CN1203596A - 呋喃-和噻吩硫代甲酰胺衍生物,其制备及其作为hiv-1和hiv-1突变型复制的抑制剂的应用 - Google Patents
呋喃-和噻吩硫代甲酰胺衍生物,其制备及其作为hiv-1和hiv-1突变型复制的抑制剂的应用 Download PDFInfo
- Publication number
- CN1203596A CN1203596A CN96198705A CN96198705A CN1203596A CN 1203596 A CN1203596 A CN 1203596A CN 96198705 A CN96198705 A CN 96198705A CN 96198705 A CN96198705 A CN 96198705A CN 1203596 A CN1203596 A CN 1203596A
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- China
- Prior art keywords
- hiv
- compound
- methyl
- reaction mixture
- treatment
- 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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-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Virology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- AIDS & HIV (AREA)
- Tropical Medicine & Parasitology (AREA)
- Molecular Biology (AREA)
- Engineering & Computer Science (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Abstract
Description
化合物 | EC50(μg/ml)a | CC50(μg/ml)b | ||||||
WT | 100-Ile | 103-Asn | 106-Ala | 138-Lys | 181-Cys | 188-Leu | ||
IA | 0.003 | 0.003 | 0.006 | 0.005 | 0.005 | 0.011 | 0.50 | >100 |
IB | 0.003 | 0.004 | 0.004 | 0.005 | 0.005 | 0.005 | 0.60 | 5.8 |
化合物 | EC50(μg/ml)a | CC50(μg/ml)b | ||||||
WT | 100-Ile | 103-Asn | 106-Ala | 138-Lys | 181-Cys | 188-Leu | ||
1 | 0.0055 | 0.048 | 0.048 | 0.023 | 0.018 | 0.03 | 0.65 | 5.9 |
2 | 0.006 | 0.048 | 0.023 | 0.04 | 0.018 | 0.075 | 0.65 | 9.0 |
3 | 0.0065 | 0.057 | 0.23 | 0.03 | 0.045 | 0.08 | 0.91 | 5.8 |
4 | 0.007 | 0.22 | 0.4 | 0.22 | 0.039 | 0.59 | 0.93 | >100 |
5 | 0.013 | 0.055 | 0.08 | 0.025 | 0.04 | 0.025 | >2 | 10 |
6 | 0.0041 | 0.037 | 0.03 | 0.018 | 0.03 | 0.045 | 1.0 | 4.7 |
7 | 0.0065 | 0.065 | 0.058 | 0.03 | 0.04 | 0.045 | 1.2 | 11 |
8 | 0.0055 | 0.032 | 0.023 | 0.023 | 0.025 | 0.025 | ≥2.0 | 5.1 |
9 | 0.0032 | 0.057 | 0.13 | 0.03 | 0.02 | 0.032 | >2 | 6.0 |
10 | 0.02 | 0.65 | 1.27 | 0.23 | 0.09 | 0.033 | >2 | 6.5 |
11 | 0.029 | 0.13 | 0.17 | 0.1 | 0.13 | 0.045 | >2 | 13 |
12 | 0.007 | 0.035 | 0.035 | 0.08 | 0.035 | 0.07 | ≥2.0 | >100 |
13 | 0.08 | 0.26 | 0.38 | 0.17 | 0.25 | 0.07 | >2 | 11.4 |
14 | 0.067 | 0.16 | 0.12 | 0.1 | 0.24 | 0.087 | >2 | 2.1 |
15 | 0.03 | 0.06 | 0.065 | 0.06 | 0.07 | 0.09 | >2 | 11.4 |
16 | 0.0041 | 0.15 | 0.33 | 0.077 | 0.03 | 0.1 | ≥2.0 | 5.9 |
17 | 0.22 | 0.49 | 0.73 | 0.3 | 0.18 | 0.45 | >2 | 7.0 |
18 | 0.014 | 0.33 | 0.33 | 0.15 | 0.22 | 0.13 | >2 | 8.5 |
19 | 0.17 | 0.85 | ≥2.0 | 0.4 | 0.6 | 0.13 | >2 | 5.2 |
20 | 0.13 | 0.34 | 0.44 | 0.15 | 0.43 | 0.14 | >2 | 5.4 |
21 | 0.008 | 0.3 | 0.61 | 0.23 | 0.11 | 0.17 | >2 | 6.0 |
22 | 0.08 | 0.48 | 0.65 | 0.26 | 0.55 | 0.18 | >2 | 5.8 |
23 | 0.03 | 0.7 | ≥2.0 | 0.22 | 0.73 | 0.27 | >2 | 5.8 |
化合物 | EC50(μg/ml)a | CC50(μg/ml)b | ||||||
WT | 100-Ile | 103-Asn | 106-Ala | 138-Lys | 181-Cys | 188-Leu | ||
24 | 0.13 | 0.48 | 0.6 | 0.5 | 0.5 | 0.33 | >2 | 9.7 |
25 | 0.03 | 0.2 | 0.4 | 0.2 | 0.13 | 0.44 | >2 | 3.3 |
26 | 0.033 | 0.33 | 0.33 | 0.09 | 0.50 | ≥2.0 | >2 | 5.3 |
27 | 0.01 | 0.36 | 0.5 | 0.11 | 0.15 | 0.46 | >2 | 6.0 |
28 | 0.029 | 0.22 | 0.33 | 0.23 | 0.11 | 0.5 | >2 | 4.3 |
29 | 0.14 | 0.5 | 0.43 | 0.5 | 0.05 | 0.55 | >2 | 6.2 |
30 | 0.015 | 1.27 | 1.67 | 0.34 | 0.23 | 0.65 | >2 | >100 |
31 | 0.09 | ≥2.0 | ≥2.0 | 0.6 | 0.93 | 0.73 | >2 | 5.5 |
32 | 0.16 | ≥2.0 | ≥2.0 | ≥2.0 | ≥2.0 | 0.95 | >2 | 4.1 |
33 | 0.063 | 0.95 | 1.0 | 0.65 | 0.62 | 1.07 | >2 | 7.0 |
34 | 0.08 | 0.65 | 0.8 | 0.28 | 0.5 | 1.2 | >2 | 4.8 |
35 | 0.16 | 1.5 | 0.55 | 0.8 | 0.7 | 1.6 | >2 | 5.9 |
36 | 0.18 | 1.23 | 1.2 | 0.85 | 0.85 | 1.6 | >2 | 7.8 |
37 | 0.16 | ≥2.0 | ≥2.0 | 1.3 | 1.25 | 1.73 | >2 | 5.0 |
38 | 0.08 | ≥2.0 | ≥2.0 | 0.7 | ≥2.0 | >2 | >2 | 5.5 |
39 | 0.15 | 1.4 | 0.7 | >2 | 0.5 | ≥2.0 | >2 | 4.1 |
40 | 0.24 | 1.4 | ≥2.0 | >2 | 1.2 | >2 | >2 | 5.8 |
41 | 0.28 | ≥2.0 | ≥2.0 | ≥2.0 | ≥2.0 | ≥2.0 | >2 | >100 |
42 | 0.36 | ≥2.0 | ≥2.0 | ≥2.0 | ≥2.0 | ≥2.0 | >2 | 5.0 |
43 | 0.65 | 1.2 | 1.3 | 4.5 | 1.3 | >2 | >2 | 11 |
44 | 0.0073 | 0.035 | 0.08 | 0.06 | 0.03 | 0.08 | >10 | >100 |
化合物 | EC50(μg/ml)a | CC50(μg/ml)b | ||||||
WT | 100-Ile | 103-Asn | 106-Ala | 138-Lys | 181-Cys | 188-Leu | ||
45 | 0.15 | 0.6 | 0.95 | 0.85 | 0.65 | 0.5 | >10.0 | 87 |
46 | 0.37 | 4.5 | 4.0 | 3.0 | 0.6 | 5.5 | ≥2 | 25 |
47 | 0.23 | ≥10 | ≥10 | ≥10 | ≥10 | ≥10 | ≥10 | >100 |
48 | 0.45 | 6.5 | - | 6.5 | 3.5 | 6.0 | - | 3.8 |
49 | 0.007 | 0.6 | - | 0.6 | 0.6 | 0.2 | - | 5.2 |
50 | 0.15 | 5.0 | - | 1.0 | 1.0 | 1.9 | - | 3.7 |
51 | 0.006 | 0.8 | - | 0.03 | 0.03 | 0.10 | - | 6.7 |
52 | 0.70 | 8.5 | - | 5.5 | 4.0 | ≥10 | - | 6.2 |
53 | 0.03 | 0.85 | - | 0.29 | 0.08 | 0.55 | - | 18 |
54 | 0.6 | >10 | - | 5.0 | >10 | 1.0 | - | 44 |
55 | 0.009 | 0.65 | - | 0.08 | 0.18 | 0.11 | - | 17 |
56 | 0.7 | >10 | - | 6.5 | >10 | ≥10 | - | 52 |
57 | 0.009 | 1.3 | - | 0.2 | 0.08 | 0.50 | - | >100 |
58 | 0.19 | 5.5 | - | 7.0 | 6.0 | 5.0 | - | 6.5 |
59 | 0.09 | 0.65 | - | 0.60 | 0.40 | 0.35 | - | 15 |
60 | 0.23 | 4.5 | - | 1.6 | 1.57 | 3.0 | - | 14 |
61 | 0.01 | 0.2 | - | 0.2 | 0.05 | 0.2 | - | 12 |
62 | 0.4 | 3.5 | - | 5.0 | 5.0 | 5.5 | - | 6.2 |
63 | 0.05 | 4.5 | - | 5.0 | 2.2 | 5.0 | - | 4.3 |
64 | 0.6 | ≥10 | - | 2.0 | 4.0 | 5.0 | - | 33 |
65 | 0.04 | 0.3 | - | 0.26 | 0.09 | 0.25 | - | 19 |
66 | 0.6 | >10 | - | 9.0 | >10 | ≥10 | - | 25 |
化合物 | EC50(μg/ml)a | CC50(μg/ml)b | ||||||
WT | 100-Ile | 103-Asn | 106-Ala | 138-Lys | 181-Cys | 188-Leu | ||
67 | 0.75 | ≥10 | - | ≥10 | 5.5 | >10 | - | 29 |
68 | 0.45 | 5.0 | - | 8.5 | 5.5 | 8.5 | - | >100 |
69 | 0.04 | 0.65 | - | 0.65 | 0.55 | 3.5 | - | 10 |
70 | 0.19 | 2.5 | - | 6.5 | 5.5 | 2.5 | - | 5.2 |
71 | 0.049 | 0.6 | - | 3.0 | 3.0 | 1.6 | - | 4.0 |
72 | 0.03 | 2.3 | - | 0.5 | 0.085 | 1.6 | - | 24 |
73 | 0.017 | 2.9 | - | 0.80 | 0.09 | 0.85 | - | >100 |
74 | 0.015 | 6.0 | - | 0.45 | 0.09 | 3.0 | - | >100 |
75 | 0.009 | 0.9 | - | 0.7 | 0.35 | 0.6 | - | 16 |
76 | 0.035 | 2.7 | - | ≥1 | 0.73 | >1 | - | 5.3 |
77 | 0.045 | ≥1 | - | ≥1 | 0.55 | >1 | - | 3.6 |
78 | 0.045 | 5.0 | - | 2.0 | 1.13 | 3.3 | - | 7.1 |
79 | 0.03 | 0.85 | - | 0.07 | 0.07 | 0.08 | - | 4.1 |
80 | 0.50 | 4.0 | - | 5.0 | 4.0 | 3.0 | - | 8.3 |
81 | 0.04 | 0.7 | - | 0.65 | 0.6 | 4.5 | - | 12 |
82 | 0.03 | 2.0 | - | 1.0 | 0.55 | 0.8 | - | 5.2 |
83 | 0.004 | 0.17 | - | 0.057 | 0.035 | 0.07 | - | 9.7 |
84 | 0.049 | 0.6 | - | 3.0 | 3.0 | 1.6 | - | 4.0 |
85 | 0.5 | 6.0 | - | 7.5 | 5.5 | 5.3 | - | 6.7 |
86 | 0.1 | 5.0 | - | 5.0 | 4.0 | 5.0 | - | 7.4 |
87 | 0.02 | 3.0 | - | 1.0 | 0.55 | 0.53 | - | 15 |
88 | 0.01 | 0.7 | - | 0.6 | 0.3 | 0.27 | - | 5.2 |
89 | 0.09 | 3.0 | - | 4.0 | 1.9 | 4.0 | - | 4.9 |
化合物 | EC50(μg/ml)a | CC50(μg/ml)b | ||||||
WT | 100-Ile | 103-Asn | 106-Ala | 138-Lys | 181-Cys | 188-Leu | ||
90 | 0.19 | 3.5 | - | 6.0 | 0.7 | 5.5 | - | 27 |
91 | 0.45 | 4.5 | - | 8.5 | 5.0 | 7.5 | - | 5.8 |
92 | 0.02 | 0.4 | - | 0.75 | 0.50 | 0.37 | - | 4.3 |
93 | 0.03 | 2.0 | - | 0.10 | 0.08 | 0.7 | - | 9.7 |
94 | 0.01 | 0.75 | - | 0.50 | 0.15 | 0.6 | - | 3.1 |
95 | 0.008 | 0.65 | - | 0.08 | 0.16 | 0.5 | - | 13 |
96 | 0.05 | >1 | - | 0.75 | 0.17 | >1 | - | 9.0 |
97 | 0.009 | 3.5 | - | ≥4 | 2.0 | 3.3 | - | 3.3 |
98 | 0.06 | >1 | - | 0.85 | 0.7 | >1 | - | 7.5 |
99 | 0.10 | >1 | - | >10 | >10 | >10 | - | >100 |
100 | 0.03 | 4.0 | - | 0.8 | 0.4 | 0.65 | - | >100 |
101 | 0.045 | 3.0 | - | 0.2 | 0.33 | 0.55 | - | ≥100 |
102 | 0.03 | 0.85 | - | 0.85 | 0.08 | 0.65 | - | 3.7 |
103 | 0.01 | 0.19 | - | 0.075 | 0.06 | 0.07 | - | 8.5 |
104 | 0.01 | 0.65 | - | 0.4 | 0.2 | 0.37 | - | 11 |
105 | 0.015 | 0.4 | - | 0.2 | 0.085 | 0.07 | - | 6.7 |
106 | 0.007 | 0.5 | - | 0.08 | 0.065 | 0.085 | - | >100 |
107 | 0.04 | 0.6 | - | 0.3 | 0.15 | 0.3 | - | 16 |
108 | 0.007 | 0.27 | - | 0.08 | 0.07 | 0.08 | - | 7.0 |
109 | 0.005 | 0.17 | - | 0.04 | 0.035 | 0.045 | - | 4.3 |
110 | 0.04 | 4.0 | - | 0.2 | 0.1 | 0.5 | - | 25 |
111 | 0.007 | 0.5 | - | 0.085 | 0.077 | 0.3 | - | 12 |
112 | 0.025 | 0.75 | - | 0.35 | 0.5 | 0.8 | - | 10 |
化合物 | EC50(μg/ml)a | CC50(μg/ml)b | ||||||
WT | 100-Ile | 103-Asn | 106-Ala | 138-Lys | 181-Cys | 188-Leu | ||
113 | 0.023 | 0.27 | - | 0.085 | 0.15 | 0.13 | - | 5.4 |
114 | 0.05 | 0.085 | - | 0.13 | 0.075 | 0.075 | - | 5.8 |
115 | 0.29 | 0.65 | - | 0.2 | 0.77 | 0.5 | - | 4.3 |
116 | 0.085 | 1.8 | - | 5.5 | 0.6 | 2.0 | - | ≥100 |
117 | 0.06 | 5.0 | - | 0.75 | 0.35 | 4.0 | - | 18 |
Claims (12)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US08/565,493 | 1995-11-30 | ||
US08/565,493 US5696151A (en) | 1995-11-30 | 1995-11-30 | Compounds useful for the inhibition of the replication of HIV-1 and HIV-1 mutants |
Publications (2)
Publication Number | Publication Date |
---|---|
CN1203596A true CN1203596A (zh) | 1998-12-30 |
CN1098847C CN1098847C (zh) | 2003-01-15 |
Family
ID=24258853
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN96198705A Expired - Lifetime CN1098847C (zh) | 1995-11-30 | 1996-11-15 | 呋喃-和噻吩硫代甲酰胺衍生物,其制备及其作为hiv-1和hiv-1突变型复制的抑制剂的应用 |
Country Status (21)
Country | Link |
---|---|
US (1) | US5696151A (zh) |
EP (1) | EP0874839B1 (zh) |
JP (1) | JP3027771B2 (zh) |
KR (1) | KR100505841B1 (zh) |
CN (1) | CN1098847C (zh) |
AP (1) | AP902A (zh) |
AT (1) | ATE224382T1 (zh) |
AU (1) | AU704086B2 (zh) |
BR (1) | BR9611838A (zh) |
CA (1) | CA2237194C (zh) |
DE (1) | DE69623819T2 (zh) |
DK (1) | DK0874839T3 (zh) |
ES (1) | ES2183986T3 (zh) |
HK (1) | HK1016601A1 (zh) |
HU (1) | HU223660B1 (zh) |
NZ (1) | NZ324118A (zh) |
OA (1) | OA10864A (zh) |
PT (1) | PT874839E (zh) |
TW (1) | TW448169B (zh) |
WO (1) | WO1997019940A1 (zh) |
ZA (1) | ZA969490B (zh) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101987842A (zh) * | 2009-07-31 | 2011-03-23 | 上海开拓者医药发展有限公司 | 一种2-甲基噻吩衍生物的制备方法 |
Families Citing this family (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6143780A (en) * | 1999-09-17 | 2000-11-07 | Uniroyal Chemical Company, Inc. | N-arylmethylthioanilide compounds useful for the inhibition of the replication of HIV |
US6017947A (en) * | 1999-09-17 | 2000-01-25 | Brouwer; Walter Gerhard | Heterocyclic carbodithioperoxyimidic compounds useful for the inhibition of the replication of HIV |
US7064139B2 (en) * | 2001-10-29 | 2006-06-20 | Uniroyal Chemical Company, Inc. | Method for treating retroviral infections |
US6498254B1 (en) * | 2001-10-29 | 2002-12-24 | Uniroyal Chemical Company, Inc. | Antiretroviral compounds and compositions |
DE102008015033A1 (de) | 2008-03-17 | 2009-09-24 | Aicuris Gmbh & Co. Kg | Substituierte (Pyrazolyl-carbonyl)imidazolidinone und ihre Verwendung |
DE102008015032A1 (de) | 2008-03-17 | 2009-09-24 | Aicuris Gmbh & Co. Kg | Substituierte Pyrazolamide und ihre Verwendung |
DE102008062878A1 (de) | 2008-12-17 | 2010-06-24 | Aicuris Gmbh & Co. Kg | Substituierte Furancarboxamide und ihre Verwendung |
DE102008062863A1 (de) | 2008-12-17 | 2010-06-24 | Aicuris Gmbh & Co. Kg | Substituierte (Thiophenyl-carbonyl)imidazolidinone und ihre Verwendung |
JP2017522334A (ja) * | 2014-07-24 | 2017-08-10 | バイエル・クロップサイエンス・アクチェンゲゼルシャフト | 殺真菌性ピラゾール誘導体 |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5268389A (en) * | 1989-10-16 | 1993-12-07 | Uniroyal Chemical Company, Inc. | Thiocarboxylate ester compounds compositions containing the same |
US5968910A (en) * | 1994-11-30 | 1999-10-19 | Jan M. R. Balzarini | Compositions containing two or three inhibitors of different HIV reverse transcriptases |
-
1995
- 1995-11-30 US US08/565,493 patent/US5696151A/en not_active Expired - Lifetime
-
1996
- 1996-11-08 TW TW085113662A patent/TW448169B/zh not_active IP Right Cessation
- 1996-11-12 ZA ZA969490A patent/ZA969490B/xx unknown
- 1996-11-15 PT PT96942010T patent/PT874839E/pt unknown
- 1996-11-15 DE DE69623819T patent/DE69623819T2/de not_active Expired - Lifetime
- 1996-11-15 WO PCT/US1996/018394 patent/WO1997019940A1/en active IP Right Grant
- 1996-11-15 KR KR10-1998-0703958A patent/KR100505841B1/ko active IP Right Grant
- 1996-11-15 CA CA002237194A patent/CA2237194C/en not_active Expired - Lifetime
- 1996-11-15 AT AT96942010T patent/ATE224382T1/de active
- 1996-11-15 HU HU9901990A patent/HU223660B1/hu active IP Right Grant
- 1996-11-15 AP APAP/P/1998/001245A patent/AP902A/en active
- 1996-11-15 DK DK96942010T patent/DK0874839T3/da active
- 1996-11-15 EP EP96942010A patent/EP0874839B1/en not_active Expired - Lifetime
- 1996-11-15 BR BR9611838A patent/BR9611838A/pt active Search and Examination
- 1996-11-15 ES ES96942010T patent/ES2183986T3/es not_active Expired - Lifetime
- 1996-11-15 AU AU11199/97A patent/AU704086B2/en not_active Expired
- 1996-11-15 JP JP9520533A patent/JP3027771B2/ja not_active Expired - Lifetime
- 1996-11-15 CN CN96198705A patent/CN1098847C/zh not_active Expired - Lifetime
- 1996-11-15 NZ NZ324118A patent/NZ324118A/xx not_active IP Right Cessation
-
1998
- 1998-05-29 OA OA9800070A patent/OA10864A/en unknown
-
1999
- 1999-04-21 HK HK99101720A patent/HK1016601A1/xx not_active IP Right Cessation
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101987842A (zh) * | 2009-07-31 | 2011-03-23 | 上海开拓者医药发展有限公司 | 一种2-甲基噻吩衍生物的制备方法 |
Also Published As
Publication number | Publication date |
---|---|
ES2183986T3 (es) | 2003-04-01 |
AU1119997A (en) | 1997-06-19 |
HK1016601A1 (en) | 1999-11-05 |
DE69623819D1 (de) | 2002-10-24 |
PT874839E (pt) | 2003-02-28 |
HUP9901990A3 (en) | 2000-08-28 |
EP0874839A1 (en) | 1998-11-04 |
AU704086B2 (en) | 1999-04-15 |
AP902A (en) | 2000-11-23 |
NZ324118A (en) | 1999-02-25 |
EP0874839B1 (en) | 2002-09-18 |
DK0874839T3 (da) | 2003-01-27 |
KR19990071682A (ko) | 1999-09-27 |
KR100505841B1 (ko) | 2005-12-14 |
JPH11504657A (ja) | 1999-04-27 |
US5696151A (en) | 1997-12-09 |
CN1098847C (zh) | 2003-01-15 |
HUP9901990A2 (en) | 2000-07-28 |
CA2237194C (en) | 2006-06-13 |
AP9801245A0 (en) | 1998-06-30 |
OA10864A (en) | 2003-02-18 |
HU223660B1 (hu) | 2004-11-29 |
JP3027771B2 (ja) | 2000-04-04 |
WO1997019940A1 (en) | 1997-06-05 |
CA2237194A1 (en) | 1997-06-05 |
BR9611838A (pt) | 1999-03-09 |
TW448169B (en) | 2001-08-01 |
ZA969490B (en) | 1997-06-02 |
DE69623819T2 (de) | 2003-05-28 |
ATE224382T1 (de) | 2002-10-15 |
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