SU1678207A3 - Способ получени гетероциклических кетонов - Google Patents
Способ получени гетероциклических кетонов Download PDFInfo
- Publication number
- SU1678207A3 SU1678207A3 SU884355719A SU4355719A SU1678207A3 SU 1678207 A3 SU1678207 A3 SU 1678207A3 SU 884355719 A SU884355719 A SU 884355719A SU 4355719 A SU4355719 A SU 4355719A SU 1678207 A3 SU1678207 A3 SU 1678207A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- solution
- product
- evaporated
- dichloromethane
- tlc
- Prior art date
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- -1 heterocyclic ketones Chemical class 0.000 title claims abstract description 89
- 238000000034 method Methods 0.000 title claims description 20
- 238000002360 preparation method Methods 0.000 title abstract description 5
- 239000002253 acid Substances 0.000 claims abstract description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 5
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 5
- 239000001301 oxygen Substances 0.000 claims abstract description 5
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 5
- 239000011593 sulfur Substances 0.000 claims abstract description 5
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000000068 chlorophenyl group Chemical group 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 239000003112 inhibitor Substances 0.000 abstract description 14
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- 230000000694 effects Effects 0.000 abstract description 4
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- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 230000002401 inhibitory effect Effects 0.000 abstract 1
- 231100000161 signs of toxicity Toxicity 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 126
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 108
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 75
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 74
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 72
- 239000000243 solution Substances 0.000 description 62
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 55
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 46
- 239000000047 product Substances 0.000 description 45
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 42
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 36
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- 239000000203 mixture Substances 0.000 description 34
- 238000001819 mass spectrum Methods 0.000 description 28
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- 239000011541 reaction mixture Substances 0.000 description 27
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- 229910052943 magnesium sulfate Inorganic materials 0.000 description 21
- 235000019341 magnesium sulphate Nutrition 0.000 description 21
- 238000003818 flash chromatography Methods 0.000 description 20
- 229960000583 acetic acid Drugs 0.000 description 19
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- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 18
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 18
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- 125000000623 heterocyclic group Chemical group 0.000 description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
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- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 13
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- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical class [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 11
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 11
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- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 8
- 210000004072 lung Anatomy 0.000 description 8
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 8
- NKLCNNUWBJBICK-UHFFFAOYSA-N dess–martin periodinane Chemical compound C1=CC=C2I(OC(=O)C)(OC(C)=O)(OC(C)=O)OC(=O)C2=C1 NKLCNNUWBJBICK-UHFFFAOYSA-N 0.000 description 7
- 238000010828 elution Methods 0.000 description 7
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- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 6
- 239000005711 Benzoic acid Substances 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
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- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 4
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- LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 3
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- KYJNYMVMZKFIKI-LURJTMIESA-N (2s)-2-methylpyrrolidine-2-carboxamide Chemical compound NC(=O)[C@]1(C)CCCN1 KYJNYMVMZKFIKI-LURJTMIESA-N 0.000 description 2
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- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
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- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000005192 partition Methods 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229960003742 phenol Drugs 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000008259 solid foam Substances 0.000 description 1
- 238000000935 solvent evaporation Methods 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 210000003437 trachea Anatomy 0.000 description 1
- 229960004295 valine Drugs 0.000 description 1
- 238000001429 visible spectrum Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- 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
- C07K5/06—Dipeptides
- C07K5/06008—Dipeptides with the first amino acid being neutral
- C07K5/06017—Dipeptides with the first amino acid being neutral and aliphatic
- C07K5/06034—Dipeptides with the first amino acid being neutral and aliphatic the side chain containing 2 to 4 carbon atoms
- C07K5/06052—Val-amino acid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- 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
- C07K5/06—Dipeptides
- C07K5/06191—Dipeptides containing heteroatoms different from O, S, or N
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Molecular Biology (AREA)
- Biophysics (AREA)
- Genetics & Genomics (AREA)
- Biochemistry (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pulmonology (AREA)
- Rheumatology (AREA)
- Pain & Pain Management (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
- Pyridine Compounds (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB878711050A GB8711050D0 (en) | 1987-05-11 | 1987-05-11 | Selected heterocyclic ketones |
| GB888803206A GB8803206D0 (en) | 1988-02-11 | 1988-02-11 | Selected heterocyclic ketones |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU1678207A3 true SU1678207A3 (ru) | 1991-09-15 |
Family
ID=26292230
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU884355719A SU1678207A3 (ru) | 1987-05-11 | 1988-05-06 | Способ получени гетероциклических кетонов |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US5164371A (enExample) |
| EP (1) | EP0291234B1 (enExample) |
| JP (1) | JPS6445395A (enExample) |
| KR (1) | KR880013926A (enExample) |
| CN (1) | CN1037519A (enExample) |
| AT (1) | ATE103293T1 (enExample) |
| AU (1) | AU605284B2 (enExample) |
| CA (1) | CA1326107C (enExample) |
| DE (1) | DE3888568T2 (enExample) |
| DK (1) | DK260588A (enExample) |
| ES (1) | ES2063034T3 (enExample) |
| FI (1) | FI91072C (enExample) |
| GB (1) | GB8809316D0 (enExample) |
| HU (1) | HU201963B (enExample) |
| IE (1) | IE62524B1 (enExample) |
| IL (1) | IL86236A (enExample) |
| NO (1) | NO176519C (enExample) |
| NZ (1) | NZ224452A (enExample) |
| PT (1) | PT87454B (enExample) |
| SU (1) | SU1678207A3 (enExample) |
| ZA (1) | ZA883006B (enExample) |
| ZW (1) | ZW4988A1 (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2319708C2 (ru) * | 2002-02-05 | 2008-03-20 | ДАЙНИППОН СУМИТОМО ФАРМА Ко., ЛТД. | Гетероциклические соединения с эластазоингибирующей активностью и их производные, а также фармацевтическая композиция и средство на их основе |
| EA012727B1 (ru) * | 2004-09-21 | 2009-12-30 | Бёрингер Ингельхайм Интернациональ Гмбх | Гетероарильные соединения в качестве бетамиметиков для лечения заболеваний дыхательных путей |
Families Citing this family (54)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8910550D0 (en) * | 1989-05-08 | 1989-06-21 | Ici America Inc | Substituted amides |
| GB8910547D0 (en) * | 1989-05-08 | 1989-06-21 | Ici America Inc | Substituted ketones |
| DE69129083T2 (de) * | 1990-05-24 | 1998-07-09 | Zeneca Ltd | Therapeutisches Mittel zur Vorbeugung und Behandlung des Atemnotsyndroms bei Erwachsenen |
| US5162348A (en) * | 1990-05-24 | 1992-11-10 | Imperial Chemical Industries Plc | Treatment of cystic fibrosis |
| IE911698A1 (en) * | 1990-05-24 | 1991-12-04 | Ici Plc | Therapeutic compound |
| ES2067140T3 (es) * | 1990-09-10 | 1995-03-16 | Asahi Chemical Ind | Compuestos fenilester de acido benzoico y composiciones inhibidoras de la elastasa que contienen los mismos. |
| US6159938A (en) * | 1994-11-21 | 2000-12-12 | Cortech, Inc. | Serine protease inhibitors comprising α-keto heterocycles |
| US6001813A (en) * | 1994-11-21 | 1999-12-14 | Cortech Inc. | Val-pro containing α-keto oxadiazoles as serine protease inhibitors |
| US6001814A (en) * | 1994-11-21 | 1999-12-14 | Cortech Inc. | Serine protease inhibitors |
| US20020119985A1 (en) | 1994-11-21 | 2002-08-29 | Albert Gyorkos | Serine protease inhibitors |
| US6100238A (en) * | 1994-11-21 | 2000-08-08 | Cortech Inc. | Indole and tetrahydroisoquinoline containing Alpha-keto oxadiazoles as serine protease inhibitors |
| US5998379A (en) * | 1994-11-21 | 1999-12-07 | Cortech Inc. | Serine protease inhibitors-proline analogs |
| US6001811A (en) * | 1994-11-21 | 1999-12-14 | Cortech Inc. | Serine protease inhibitors--N-substituted derivatives |
| US6015791A (en) * | 1994-11-21 | 2000-01-18 | Cortech Inc. | Serine protease inhibitors-cycloheptane derivatives |
| US6150334A (en) * | 1994-11-21 | 2000-11-21 | Cortech, Inc. | Serine protease inhibitors-tripeptoid analogs |
| US5618792A (en) * | 1994-11-21 | 1997-04-08 | Cortech, Inc. | Substituted heterocyclic compounds useful as inhibitors of (serine proteases) human neutrophil elastase |
| US5556990A (en) * | 1994-12-16 | 1996-09-17 | Rhone-Poulenc Rorer Pharmaceuticals Inc. | Polyarylcarbamoylaza- and -carbamoylalkanedioic acids |
| US5872101A (en) * | 1995-01-06 | 1999-02-16 | Sibia Neurosciences, Inc. | Methods of treating neurodegenerative disorders using protease inhibitors |
| US5804560A (en) * | 1995-01-06 | 1998-09-08 | Sibia Neurosciences, Inc. | Peptide and peptide analog protease inhibitors |
| US6369080B2 (en) | 1996-10-11 | 2002-04-09 | Cor Therapeutics, Inc. | Selective factor Xa inhibitors |
| US6262047B1 (en) | 1996-10-11 | 2001-07-17 | Cor Therapeutics, Inc. | Selective factor Xa inhibitors |
| US6194435B1 (en) | 1996-10-11 | 2001-02-27 | Cor Therapeutics, Inc. | Lactams as selective factor Xa inhibitors |
| US6063794A (en) | 1996-10-11 | 2000-05-16 | Cor Therapeutics Inc. | Selective factor Xa inhibitors |
| CA2285659A1 (en) | 1997-04-14 | 1998-10-22 | Cor Therapeutics, Inc. | Selective factor xa inhibitors |
| CA2285705A1 (en) * | 1997-04-14 | 1998-10-22 | Cor Therapeutics, Inc. | Selective factor xa inhibitors |
| EP0977772A1 (en) | 1997-04-14 | 2000-02-09 | Cor Therapeutics, Inc. | SELECTIVE FACTOR Xa INHIBITORS |
| US6274602B1 (en) * | 1998-06-03 | 2001-08-14 | Gpi Nil Holdings, Inc. | Heterocyclic thioester and ketone hair growth compositions and uses |
| US6228854B1 (en) | 1997-08-11 | 2001-05-08 | Cor Therapeutics, Inc. | Selective factor Xa inhibitors |
| US6218382B1 (en) | 1997-08-11 | 2001-04-17 | Cor Therapeutics, Inc | Selective factor Xa inhibitors |
| US6333321B1 (en) | 1997-08-11 | 2001-12-25 | Cor Therapeutics, Inc. | Selective factor Xa inhibitors |
| US6177572B1 (en) | 1997-08-20 | 2001-01-23 | Sepracor, Inc. | Solid and liquid-phase synthesis of benzoxazoles and benzothiazoles and their use |
| US6656910B2 (en) | 1997-12-04 | 2003-12-02 | Cortech, Inc. | Serine protease inhibitors |
| US6184377B1 (en) | 1997-12-15 | 2001-02-06 | Sepracor Inc. | Compositions containing N-amino- and N-hydroxy-quinazolinones and methods for preparing libraries thereof |
| EP1089752A4 (en) | 1998-06-03 | 2002-01-02 | Cortech Inc | ALPHA-KETO OXADIAZOLE AS A SERINE PROTEASE INHIBITOR |
| JP2000256396A (ja) | 1999-03-03 | 2000-09-19 | Dainippon Pharmaceut Co Ltd | 複素環式化合物およびその中間体ならびにエラスターゼ阻害剤 |
| TW200404789A (en) | 1999-03-15 | 2004-04-01 | Axys Pharm Inc | Novel compounds and compositions as protease inhibitors |
| CA2368026A1 (en) * | 1999-03-22 | 2000-09-28 | Bi-Huang Hu | Oxazole and thiazole combinatorial libraries |
| US6569876B1 (en) * | 1999-06-17 | 2003-05-27 | John C. Cheronis | Method and structure for inhibiting activity of serine elastases |
| US7030116B2 (en) | 2000-12-22 | 2006-04-18 | Aventis Pharmaceuticals Inc. | Compounds and compositions as cathepsin inhibitors |
| IL156577A0 (en) | 2000-12-22 | 2004-01-04 | Axys Pharm Inc | Selective cathepsin s inhibitors and pharmaceutical compositions containing the same |
| WO2003024924A1 (en) | 2001-09-14 | 2003-03-27 | Aventis Pharmaceuticals Inc. | Novel compounds and compositions as cathepsin inhibitors |
| RU2004117877A (ru) | 2001-11-14 | 2006-01-10 | Авентис Фармасьютикалз Инк. (Us) | Олигопептиды и композиции, содержащие их, в качестве ингибиторов катепсина s |
| CA2482207A1 (en) * | 2002-04-16 | 2003-10-23 | Axys Pharmaceuticals, Inc. | Process for preparing heteroaryl and unsaturated heterocycloalkylmagnesium reagents and uses |
| JP3744890B2 (ja) | 2002-11-01 | 2006-02-15 | ハッピー工業株式会社 | ミシン |
| JP2009538327A (ja) | 2006-05-23 | 2009-11-05 | アイアールエム・リミテッド・ライアビリティ・カンパニー | チャネル活性化プロテアーゼ阻害剤である化合物および組成物 |
| ATE502951T1 (de) * | 2006-05-23 | 2011-04-15 | Irm Llc | Verbindungen und zusammensetzungen als kanalaktivierende protease-hemmer |
| US8754107B2 (en) * | 2006-11-17 | 2014-06-17 | Abbvie Inc. | Aminopyrrolidines as chemokine receptor antagonists |
| BRPI0807483A2 (pt) | 2007-02-09 | 2014-05-13 | Irm Llc | Compostos e composições como inibidores de protease de ativação de canal |
| FR2914920B1 (fr) | 2007-04-11 | 2011-09-09 | Clariant Specialty Fine Chem F | Procede de deacetalisation d'alpha-aminoacetals. |
| FR2916441B1 (fr) | 2007-05-22 | 2009-08-28 | Clariant Specialty Fine Chem | Procede de racemisation d'alpha-aminoacetals optiquement actifs. |
| US20100273835A1 (en) * | 2007-07-10 | 2010-10-28 | Probiodrug Ag | Novel compounds |
| US20090156509A1 (en) * | 2007-12-12 | 2009-06-18 | Accuthera, Inc. | Tri-peptide Inhibitors of Serine Elastases |
| FR2927900B1 (fr) | 2008-02-27 | 2010-09-17 | Clariant Specialty Fine Chem | Procede de preparation d'alpha-aminoacetals optiquement actifs. |
| CA3165298A1 (en) * | 2019-12-20 | 2021-06-24 | Pfizer Ireland Pharmaceuticals | Efficient process for making 6-carboxy benzoxazole derivatives |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3481913D1 (de) * | 1983-04-27 | 1990-05-17 | Ici America Inc | Prolin-derivate. |
| US4643991A (en) * | 1984-12-18 | 1987-02-17 | The University Of Kentucky Research Foundation | Peptide elastase inhibitors and methods |
| GB8600263D0 (en) * | 1985-01-22 | 1986-02-12 | Ici America Inc | Peptide derivatives |
| EP0204571B1 (en) * | 1985-06-07 | 1992-01-22 | Ici Americas Inc. | Selected difluoro derivatives |
| JPH03505210A (ja) * | 1988-09-09 | 1991-11-14 | ユニバーシティー オブ ケンタッキー リサーチ ファウンデーション | エラスターゼ阻害ポリマーおよび方法 |
| GB8910547D0 (en) * | 1989-05-08 | 1989-06-21 | Ici America Inc | Substituted ketones |
-
1988
- 1988-04-20 GB GB888809316A patent/GB8809316D0/en active Pending
- 1988-04-27 ZA ZA883006A patent/ZA883006B/xx unknown
- 1988-05-01 IL IL8623688A patent/IL86236A/en unknown
- 1988-05-02 AU AU15390/88A patent/AU605284B2/en not_active Ceased
- 1988-05-02 NZ NZ224452A patent/NZ224452A/en unknown
- 1988-05-03 ZW ZW49/88A patent/ZW4988A1/xx unknown
- 1988-05-05 DE DE3888568T patent/DE3888568T2/de not_active Expired - Fee Related
- 1988-05-05 EP EP88304080A patent/EP0291234B1/en not_active Expired - Lifetime
- 1988-05-05 AT AT88304080T patent/ATE103293T1/de not_active IP Right Cessation
- 1988-05-05 ES ES88304080T patent/ES2063034T3/es not_active Expired - Lifetime
- 1988-05-06 SU SU884355719A patent/SU1678207A3/ru active
- 1988-05-09 HU HU882325A patent/HU201963B/hu unknown
- 1988-05-10 IE IE141688A patent/IE62524B1/en not_active IP Right Cessation
- 1988-05-10 FI FI882176A patent/FI91072C/fi not_active IP Right Cessation
- 1988-05-10 NO NO882036A patent/NO176519C/no unknown
- 1988-05-11 DK DK260588A patent/DK260588A/da not_active Application Discontinuation
- 1988-05-11 US US07/193,317 patent/US5164371A/en not_active Expired - Lifetime
- 1988-05-11 JP JP63112693A patent/JPS6445395A/ja active Pending
- 1988-05-11 CN CN88103247A patent/CN1037519A/zh active Pending
- 1988-05-11 PT PT87454A patent/PT87454B/pt not_active IP Right Cessation
- 1988-05-11 KR KR1019880005474A patent/KR880013926A/ko not_active Abandoned
- 1988-05-11 CA CA000566529A patent/CA1326107C/en not_active Expired - Fee Related
Non-Patent Citations (1)
| Title |
|---|
| ЕР Ns 189305, кл.С 07 К 5/06,опубл.1986. * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2319708C2 (ru) * | 2002-02-05 | 2008-03-20 | ДАЙНИППОН СУМИТОМО ФАРМА Ко., ЛТД. | Гетероциклические соединения с эластазоингибирующей активностью и их производные, а также фармацевтическая композиция и средство на их основе |
| EA012727B1 (ru) * | 2004-09-21 | 2009-12-30 | Бёрингер Ингельхайм Интернациональ Гмбх | Гетероарильные соединения в качестве бетамиметиков для лечения заболеваний дыхательных путей |
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