)n | X |
346 | 4-(N-(6-甲基-2-吡啶基)脲)苯基乙酰基 | L | D | V/P | OH |
347 | 4-(N-2-氟苯基脲)苯基乙酰基 | L | D | V/P | OH |
348 | 4-苯基丁酰基 | (N-Me)-L | D | V | NHMe |
349 | 苯基乙酰基 | S | D | V | NHMe |
350 | 苯基乙酰基 | K | D | V | NHMe |
351 | 苯基乙酰基 | L | D | A(R2=Me) | NHMe |
352 | 苯基乙酰基 | L | D | (O-Bn)-S | NHMe |
353 | 2-喹啉羰基 | L | D | (O-Bn)-S | NHMe |
354 | Boc | L | D | T | NHBu |
355 | Boc | L | D | V/P | OH |
356 | 2-喹啉羰基 | L | D | V/P | OH |
357 | 4-(N′-2-吡啶基脲)苯基乙酰基 | L | D | V/P | NH2 |
358 | 2-MPUPA | L | D*THAM | V/P | OTHAM |
359 | 2-MPUPA | L | D*Na | V/P | ONa |
360 | 2-MPUPA | L(I) | Het1 | ----- | ----- |
361 | 2-MPUPA | I | Het1 | ----- | ----- |
362 | 2-MPUPA | L(I) | Het2 | ----- | ----- |
363 | 2-MPUPA | L(I) | Het3 | ----- | ----- |
364 | 2-MPUPA | L(I) | Het4 | ----- | ----- |
365 | 2-MPUPA | L(I) | Het5 | ----- | ----- |
366 | 芴基甲氧基羰基 | L | D | V | OH |
367 | 3-甲氧基苯基乙酰基 | L | D | V | OH |
368 | 3-(3-甲基吲哚基)丙酰基 | L | D | V | OH |
369 | 2-苯基-3-甲基-吡唑-4-基羰基 | L | D | V | OH |
370 | 6-甲基苯并嘧啶酮-2-基羰基 | L | D | V | OH |
化合物# | Z | A1 | A2 | (A3)n | X |
371 | 4-氧代-4,5,6,7-四氢苯并[b]呋喃-3-基羰基 | L | D | V | OH |
372 | 3-(5-(苯基乙炔基))吡啶羰基 | L | D | V | OH |
373 | 3-(2-苯硫基)-吡啶羰基 | L | D | V | OH |
374 | 4-丙基苯甲酰基 | L | D | V | OH |
375 | 4-(2-(3-吡啶基))噻唑羰基 | L | D | V | OH |
376 | 4-(2-(4-吡啶基))噻唑羰基 | L | D | V | OH |
377 | 5-(2-(3-吡啶基))噻吩磺酰基 | L | D | V | OH |
378 | 5-(2-(1-吡咯基))吡啶羰基 | L | D | V | OH |
379 | N,N-(4-三氟甲基吡啶-2-基)甲基肼基羰基 | L | D | V | OH |
380 | 2-喹喔啉基氨基羰基 | L | D | V | OH |
381 | N-(4-三氟甲基吡啶-2-基)哌嗪基羰基 | L | D | V | OH |
382 | 5-(2-(2-三氟甲基)苯基磺酰基)-1,2,3,4-四氢噻吩磺酰基 | L | D | V | OH |
383 | 1-(4-氯苯基甲基)吡咯烷-2-酮-4-基羰基 | L | D | V | OH |
384 | 1-(2-呋喃基甲基)吡咯烷-2-酮-4-基羰基 | L | D | V | OH |
385 | 2-(1-吡咯基)苯甲酰基 | L | D | V | OH |
386 | 6-氯苯并二氢吡喃-3-基羰基 | L | D | V | OH |
387 | 2,3-二氢苯并呋喃-5-基羰基 | L | D | V | OH |
388 | 4,6-二甲基吡唑并[1,5-c]三嗪-3-基羰基 | L | D | V | OH |
389 | 3,4-苯并环己酰基 | L | D | V | OH |
390 | 降冰片基乙酰基 | L | D | V | OH |
391 | 1,2,3,4-四氢-9-吖啶基羰基 | L | D | V | OH |
392 | 5,6,7,8-四氢萘基氨基羰基 | L | D | V | OH |
化合物# | Z | A1 | A2 | (A3)n | X |
393 | 3-(2-(4-甲硫基苯氧基))-吡啶羰基 | L | D | V | OH |
394 | 2-(6-甲氧基萘-2-基)丙酰基 | L | D | V | OH |
395 | (2-萘氧基)乙酰基 | L | D | V | OH |
396 | 3-奎宁环基氨基羰基 | L | D | V | OH |
397 | 2-(1,2,3,4-四氢异喹啉)羰基 | L | D | V | OH |
398 | 金刚烷-2-基羰基 | L | D | V | OH |
399 | (2-吡啶基)乙酰基 | L | D | V | OH |
400 | 6-甲基环己烯-2-基羰基 | L | D | V | OH |
401 | (3-喹啉基)乙酰基 | L | D | V | OH |
402 | 4-(2-丁基)苯基氨基羰基 | L | D | V | OH |
403 | 1,4-二氢-1-乙基-7-甲基-4-氧代-1,8-二氮杂萘-3-基羰基 | L | D | V | OH |
404 | (2-噻吩基)乙酰基 | L | D | V | OH |
405 | 4-(2-丙基)苯甲酰基 | L | D | V | OH |
406 | 3,4-亚甲基二氧基苯甲酰基 | L | D | V | OH |
407 | 2-(5-(2-吡啶基)噻吩羰基 | L | D | V | OH |
408 | N-亚氨基二苄基羰基 | L | D | V | OH |
409 | 2-MPUPA | P | D | I | NHMe |
410 | 2-MPUPA | P | D | I | OMe |
411 | 2-MPUPA | P | D | I | OH |
412 | 2-MPUPA | -CH2CH2-(NofR1) | D | I | OH |
413 | 2-MPUPA | P | E | ----- | NMe |
414 | 2-MPUPA | P | E | I | NMe |
415 | 2-MPUPA | P | E | I | OH |
416 | 2-MPUPA | P | E | ----- | OH |
化合物# | IC50 | 化合物# | IC50 | 化合物# | IC50 | 化合物# | IC50 |
1 | A | 30 | C | 59 | B | 88 | C |
2 | A | 31 | C | 60 | C | 89 | C |
3 | A | 32 | C | 61 | B | 90 | C |
4 | A | 33 | C | 62 | C | 91 | C |
5 | C | 34 | B | 63 | C | 92 | C |
6 | C | 35 | B | 64 | C | 93 | C |
7 | C | 36 | C | 65 | C | 94 | C |
8 | C | 37 | C | 66 | C | 95 | C |
9 | C | 38 | C | 67 | C | 96 | C |
10 | C | 39 | C | 68 | C | 97 | C |
11 | C | 40 | C | 69 | C | 98 | C |
12 | C | 41 | B | 70 | C | 99 | C |
13 | B | 42 | B | 71 | C | 100 | C |
14 | C | 43 | B | 72 | C | 101 | C |
15 | C | 44 | B | 73 | C | 102 | C |
16 | C | 45 | C | 74 | C | 103 | C |
17 | C | 46 | C | 75 | C | 104 | C |
18 | B | 47 | C | 76 | C | 105 | C |
19 | C | 48 | C | 77 | C | 106 | C |
20 | C | 49 | C | 78 | C | 107 | C |
21 | C | 50 | C | 79 | C | 108 | C |
22 | C | 51 | C | 80 | C | 109 | C |
23 | C | 52 | C | 81 | C | 110 | C |
24 | C | 53 | C | 82 | C | 111 | C |
25 | C | 54 | C | 83 | C | 112 | C |
26 | C | 55 | C | 84 | C | 113 | C |
27 | C | 56 | B | 85 | C | 114 | C |
28 | C | 57 | B | 86 | C | 115 | C |
29 | C | 58 | B | 87 | C | 116 | C |
化合物# | IC50 | 化合物# | IC50 | 化合物# | IC50 | 化合物# | IC50 |
117 | C | 146 | A | 175 | B | 204 | B |
118 | C | 147 | A | 176 | C | 205 | B |
119 | C | 148 | A | 177 | C | 206 | A |
120 | C | 149 | C | 178 | C | 207 | B |
121 | C | 150 | C | 179 | C | 208 | A |
122 | C | 151 | C | 180 | B | 209 | B |
123 | C | 152 | C | 181 | C | 210 | B |
124 | C | 153 | C | 182 | C | 211 | B |
125 | C | 154 | C | 183 | C | 212 | B |
126 | C | 155 | C | 184 | C | 213 | B |
127 | C | 156 | B | 185 | C | 214 | B |
128 | C | 157 | B | 186 | C | 215 | B |
129 | C | 158 | C | 187 | C | 216 | B |
130 | C | 159 | C | 188 | C | 217 | B |
131 | C | 160 | C | 189 | C | 218 | B |
132 | C | 161 | C | 190 | C | 219 | A |
133 | C | 162 | C | 191 | C | 220 | A |
134 | C | 163 | C | 192 | B | 221 | A |
135 | C | 164 | B | 193 | C | 222 | A |
136 | C | 165 | C | 194 | nd | 223 | A |
137 | C | 166 | C | 195 | C | 224 | A |
138 | C | 167 | C | 196 | C | 225 | A |
139 | C | 168 | B | 197 | B | 226 | A |
140 | C | 169 | C | 198 | C | 227 | A |
141 | C | 170 | C | 199 | B | 228 | A |
142 | C | 171 | C | 200 | B | 229 | A |
143 | C | 172 | C | 201 | B | 230 | A |
144 | A | 173 | C | 202 | B | 231 | A |
145 | A | 174 | B | 203 | A | 232 | A |
化合物# | IC50 | 化合物# | IC50 | 化合物# | IC50 | 化合物# | IC50 |
233 | A | 262 | A | 291 | A | 320 | B |
234 | A | 263 | A | 292 | A | 321 | B |
235 | A | 264 | A | 293 | A | 322 | A |
236 | A | 265 | A | 294 | A | 323 | B |
237 | A | 266 | A | 295 | A | 324 | B |
238 | A | 267 | A | 296 | A | 325 | B |
239 | A | 268 | A | 297 | A | 326 | A |
240 | A | 269 | A | 298 | A | 327 | A |
241 | A | 270 | A | 299 | A | 328 | A |
242 | A | 271 | A | 300 | A | 329 | A |
243 | A | 272 | A | 301 | A | 330 | C |
244 | A | 273 | A | 302 | A | 331 | C |
245 | A | 274 | A | 303 | A | 332 | C |
246 | A | 275 | A | 304 | A | 333 | C |
247 | A | 276 | A | 305 | A | 334 | C |
248 | A | 277 | A | 306 | A | 335 | C |
249 | A | 278 | A | 307 | A | 336 | A |
250 | A | 279 | A | 308 | A | 337 | A |
251 | A | 280 | A | 309 | A | 338 | A |
252 | A | 281 | A | 310 | A | 339 | C |
253 | A | 282 | A | 311 | A | 340 | C |
254 | A | 283 | A | 312 | A | 341 | C |
255 | A | 284 | A | 313 | A | 342 | C |
256 | A | 285 | A | 314 | A | 343 | C |
257 | A | 286 | A | 315 | A | 344 | C |
258 | A | 287 | A | 316 | A | 345 | A |
259 | A | 288 | A | 317 | A | 346 | A |
260 | A | 289 | A | 318 | A | 347 | A |
261 | A | 290 | A | 319 | B | 348 | C |
化合物# | IC50 | 化合物# | IC50 | 化合物# | IC50 | 化合物# | IC50 |
349 | C | 366 | C | 383 | nd | 401 | nd |
350 | C | 367 | C | 384 | nd | 402 | nd |
351 | C | 368 | C | 385 | nd | 403 | C |
352 | C | 369 | C | 386 | C | 404 | C |
353 | C | 370 | C | 387 | C | 405 | C |
354 | C | 371 | B | 388 | nd | 406 | C |
355 | nd | 372 | C | 389 | nd | 407 | C |
356 | nd | 373 | C | 390 | C | 408 | C |
357 | nd | 374 | C | 391 | C | 409 | B |
358 | A | 375 | B | 392 | nd | 410 | B |
359 | A | 376 | C | 393 | C | 411 | A |
360 | C | 377 | nd | 394 | C | 412 | B |
361 | C | 378 | nd | 395 | C | 413 | B |
362 | C | 379 | nd | 396 | nd | 414 | B |
363 | C | 380 | C | 398 | C | 415 | B |
364 | B | 381 | nd | 399 | nd | 416 | B |
365 | B | 382 | nd | 400 | nd |
Claims (35)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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US08/498,237 | 1995-07-11 | ||
US08/498,237 US6248713B1 (en) | 1995-07-11 | 1995-07-11 | Cell adhesion inhibitors |
Publications (2)
Publication Number | Publication Date |
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CN1193325A CN1193325A (zh) | 1998-09-16 |
CN1195778C true CN1195778C (zh) | 2005-04-06 |
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Application Number | Title | Priority Date | Filing Date |
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CNB961963808A Expired - Fee Related CN1195778C (zh) | 1995-07-11 | 1996-07-11 | 细胞粘附抑制剂 |
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US (2) | US6248713B1 (zh) |
EP (1) | EP0842196B1 (zh) |
JP (2) | JPH11511124A (zh) |
KR (1) | KR100531586B1 (zh) |
CN (1) | CN1195778C (zh) |
AU (1) | AU716276B2 (zh) |
BG (1) | BG63876B1 (zh) |
BR (1) | BR9609782A (zh) |
CA (1) | CA2226868A1 (zh) |
CZ (1) | CZ299054B6 (zh) |
DE (1) | DE69637328T2 (zh) |
EA (2) | EA001594B1 (zh) |
EE (2) | EE200200384A (zh) |
FI (1) | FI980033A (zh) |
HK (1) | HK1010888A1 (zh) |
HU (1) | HUP9802202A3 (zh) |
IL (1) | IL122783A (zh) |
IS (1) | IS4648A (zh) |
MX (1) | MX9800348A (zh) |
NO (1) | NO980097L (zh) |
NZ (1) | NZ312950A (zh) |
PL (1) | PL188446B1 (zh) |
RO (1) | RO121032B1 (zh) |
SK (1) | SK3798A3 (zh) |
TR (1) | TR199800028T1 (zh) |
TW (1) | TW570927B (zh) |
UA (1) | UA71888C2 (zh) |
WO (1) | WO1997003094A1 (zh) |
Families Citing this family (131)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6248713B1 (en) * | 1995-07-11 | 2001-06-19 | Biogen, Inc. | Cell adhesion inhibitors |
US6037324A (en) * | 1996-01-04 | 2000-03-14 | Leukosite, Inc. | Inhibitors of MAdCAM-1-mediated interactions and methods of use therefor |
ES2285735T3 (es) | 1996-07-25 | 2007-11-16 | Biogen Idec Inc | Modelo molecular para inhibidores de vla-4. |
US6686350B1 (en) | 1996-07-25 | 2004-02-03 | Biogen, Inc. | Cell adhesion inhibitors |
US6221888B1 (en) | 1997-05-29 | 2001-04-24 | Merck & Co., Inc. | Sulfonamides as cell adhesion inhibitors |
US6903075B1 (en) | 1997-05-29 | 2005-06-07 | Merck & Co., Inc. | Heterocyclic amide compounds as cell adhesion inhibitors |
US6291511B1 (en) | 1997-05-29 | 2001-09-18 | Merck & Co., Inc. | Biarylalkanoic acids as cell adhesion inhibitors |
ATE318841T1 (de) * | 1997-05-29 | 2006-03-15 | Merck & Co Inc | Biarylalkansäuren in der verwendung als zelladhäsionsinhibitoren |
DE69820614T2 (de) * | 1997-05-30 | 2004-09-30 | Celltech Therapeutics Ltd., Slough | Entzündungshemmende tyrosin-derivate |
US6362341B1 (en) | 1997-07-31 | 2002-03-26 | Athena Neurosciences, Inc. | Benzyl compounds which inhibit leukocyte adhesion mediated by VLA-4 |
US6423688B1 (en) | 1997-07-31 | 2002-07-23 | Athena Neurosciences, Inc. | Dipeptide and related compounds which inhibit leukocyte adhesion mediated by VLA-4 |
US6559127B1 (en) | 1997-07-31 | 2003-05-06 | Athena Neurosciences, Inc. | Compounds which inhibit leukocyte adhesion mediated by VLA-4 |
US7030114B1 (en) | 1997-07-31 | 2006-04-18 | Elan Pharmaceuticals, Inc. | Compounds which inhibit leukocyte adhesion mediated by VLA-4 |
US6291453B1 (en) | 1997-07-31 | 2001-09-18 | Athena Neurosciences, Inc. | 4-amino-phenylalanine type compounds which inhibit leukocyte adhesion mediated by VLA-4 |
AR016133A1 (es) * | 1997-07-31 | 2001-06-20 | Wyeth Corp | Compuesto de carbamiloxi que inhiben la adhesion de leucocitos mediada por vla-4, compuestos que son prodrogas de dichos compuestos, composicionfarmaceutica, metodo para fijar vla-4 a una muestra biologica, metodo para el tratamiento de una condicion inflamatoria |
US6489300B1 (en) | 1997-07-31 | 2002-12-03 | Eugene D. Thorsett | Carbamyloxy compounds which inhibit leukocyte adhesion mediated by VLA-4 |
US6939855B2 (en) * | 1997-07-31 | 2005-09-06 | Elan Pharmaceuticals, Inc. | Anti-inflammatory compositions and method |
US6583139B1 (en) | 1997-07-31 | 2003-06-24 | Eugene D. Thorsett | Compounds which inhibit leukocyte adhesion mediated by VLA-4 |
US6492421B1 (en) | 1997-07-31 | 2002-12-10 | Athena Neurosciences, Inc. | Substituted phenylalanine type compounds which inhibit leukocyte adhesion mediated by VLA-4 |
DE19741235A1 (de) | 1997-09-18 | 1999-03-25 | Hoechst Marion Roussel De Gmbh | Neue Imidazolidinderivate, ihre Herstellung, ihre Verwendung und sie enthaltende pharmazeutische Präparate |
DE19741873A1 (de) * | 1997-09-23 | 1999-03-25 | Hoechst Marion Roussel De Gmbh | Neue 5-Ring-Heterocyclen, ihre Herstellung, ihre Verwendung und sie enthaltende pharmazeutische Präparate |
US6069163A (en) * | 1997-10-21 | 2000-05-30 | Merck & Co., Inc. | Azapeptide acids as cell adhesion inhibitors |
DK1027328T3 (da) * | 1997-10-31 | 2006-11-13 | Aventis Pharma Ltd | Substituerede anilider |
GB9723789D0 (en) | 1997-11-12 | 1998-01-07 | Zeneca Ltd | Chemical compounds |
AU1415099A (en) * | 1997-11-18 | 1999-06-07 | Merck & Co., Inc. | 4-substituted-4-piperidine carboxamide derivatives |
US6020347A (en) * | 1997-11-18 | 2000-02-01 | Merck & Co., Inc. | 4-substituted-4-piperidine carboxamide derivatives |
DE19751251A1 (de) | 1997-11-19 | 1999-05-20 | Hoechst Marion Roussel De Gmbh | Substituierte Imidazolidinderivate, ihre Herstellung, ihre Verwendung und sie enthaltende pharmezeutische Präparate |
US6191171B1 (en) | 1997-11-20 | 2001-02-20 | Merck & Co., Inc. | Para-aminomethylaryl carboxamide derivatives |
US6090841A (en) * | 1997-11-21 | 2000-07-18 | Merck & Co., Inc. | Substituted pyrrole derivatives as cell adhesion inhibitors |
US6645939B1 (en) | 1997-11-24 | 2003-11-11 | Merck & Co., Inc. | Substituted β-alanine derivatives as cell adhesion inhibitors |
AU751950B2 (en) * | 1997-11-24 | 2002-09-05 | Merck & Co., Inc. | Substituted beta-alanine derivatives as cell adhesion inhibitors |
US6407065B1 (en) | 1998-01-23 | 2002-06-18 | Novartis Ag | VLA-4 antagonists |
US6329372B1 (en) | 1998-01-27 | 2001-12-11 | Celltech Therapeutics Limited | Phenylalanine derivatives |
GB9805655D0 (en) | 1998-03-16 | 1998-05-13 | Celltech Therapeutics Ltd | Chemical compounds |
US6521626B1 (en) | 1998-03-24 | 2003-02-18 | Celltech R&D Limited | Thiocarboxamide derivatives |
AU3716499A (en) * | 1998-04-21 | 1999-11-08 | Aventis Pharma Limited | Substituted diamines and their use as cell adhesion inhibitors |
DE19821483A1 (de) | 1998-05-14 | 1999-11-18 | Hoechst Marion Roussel De Gmbh | Imidazolidinderivate, ihre Herstellung, ihre Verwendung und sie enthaltende pharmazeutische Präparate |
GB9811159D0 (en) | 1998-05-22 | 1998-07-22 | Celltech Therapeutics Ltd | Chemical compounds |
DK1082302T3 (da) | 1998-05-28 | 2004-04-26 | Biogen Inc | En VLA-4-inhibitor: oMePUPA-V |
GB9811969D0 (en) | 1998-06-03 | 1998-07-29 | Celltech Therapeutics Ltd | Chemical compounds |
GB9814414D0 (en) | 1998-07-03 | 1998-09-02 | Celltech Therapeutics Ltd | Chemical compounds |
WO2000002903A1 (en) * | 1998-07-10 | 2000-01-20 | Cytel Corporation | Cs-1 peptidomimetics, compositions and methods of using the same |
GB9916374D0 (en) | 1998-07-23 | 1999-09-15 | Zeneca Ltd | Chemical compounds |
GB9821061D0 (en) | 1998-09-28 | 1998-11-18 | Celltech Therapeutics Ltd | Chemical compounds |
GB9821222D0 (en) | 1998-09-30 | 1998-11-25 | Celltech Therapeutics Ltd | Chemical compounds |
GB9825652D0 (en) | 1998-11-23 | 1999-01-13 | Celltech Therapeutics Ltd | Chemical compounds |
GB9826174D0 (en) | 1998-11-30 | 1999-01-20 | Celltech Therapeutics Ltd | Chemical compounds |
GB9828074D0 (en) | 1998-12-18 | 1999-02-17 | Glaxo Group Ltd | Therapeutically useful compounds |
AU1881900A (en) * | 1998-12-23 | 2000-07-31 | Aventis Pharma Limited | Dihydro-benzo(1,4)oxazines and tetrahydroquinoxalines |
US6407066B1 (en) | 1999-01-26 | 2002-06-18 | Elan Pharmaceuticals, Inc. | Pyroglutamic acid derivatives and related compounds which inhibit leukocyte adhesion mediated by VLA-4 |
DE19922462A1 (de) | 1999-05-17 | 2000-11-23 | Aventis Pharma Gmbh | Spiro-imidazolidinderivate, ihre Herstellung ihre Verwendung und sie enthaltende pharmazeutische Präparate |
US6518283B1 (en) | 1999-05-28 | 2003-02-11 | Celltech R&D Limited | Squaric acid derivatives |
US6756378B2 (en) | 1999-06-30 | 2004-06-29 | Pharmacopeia Drug Discovery, Inc. | VLA-4 inhibitor compounds |
CN1391473A (zh) * | 1999-06-30 | 2003-01-15 | 第一制药株式会社 | Vla-4抑制剂化合物 |
ES2270868T3 (es) | 1999-08-13 | 2007-04-16 | Biogen Idec Ma Inc. | Inhibidores de la adhesion celular. |
US6534513B1 (en) | 1999-09-29 | 2003-03-18 | Celltech R&D Limited | Phenylalkanoic acid derivatives |
DK1242118T3 (da) | 1999-12-16 | 2010-01-11 | Biogen Idec Inc | Fremgangsmåder til behandling af iskæmisk eller hæmorrhagisk beskadigelse af centralnervesystemet under anvendelse af anti-alfa4-integrin-antagonister |
US6455539B2 (en) | 1999-12-23 | 2002-09-24 | Celltech R&D Limited | Squaric acid derivates |
PL357109A1 (en) | 1999-12-28 | 2004-07-12 | Pfizer Products Inc. | Non-peptidyl inhibitors of vla-4 dependent cell binding useful in treating inflammatory, autoimmune, and respiratory diseases |
AU2001248553A1 (en) | 2000-04-17 | 2001-10-30 | Celltech R And D Limited | Enamine derivatives as cell adhesion molecules |
US6545013B2 (en) | 2000-05-30 | 2003-04-08 | Celltech R&D Limited | 2,7-naphthyridine derivatives |
US6403608B1 (en) | 2000-05-30 | 2002-06-11 | Celltech R&D, Ltd. | 3-Substituted isoquinolin-1-yl derivatives |
AU2001267753A1 (en) | 2000-07-07 | 2002-01-21 | Celltech R And D Limited | Squaric acid derivatives containing a bicyclic heteroaromatic ring as integrin antagonists |
WO2002010136A1 (en) | 2000-08-02 | 2002-02-07 | Celltech R & D Limited | 3-substituted isoquinolin-1-yl derivatives |
AU2002248910A1 (en) * | 2000-11-17 | 2002-05-27 | Idenix (Cayman) Limited | Methods for inhibiting the transmission of HIV using topically applied substituted 6-benzyl-4-oxopyrmidines |
US6875743B1 (en) | 2000-11-28 | 2005-04-05 | Biogen, Inc. | Cell adhesion inhibitors |
RU2290403C2 (ru) | 2000-12-28 | 2006-12-27 | Дайити Фармасьютикал Ко., Лтд. | Ингибиторы vla-4 |
DE10111877A1 (de) | 2001-03-10 | 2002-09-12 | Aventis Pharma Gmbh | Neue Imidazolidinderivate, ihre Herstellung, ihre Verwendung und sie enthaltende pharmazeutische Präparate |
GB2377933A (en) | 2001-07-06 | 2003-01-29 | Bayer Ag | Succinic acid derivatives useful as integrin antagonists |
DE10137595A1 (de) | 2001-08-01 | 2003-02-13 | Aventis Pharma Gmbh | Neue Imidazolidinderivate, ihre Herstellung und ihre Verwendung |
DE60232250D1 (de) * | 2001-08-20 | 2009-06-18 | Honeywell Int Inc | Bogenförmige federelemente für mikro-elektromechanischen beschleunigungssensor |
AR038136A1 (es) | 2002-01-24 | 2004-12-29 | Merck Frosst Canada Inc | Cicloalcanindoles con sustitucion con fluor composiciones que contienen estos compuestos y metodos de tratamiento |
US7247725B2 (en) | 2002-10-30 | 2007-07-24 | Merck & Co., Inc. | Gamma-aminoamide modulators of chemokine receptor activity |
CN1826336B (zh) | 2003-07-24 | 2010-06-02 | 第一制药株式会社 | 环己烷羧酸类 |
CN1301426C (zh) * | 2003-08-19 | 2007-02-21 | 友达光电股份有限公司 | 窄边框设计的液晶显示面板及其制作方法 |
JPWO2005066124A1 (ja) * | 2003-12-26 | 2007-12-20 | 第一三共株式会社 | ピロリジン誘導体の製造法 |
WO2005122379A2 (en) * | 2004-05-27 | 2005-12-22 | The Regents Of The University Of California | Alpha-4 beta-1 integrin ligands for imaging and therapy |
US20060063828A1 (en) * | 2004-06-28 | 2006-03-23 | Weingarten M D | 1,2-Bis-(substituted-phenyl)-2-propen-1-ones and pharmaceutical compositions thereof |
US7196112B2 (en) | 2004-07-16 | 2007-03-27 | Biogen Idec Ma Inc. | Cell adhesion inhibitors |
US7140250B2 (en) * | 2005-02-18 | 2006-11-28 | Honeywell International Inc. | MEMS teeter-totter accelerometer having reduced non-linearty |
JP5107724B2 (ja) | 2005-12-13 | 2012-12-26 | 第一三共株式会社 | Vla−4阻害薬 |
WO2008103378A2 (en) | 2007-02-20 | 2008-08-28 | Merrimack Pharmaceuticals, Inc. | Methods of treating multiple sclerosis by administration of alpha-fetoprotein in combination with an integrin antagonist |
CA2707785C (en) | 2007-12-14 | 2015-11-03 | Pulmagen Therapeutics (Asthma) Limited | Indoles and their therapeutic use |
PL2288715T3 (pl) | 2008-04-11 | 2015-03-31 | Merrimack Pharmaceuticals Inc | Łączniki będące albuminą surowicy ludzkiej i ich koniugaty |
CA2737483A1 (en) | 2008-09-22 | 2010-03-25 | Merck Frosst Canada Ltd. | Indole derivatives as crth2 receptor antagonists |
EP2393814A1 (en) | 2009-02-09 | 2011-12-14 | SuperGen, Inc. | Pyrrolopyrimidinyl axl kinase inhibitors |
CN102395586A (zh) | 2009-02-17 | 2012-03-28 | 奇斯药制品公司 | 作为p38map激酶抑制剂的三唑并吡啶衍生物 |
GB0902648D0 (en) | 2009-02-17 | 2009-04-01 | Argenta Discovery Ltd | Pharmaceutical compounds and compositions |
NZ594767A (en) | 2009-02-24 | 2013-05-31 | Merck Canada Inc | Indole derivatives as crth2 receptor antagonists |
CN102822175A (zh) * | 2009-12-18 | 2012-12-12 | 埃迪尼克斯医药公司 | 5,5-稠合的亚芳基或亚杂芳基丙型肝炎病毒抑制剂 |
GB201009731D0 (en) | 2010-06-10 | 2010-07-21 | Pulmagen Therapeutics Inflamma | Kinase inhibitors |
WO2012031228A2 (en) | 2010-09-02 | 2012-03-08 | The Regents Of The University Of California | Llp2a-bisphosphonate conjugates for osteoporosis treatment |
US8927559B2 (en) | 2010-10-11 | 2015-01-06 | Merck Sharp & Dohme Corp. | Quinazolinone-type compounds as CRTH2 antagonists |
WO2012087861A1 (en) | 2010-12-23 | 2012-06-28 | Merck Sharp & Dohme Corp. | Quinoxalines and aza-quinoxalines as crth2 receptor modulators |
RU2612217C2 (ru) | 2011-05-04 | 2017-03-03 | Мерк Шарп И Доум Корп. | Аминопиридинсодержащие ингибиторы тирозинкиназы селезенки (syk) |
US20140128367A1 (en) | 2011-06-17 | 2014-05-08 | Merck Sharp & Dohme Corp. | Cycloalkyl-fused tetrahydroquinolines as crth2 receptor modulators |
EP2763975B1 (en) | 2011-10-05 | 2016-04-06 | Merck Sharp & Dohme Corp. | 3-pyridyl carboxamide-containing spleen tyrosine kinase (syk) inhibitors |
EP2788345B1 (en) | 2011-12-09 | 2020-06-10 | Chiesi Farmaceutici S.p.A. | Derivatives of 4-hydroxy-1,2,3,4-tetrahydronaphtalen-1-yl urea and their use in the treatment of, inter alia, diseases of the respiratory tract |
RU2623734C9 (ru) | 2011-12-09 | 2017-09-18 | КЬЕЗИ ФАРМАЧЕУТИЧИ С.п.А. | Ингибиторы киназы |
ES2612259T3 (es) | 2011-12-09 | 2017-05-16 | Chiesi Farmaceutici S.P.A. | Inhibidores de cinasa |
US9181242B2 (en) | 2013-06-06 | 2015-11-10 | Chiesi Farmaceutici S.P.A. | Kinase inhibitors |
CN104817625A (zh) * | 2014-01-30 | 2015-08-05 | 陈光健 | 寡肽cd03及其制备方法和应用 |
CN104817615A (zh) * | 2014-01-30 | 2015-08-05 | 陈光健 | 寡肽cd05及其制备方法和应用 |
CN104817613A (zh) * | 2014-01-30 | 2015-08-05 | 陈光健 | 寡肽cd06及其制备方法和应用 |
CN104817622A (zh) * | 2014-01-30 | 2015-08-05 | 陈光健 | 寡肽cd04及其制备方法和应用 |
CN105294830A (zh) * | 2014-06-18 | 2016-02-03 | 陈光健 | 一种二肽分子及其制备方法和应用 |
AU2016338410B2 (en) | 2015-10-14 | 2021-07-15 | X-Therma, Inc. | Compositions and methods for reducing ice crystal formation |
TW201720828A (zh) | 2015-11-23 | 2017-06-16 | 赫孚孟拉羅股份公司 | 治療性化合物及組合物以及其使用方法 |
WO2017108736A1 (en) | 2015-12-23 | 2017-06-29 | Chiesi Farmaceutici S.P.A. | N-[3-(3-{4-[[1,2,4]triazolo[4,3-a]pyridin-6-yloxy]-1,2,3,4-tetrahydro-naphthalen-1-yl} -ureido)-phenyl]-methanesulfonamide derivatives and their use as p38 mapk inhibitors |
AR107164A1 (es) | 2015-12-23 | 2018-03-28 | Chiesi Farm Spa | INHIBIDORES DE QUINASA p38 |
EP3394059B1 (en) | 2015-12-23 | 2020-11-25 | Chiesi Farmaceutici S.p.A. | 1-(3-tert-butyl-phenyl)-3-(4-([1,2,4]triazolo[4,3-a]pyridin-6-yloxy)-1,2,3,4-tetrahydro- naphthalen-1-yl)-urea derivatives and their use as p38 mapk inhibitors |
WO2017191098A1 (en) | 2016-05-05 | 2017-11-09 | F. Hoffmann-La Roche Ag | Pyrazole derivatives, compositions and therapeutic use thereof |
EP3510030B1 (en) | 2016-09-06 | 2023-03-22 | F. Hoffmann-La Roche AG | 8-(azetidin-1-yl)-[1,2,4]triazolo[1,5-a]pyridinyl compounds, compositions and methods of use thereof |
EP3538542B1 (en) | 2016-11-11 | 2021-08-04 | Zealand Pharma A/S | Cyclic peptides multimers targeting alpha 4beta 7 integrin |
KR20190100337A (ko) | 2016-12-29 | 2019-08-28 | 에프. 호프만-라 로슈 아게 | 피라졸로피리미딘 화합물 및 이의 사용 방법 |
WO2018140510A1 (en) | 2017-01-25 | 2018-08-02 | Biogen Ma Inc. | Compositions and methods for treatment of stroke and other cns disorders |
EP3596072B1 (en) | 2017-03-14 | 2022-06-22 | F. Hoffmann-La Roche AG | Pyrazolochlorophenyl compounds, compositions and methods of use thereof |
US11286281B2 (en) | 2017-05-10 | 2022-03-29 | Zealand Pharma A/S | Homodetic cyclic peptides targeting alpha-4-beta-7 integrin |
BR112019024322A2 (pt) | 2017-05-22 | 2020-06-16 | F. Hoffmann-La Roche Ag | Compostos e composições terapêuticos e métodos de uso dos mesmos |
CN110678467B (zh) | 2017-05-22 | 2023-06-13 | 豪夫迈·罗氏有限公司 | 治疗化合物和组合物及其使用方法 |
US10364245B2 (en) | 2017-06-07 | 2019-07-30 | Chiesi Farmaceutici S.P.A. | Kinase inhibitors |
JP7339263B2 (ja) | 2018-01-15 | 2023-09-05 | エフ. ホフマン-ラ ロシュ アーゲー | Jak阻害剤としてのピラゾロピリミジン化合物 |
CA3114240C (en) | 2018-10-30 | 2023-09-05 | Gilead Sciences, Inc. | Imidazopyridine derivatives as alpha4beta7 integrin inhibitors |
AU2019373240B2 (en) | 2018-10-30 | 2023-04-20 | Gilead Sciences, Inc. | Quinoline derivatives as alpha4beta7 integrin inhibitors |
US11224600B2 (en) | 2018-10-30 | 2022-01-18 | Gilead Sciences, Inc. | Compounds for inhibition of alpha 4 beta 7 integrin |
CA3115830C (en) | 2018-10-30 | 2023-09-12 | Gilead Sciences, Inc. | Compounds for inhibition of .alpha.4.beta.7 integrin |
JP2022517610A (ja) | 2019-01-10 | 2022-03-09 | シーエスピーシー ゾンチー ファーマシューティカル テクノロジー(シージアチュアン)カンパニー,リミテッド | 複素環化合物塩およびその使用 |
TW202115069A (zh) | 2019-06-18 | 2021-04-16 | 瑞士商赫孚孟拉羅股份公司 | Jak激酶之經四唑取代之吡唑并嘧啶抑制劑及其用途 |
WO2020257145A1 (en) | 2019-06-18 | 2020-12-24 | Genentech, Inc. | Pyrazolopyrimidine sulfone inhibitors of jak kinases and uses thereof |
CN114008050A (zh) | 2019-06-18 | 2022-02-01 | 豪夫迈·罗氏有限公司 | Jak激酶的吡唑并嘧啶芳基醚抑制剂及其用途 |
WO2021030438A1 (en) | 2019-08-14 | 2021-02-18 | Gilead Sciences, Inc. | Compounds for inhibition of alpha 4 beta 7 integrin |
Family Cites Families (24)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
IT1149971B (it) | 1979-06-11 | 1986-12-10 | Syntex Inc | Derivati nonapeptide e decapeptide dell'ormone che rilascia l'ormone luteinizzante |
US4725583A (en) | 1985-01-23 | 1988-02-16 | Abbott Laboratories | Functionalized peptidylaminoalcohols |
US4826815A (en) | 1985-05-17 | 1989-05-02 | Abbott Laboratories | Renin inhibiting compounds |
DK163689A (da) | 1988-04-08 | 1989-10-30 | Sandoz Ag | Peptidderivater |
EP0506748B1 (en) | 1989-12-22 | 1995-12-13 | Commonwealth Scientific And Industrial Research Organisation | Amino acids, peptides or derivatives thereof coupled to fats |
CA2043741C (en) | 1990-06-07 | 2003-04-01 | Kiyofumi Ishikawa | Endothelin antagonistic peptide derivatives |
US5192746A (en) | 1990-07-09 | 1993-03-09 | Tanabe Seiyaku Co., Ltd. | Cyclic cell adhesion modulation compounds |
US5260277A (en) | 1990-09-10 | 1993-11-09 | Tanabe Seiyaku Co., Ltd. | Guanidinyl and related cell adhesion modulation compounds |
WO1992008464A1 (en) | 1990-11-15 | 1992-05-29 | Tanabe Seiyaku Co. Ltd. | Substituted urea and related cell adhesion modulation compounds |
EP0519748B1 (en) | 1991-06-21 | 1998-09-02 | Merck & Co. Inc. | Peptidyl derivatives as inhibitors of interleukin-1B converting enzyme |
WO1993008823A1 (en) | 1991-11-06 | 1993-05-13 | Tanabe Seiyaku Co., Ltd. | Guanidinyl and related cell adhesion modulation compounds |
DE69222433D1 (de) | 1991-11-22 | 1997-10-30 | Yeda Res & Dev | Nicht-peptidische surrogate der arg-gly-asp sequenz und entsprechende pharmazeutische zusammensetzungen |
AU3420693A (en) | 1991-12-24 | 1993-07-28 | Fred Hutchinson Cancer Research Center | Competitive inhibition of high-avidity alpha4-beta1 receptor using tripeptide ldv |
DE4212304A1 (de) | 1992-04-13 | 1993-10-14 | Cassella Ag | Asparaginsäurederivate, ihre Herstellung und Verwendung |
IL102646A (en) | 1992-07-26 | 1996-05-14 | Yeda Res & Dev | Non-peptidic surrogates of the ldv sequence and pharmaceutical compositions comprising them |
SG52262A1 (en) | 1993-01-08 | 1998-09-28 | Tanabe Seiyaku Co | Peptide inhibitors of cell adhesion |
US5314902A (en) * | 1993-01-27 | 1994-05-24 | Monsanto Company | Urea derivatives useful as platelet aggregation inhibitors |
DE4309867A1 (de) | 1993-03-26 | 1994-09-29 | Cassella Ag | Neue Harnstoffderivate, ihre Herstellung und Verwendung |
ES2160626T3 (es) | 1993-04-09 | 2001-11-16 | Toyama Chemical Co Ltd | Inmunomodulador, inhibidor de la adherencia celular, y agente que permite tratar y prevenir enfermedades autoinmunes. |
US5770573A (en) * | 1993-12-06 | 1998-06-23 | Cytel Corporation | CS-1 peptidomimetics, compositions and methods of using the same |
WO1995015973A1 (en) | 1993-12-06 | 1995-06-15 | Cytel Corporation | Cs-1 peptidomimetics, compositions and methods of using the same |
US5434188A (en) | 1994-03-07 | 1995-07-18 | Warner-Lambert Company | 1-ether and 1-thioether-naphthalene-2-carboxamides as inhibitors of cell adhesion and as inhibitors of the activation of HIV |
US6248713B1 (en) * | 1995-07-11 | 2001-06-19 | Biogen, Inc. | Cell adhesion inhibitors |
US6239108B1 (en) * | 1996-07-11 | 2001-05-29 | Biogen, Inc. | Cell adhesion inhibitors |
-
1995
- 1995-07-11 US US08/498,237 patent/US6248713B1/en not_active Expired - Fee Related
-
1996
- 1996-07-11 EE EEP200200384A patent/EE200200384A/xx unknown
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- 1996-07-11 IL IL12278396A patent/IL122783A/xx not_active IP Right Cessation
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- 1996-07-11 EA EA200100103A patent/EA003737B1/ru not_active IP Right Cessation
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- 1996-07-11 DE DE69637328T patent/DE69637328T2/de not_active Expired - Fee Related
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- 1996-07-12 TW TW085108493A patent/TW570927B/zh not_active IP Right Cessation
- 1996-11-07 UA UA98020687A patent/UA71888C2/uk unknown
-
1998
- 1998-01-08 IS IS4648A patent/IS4648A/is unknown
- 1998-01-09 NO NO980097A patent/NO980097L/no unknown
- 1998-01-09 FI FI980033A patent/FI980033A/fi unknown
- 1998-01-12 MX MX9800348A patent/MX9800348A/es not_active IP Right Cessation
- 1998-02-10 BG BG102241A patent/BG63876B1/bg unknown
- 1998-11-20 HK HK98112181A patent/HK1010888A1/xx not_active IP Right Cessation
-
2000
- 2000-01-13 US US09/482,296 patent/US6596687B1/en not_active Expired - Fee Related
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