ZA200106527B - Dipeptide compound and medicinal use thereof. - Google Patents
Dipeptide compound and medicinal use thereof. Download PDFInfo
- Publication number
- ZA200106527B ZA200106527B ZA200106527A ZA200106527A ZA200106527B ZA 200106527 B ZA200106527 B ZA 200106527B ZA 200106527 A ZA200106527 A ZA 200106527A ZA 200106527 A ZA200106527 A ZA 200106527A ZA 200106527 B ZA200106527 B ZA 200106527B
- Authority
- ZA
- South Africa
- Prior art keywords
- group
- amino
- hydroxy
- apns
- dimethyl
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims description 125
- 108010016626 Dipeptides Proteins 0.000 title claims description 35
- -1 polycyclic hydrocarbon Chemical class 0.000 claims description 189
- 125000003118 aryl group Chemical group 0.000 claims description 102
- 125000004432 carbon atom Chemical group C* 0.000 claims description 46
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 44
- 125000000217 alkyl group Chemical group 0.000 claims description 28
- 125000003545 alkoxy group Chemical group 0.000 claims description 21
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 21
- 150000003839 salts Chemical class 0.000 claims description 20
- 125000005843 halogen group Chemical group 0.000 claims description 17
- 125000003277 amino group Chemical group 0.000 claims description 13
- 125000001153 fluoro group Chemical group F* 0.000 claims description 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 8
- 229940124321 AIDS medicine Drugs 0.000 claims description 7
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 7
- 125000005842 heteroatom Chemical group 0.000 claims description 7
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 7
- 125000002950 monocyclic group Chemical group 0.000 claims description 7
- 125000003367 polycyclic group Chemical group 0.000 claims description 6
- 229910052717 sulfur Chemical group 0.000 claims description 6
- 125000004434 sulfur atom Chemical group 0.000 claims description 6
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 5
- 229920006395 saturated elastomer Polymers 0.000 claims description 5
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- 125000005160 aryl oxy alkyl group Chemical group 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 2
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- 229930195733 hydrocarbon Natural products 0.000 claims 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 91
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 59
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- 239000000203 mixture Substances 0.000 description 38
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 34
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 32
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- 238000000034 method Methods 0.000 description 16
- 239000011780 sodium chloride Substances 0.000 description 16
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 15
- 230000000694 effects Effects 0.000 description 14
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- DXYJRSGGMXMKOO-UHFFFAOYSA-N 5,5-dimethyl-1,3-thiazolidine-4-carboxamide Chemical compound CC1(C)SCNC1C(N)=O DXYJRSGGMXMKOO-UHFFFAOYSA-N 0.000 description 11
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- 125000006179 2-methyl benzyl group Chemical group [H]C1=C([H])C(=C(C([H])=C1[H])C([H])([H])*)C([H])([H])[H] 0.000 description 10
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- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
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- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
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- 239000000758 substrate Substances 0.000 description 6
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- 238000004458 analytical method Methods 0.000 description 5
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- 125000001246 bromo group Chemical group Br* 0.000 description 5
- 150000002430 hydrocarbons Chemical group 0.000 description 5
- 150000002431 hydrogen Chemical class 0.000 description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- AIOMGEMZFLRFJE-UHFFFAOYSA-N 1,3-thiazolidine-4-carboxamide Chemical compound NC(=O)C1CSCN1 AIOMGEMZFLRFJE-UHFFFAOYSA-N 0.000 description 4
- WORJRXHJTUTINR-UHFFFAOYSA-N 1,4-dioxane;hydron;chloride Chemical compound Cl.C1COCCO1 WORJRXHJTUTINR-UHFFFAOYSA-N 0.000 description 4
- 241000700605 Viruses Species 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 4
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 4
- 239000002775 capsule Substances 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000007796 conventional method Methods 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- 238000010898 silica gel chromatography Methods 0.000 description 4
- CJAAPVQEZPAQNI-UHFFFAOYSA-N (2-methylphenyl)methanamine Chemical compound CC1=CC=CC=C1CN CJAAPVQEZPAQNI-UHFFFAOYSA-N 0.000 description 3
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- LHVJUPHCLWIPLZ-UHFFFAOYSA-N 3-acetyloxy-2-methylbenzoic acid Chemical compound CC(=O)OC1=CC=CC(C(O)=O)=C1C LHVJUPHCLWIPLZ-UHFFFAOYSA-N 0.000 description 3
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- BIVMCMIZWDWDCC-GWCFXTLKSA-N (2s,3s)-4-(1,3-benzodioxol-5-yl)-2-hydroxy-3-[(2-methylpropan-2-yl)oxycarbonylamino]butanoic acid Chemical compound CC(C)(C)OC(=O)N[C@H]([C@H](O)C(O)=O)CC1=CC=C2OCOC2=C1 BIVMCMIZWDWDCC-GWCFXTLKSA-N 0.000 description 2
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- 125000003541 2-chlorobenzoyl group Chemical group ClC1=C(C(=O)*)C=CC=C1 0.000 description 2
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/04—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D277/06—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no 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
- C07D207/16—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Virology (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Molecular Biology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Tropical Medicine & Parasitology (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- AIDS & HIV (AREA)
- Communicable Diseases (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP37447899 | 1999-12-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200106527B true ZA200106527B (en) | 2002-10-21 |
Family
ID=18503920
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200106527A ZA200106527B (en) | 1999-12-28 | 2001-08-08 | Dipeptide compound and medicinal use thereof. |
Country Status (7)
| Country | Link |
|---|---|
| EP (1) | EP1157997A4 (fr) |
| AU (1) | AU779356B2 (fr) |
| CA (1) | CA2362849A1 (fr) |
| NO (1) | NO20014149L (fr) |
| NZ (1) | NZ514017A (fr) |
| WO (1) | WO2001047948A1 (fr) |
| ZA (1) | ZA200106527B (fr) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2005029470A (ja) * | 2001-06-21 | 2005-02-03 | Japan Energy Electronic Materials Inc | 新規ノルスタチン誘導体 |
| JP2006076882A (ja) * | 2002-09-13 | 2006-03-23 | Sumitomo Pharmaceut Co Ltd | 新規なジペプチド化合物及びその医薬用途 |
| WO2005026114A1 (fr) * | 2003-09-17 | 2005-03-24 | Pfizer Inc. | Inhibiteurs de la protease du vih, compositions les contenant et leurs utilisations pharmaceutiques |
| US12083099B2 (en) | 2020-10-28 | 2024-09-10 | Accencio LLC | Methods of treating symptoms of coronavirus infection with viral protease inhibitors |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3408379B2 (ja) * | 1995-06-30 | 2003-05-19 | 株式会社ジャパンエナジー | 新規なジペプチド化合物又はその薬理的に許容される塩及びその医薬用途 |
| US5932550A (en) * | 1995-06-30 | 1999-08-03 | Japan Energy Corporation | Dipeptide compound or pharmaceutically acceptable salt thereof and medical use thereof |
| JPH11286478A (ja) * | 1998-04-01 | 1999-10-19 | Sankyo Co Ltd | Ａｈｐｂａ誘導体を含むジペプチド化合物 |
-
2000
- 2000-12-28 EP EP00987774A patent/EP1157997A4/fr not_active Withdrawn
- 2000-12-28 WO PCT/JP2000/009361 patent/WO2001047948A1/fr not_active Application Discontinuation
- 2000-12-28 AU AU24041/01A patent/AU779356B2/en not_active Ceased
- 2000-12-28 NZ NZ514017A patent/NZ514017A/en unknown
- 2000-12-28 CA CA002362849A patent/CA2362849A1/fr not_active Abandoned
-
2001
- 2001-08-08 ZA ZA200106527A patent/ZA200106527B/en unknown
- 2001-08-27 NO NO20014149A patent/NO20014149L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| EP1157997A1 (fr) | 2001-11-28 |
| NO20014149L (no) | 2001-10-23 |
| WO2001047948A1 (fr) | 2001-07-05 |
| NZ514017A (en) | 2003-10-31 |
| EP1157997A4 (fr) | 2002-05-08 |
| AU779356B2 (en) | 2005-01-20 |
| NO20014149D0 (no) | 2001-08-27 |
| CA2362849A1 (fr) | 2001-07-05 |
| AU2404101A (en) | 2001-07-09 |
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