KR100256036B1 - 사이클릭 펩타이드 항진균제 및 그의 제조방법 - Google Patents
사이클릭 펩타이드 항진균제 및 그의 제조방법 Download PDFInfo
- Publication number
- KR100256036B1 KR100256036B1 KR1019930004076A KR930004076A KR100256036B1 KR 100256036 B1 KR100256036 B1 KR 100256036B1 KR 1019930004076 A KR1019930004076 A KR 1019930004076A KR 930004076 A KR930004076 A KR 930004076A KR 100256036 B1 KR100256036 B1 KR 100256036B1
- Authority
- KR
- South Korea
- Prior art keywords
- substituted
- alkyl
- formula
- hydrogen
- phenyl
- 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.)
- Expired - Lifetime
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- 238000000034 method Methods 0.000 title abstract description 29
- 229940121375 antifungal agent Drugs 0.000 title description 25
- 239000003429 antifungal agent Substances 0.000 title description 13
- 108010069514 Cyclic Peptides Proteins 0.000 title description 10
- 102000001189 Cyclic Peptides Human genes 0.000 title description 10
- 238000002360 preparation method Methods 0.000 title description 4
- 230000008569 process Effects 0.000 title description 4
- -1 hydroxysulfonyloxy Chemical group 0.000 claims abstract description 104
- 150000001875 compounds Chemical class 0.000 claims abstract description 78
- 239000001257 hydrogen Substances 0.000 claims abstract description 40
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 40
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 25
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 21
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 21
- 125000002252 acyl group Chemical group 0.000 claims abstract description 20
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 18
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 claims abstract description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 38
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 35
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims description 21
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 14
- 125000006711 (C2-C12) alkynyl group Chemical group 0.000 claims description 13
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 12
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 11
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 10
- 150000001602 bicycloalkyls Chemical group 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 9
- 125000006710 (C2-C12) alkenyl group Chemical group 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical group [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims description 6
- 206010017533 Fungal infection Diseases 0.000 claims description 5
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- 125000004414 alkyl thio group Chemical group 0.000 claims description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
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- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- 231100000252 nontoxic Toxicity 0.000 claims description 4
- 230000003000 nontoxic effect Effects 0.000 claims description 4
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- 206010035664 Pneumonia Diseases 0.000 claims description 3
- 125000005236 alkanoylamino group Chemical group 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 3
- 125000004981 cycloalkylmethyl group Chemical group 0.000 claims description 3
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- 229930195735 unsaturated hydrocarbon Natural products 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 2
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 2
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
- 125000001246 bromo group Chemical group Br* 0.000 claims description 2
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- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 2
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- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
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- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 208000015181 infectious disease Diseases 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 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 11
- 238000011282 treatment Methods 0.000 description 10
- AQRLNPVMDITEJU-UHFFFAOYSA-N triethylsilane Chemical compound CC[SiH](CC)CC AQRLNPVMDITEJU-UHFFFAOYSA-N 0.000 description 10
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000001914 filtration Methods 0.000 description 9
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- 230000000694 effects Effects 0.000 description 7
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- FAUOJMHVEYMQQG-HVYQDZECSA-N echinocandin B Chemical compound C1([C@H](O)[C@@H](O)[C@H]2C(=O)N[C@H](C(=O)N3C[C@H](C)[C@H](O)[C@H]3C(=O)N[C@H](O)[C@H](O)C[C@@H](C(N[C@H](C(=O)N3C[C@H](O)C[C@H]3C(=O)N2)[C@@H](C)O)=O)NC(=O)CCCCCCC\C=C/C\C=C/CCCCC)[C@@H](C)O)=CC=C(O)C=C1 FAUOJMHVEYMQQG-HVYQDZECSA-N 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 5
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 5
- 239000003643 water by type Substances 0.000 description 5
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 4
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- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 3
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- 125000003545 alkoxy group Chemical group 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
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- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000005947 deacylation reaction Methods 0.000 description 3
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 3
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
- C07K7/64—Cyclic peptides containing only normal peptide links
- C07K7/66—Gramicidins S, C; Tyrocidins A, B, C; Related peptides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
- C07K7/50—Cyclic peptides containing at least one abnormal peptide link
- C07K7/54—Cyclic peptides containing at least one abnormal peptide link with at least one abnormal peptide link in the ring
- C07K7/56—Cyclic peptides containing at least one abnormal peptide link with at least one abnormal peptide link in the ring the cyclisation not occurring through 2,4-diamino-butanoic acid
-
- 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
- A61P31/04—Antibacterial agents
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- 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
- A61P31/10—Antimycotics
-
- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Oncology (AREA)
- Public Health (AREA)
- Communicable Diseases (AREA)
- Genetics & Genomics (AREA)
- Biophysics (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Virology (AREA)
- Peptides Or Proteins (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Steroid Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US85411792A | 1992-03-19 | 1992-03-19 | |
| US854,117 | 1992-03-19 | ||
| US99239092A | 1992-12-16 | 1992-12-16 | |
| US992,390 | 1992-12-16 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR930019694A KR930019694A (ko) | 1993-10-18 |
| KR100256036B1 true KR100256036B1 (ko) | 2000-05-01 |
Family
ID=27127211
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019930004076A Expired - Lifetime KR100256036B1 (ko) | 1992-03-19 | 1993-03-17 | 사이클릭 펩타이드 항진균제 및 그의 제조방법 |
Country Status (25)
Families Citing this family (46)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5430018A (en) * | 1991-10-17 | 1995-07-04 | Merck & Co., Inc. | Cyclohexapeptide with basic nitrogen containing alkylamide groups |
| MY136593A (en) * | 1992-03-19 | 2008-10-31 | Lilly Co Eli | Cyclic peptide antifungal agents and process for preparation thereof |
| US6743777B1 (en) | 1992-03-19 | 2004-06-01 | Eli Lilly And Company | Cyclic peptide antifungal agents and process for preparation thereof |
| US5378804A (en) * | 1993-03-16 | 1995-01-03 | Merck & Co., Inc. | Aza cyclohexapeptide compounds |
| US5948753A (en) * | 1993-05-04 | 1999-09-07 | Merck & Co., Inc. | Cyclohexapeptidyl propanolamine compounds |
| AU674233B2 (en) * | 1993-05-04 | 1996-12-12 | Merck & Co., Inc. | Cyclohexapeptidyl aminoalkyl ethers |
| WO1995008341A1 (en) * | 1993-09-22 | 1995-03-30 | Merck & Co., Inc. | Antifungal and anti-pneumocystis compounds, compositions containing such compounds, and methods of use |
| DE69528065T2 (de) * | 1994-09-16 | 2003-04-10 | Merck & Co., Inc. | Azazyklohexapeptid-verbindungen |
| US5514651A (en) * | 1994-09-16 | 1996-05-07 | Merck & Co., Inc. | Aza cyclohexapeptide compounds |
| US5516757A (en) * | 1994-09-16 | 1996-05-14 | Merck & Co., Inc. | Semi-synthetic lipopeptides, compositions containing said lipopeptides, and methods of use |
| DE122008000025I2 (de) * | 1994-10-07 | 2011-02-17 | Astellas Pharma Inc | Zyklische hexapeptide mit antibiotischer aktivität |
| US5516756A (en) * | 1994-10-31 | 1996-05-14 | Merck & Co., Inc. | Aza cyclohexapeptide compounds |
| JP2966936B2 (ja) * | 1995-01-26 | 1999-10-25 | メルク エンド カンパニー インコーポレーテッド | 新規抗真菌シクロヘキサペプチド |
| US5646111A (en) * | 1995-04-07 | 1997-07-08 | Eli Lilly And Company | Cyclic peptide antifungal Agents |
| US5652213A (en) * | 1995-05-26 | 1997-07-29 | Eli Lilly And Company | Cyclic peptide antifungal agents |
| US5618787A (en) * | 1995-05-26 | 1997-04-08 | Eli Lilly And Company | Cyclic peptide antifungal agents |
| US5786325A (en) * | 1995-05-26 | 1998-07-28 | Eli Lilly And Company | Cyclic peptide antifungal agents and methods of making and using |
| US5629290A (en) * | 1995-05-26 | 1997-05-13 | Eli Lilly And Company | Cyclic peptide antifungal agents |
| US5629289A (en) * | 1995-07-25 | 1997-05-13 | Eli Lilly And Company | Cyclic peptide antifungal agents |
| WO1997027864A1 (en) * | 1996-02-01 | 1997-08-07 | Eli Lilly And Company | Cyclic peptide antifungal agents |
| US5693611A (en) * | 1996-02-01 | 1997-12-02 | Eli Lilly And Company | Cyclic peptide antifungal agents |
| JPH09227422A (ja) * | 1996-02-12 | 1997-09-02 | Rolic Ag | シクロペンチル誘導体 |
| US5696084A (en) * | 1996-08-16 | 1997-12-09 | Abbott Laboratories | Amino-lipopetide antifungal agents |
| AUPO381496A0 (en) * | 1996-11-25 | 1996-12-19 | Fujisawa Pharmaceutical Co., Ltd. | New compound |
| AU2003200556B2 (en) * | 1997-12-10 | 2005-12-01 | Novexel | Echinocandin derivative and their preparation method |
| FR2784993B1 (fr) * | 1998-10-26 | 2002-10-31 | Hoechst Marion Roussel Inc | Nouveaux derives de l'echinocandine, leur procede de preparation et leur application comme fongicides |
| UA72200C2 (uk) * | 1997-12-10 | 2005-02-15 | Авентіс Фарма С.А. | Похідні ехінокандину, спосіб їх одержання, їх застосування, проміжні сполуки та фармацевтична композиція |
| AUPP172898A0 (en) * | 1998-02-09 | 1998-03-05 | Fujisawa Pharmaceutical Co., Ltd. | New compound |
| US6730776B1 (en) * | 1998-03-16 | 2004-05-04 | Fujisawa Pharmaceutical Co., Ltd. | WF14573 or its salt, production thereof and use thereof |
| WO2000011023A2 (en) | 1998-08-20 | 2000-03-02 | Eli Lilly And Company | Ring modified cyclic peptide analogs |
| AU766091B2 (en) | 1998-12-09 | 2003-10-09 | Eli Lilly And Company | Purification of echinocandin cyclopeptide compounds |
| DE19907904A1 (de) | 1999-02-24 | 2000-08-31 | Clariant Gmbh | Verfahren zur Herstellung von [1,1':4',1"]-Terphenylverbindungen |
| KR20020002476A (ko) | 1999-03-03 | 2002-01-09 | 피터 지. 스트링거 | 결정질 에키노칸딘 암모늄염의 형성 및 음이온 교환 |
| IL145188A0 (en) | 1999-03-03 | 2002-06-30 | Lilly Co Eli | Processes for making pharmaceutical oral ecb formulations and compositions |
| AU772633B2 (en) | 1999-03-03 | 2004-05-06 | Eli Lilly And Company | Echinocandin/carbohydrate complexes |
| WO2000051564A1 (en) * | 1999-03-03 | 2000-09-08 | Eli Lilly And Company | Echinocandin pharmaceutical formulations containing micelle-forming surfactants |
| DE60112725T2 (de) * | 2000-02-18 | 2006-06-01 | Meiji Seika Kaisha Ltd. | Phenoxyalkylaminderivate als agonisten des opioid-delta rezeptors |
| FR2833596B1 (fr) * | 2001-12-14 | 2005-02-18 | Aventis Pharma Sa | Procede de preparation de derives d'echinocandine |
| US6991800B2 (en) | 2002-06-13 | 2006-01-31 | Vicuron Pharmaceuticals Inc. | Antifungal parenteral products |
| KR20060006954A (ko) * | 2003-04-30 | 2006-01-20 | 디 인스티튜트스 포 파마슈티컬 디스커버리, 엘엘씨 | 단백질 티로신 포스파타제-１ｂ 억제제로서의 페닐 치환된카르복실산 |
| KR101551207B1 (ko) * | 2008-09-04 | 2015-09-08 | 롬엔드하스전자재료코리아유한회사 | 신규한 유기 발광 화합물 및 이를 발광재료로서 채용하고 있는 유기 발광 소자 |
| CN102464704B (zh) * | 2010-11-05 | 2013-12-11 | 上海医药工业研究院 | 一种化合物及其制备方法和用途 |
| HRP20231151T1 (hr) * | 2012-03-19 | 2024-01-05 | Cidara Therapeutics, Inc. | Režimi za doziranje spojeva iz klase ehinokandina |
| PL3058958T3 (pl) | 2015-02-23 | 2019-02-28 | Selectchemie Ag | Kompozycja anidulafunginy |
| JP6866583B2 (ja) * | 2016-07-05 | 2021-04-28 | Dic株式会社 | 液晶化合物 |
| CN116903706B (zh) * | 2023-06-13 | 2024-05-17 | 深圳市祥根生物有限公司 | 一种棘白菌素类药物及其制备方法和用途 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE886576A (fr) * | 1979-12-13 | 1981-06-10 | Lilly Co Eli | Derives de noyaux peptidiques cycliques, leur preparation et leur utilisation comme agents antifongiques |
| BE886575A (fr) * | 1979-12-13 | 1981-06-10 | Lilly Co Eli | Derives de noyaux peptidiques cycliques, leur preparation et leur utilisation comme agents antifongiques |
| CA2037957A1 (en) * | 1990-03-12 | 1991-09-13 | Merck & Co., Inc. | N-acylated cyclohexapeptide compounds |
| GB2241956A (en) * | 1990-03-16 | 1991-09-18 | Merck & Co Inc | N-acylated cyclohexapeptide compounds |
| US5330973A (en) * | 1990-03-19 | 1994-07-19 | Merck & Co., Inc. | Lipopeptide derivatives |
| US5310726A (en) * | 1990-03-19 | 1994-05-10 | Merck & Co., Inc. | Lipopeptide compounds |
| IL97347A0 (en) * | 1990-03-19 | 1992-05-25 | Merck & Co Inc | Lipopeptide derivatives and antimicrobial compositions containing them |
| MY136593A (en) * | 1992-03-19 | 2008-10-31 | Lilly Co Eli | Cyclic peptide antifungal agents and process for preparation thereof |
-
1993
- 1993-03-15 MY MYPI93000458A patent/MY136593A/en unknown
- 1993-03-15 NZ NZ299314A patent/NZ299314A/en not_active IP Right Cessation
- 1993-03-15 IL IL10504893A patent/IL105048A/en active Protection Beyond IP Right Term
- 1993-03-15 CZ CZ1993416A patent/CZ288974B6/cs not_active IP Right Cessation
- 1993-03-15 TW TW082101890A patent/TW264477B/zh not_active IP Right Cessation
- 1993-03-15 NZ NZ247149A patent/NZ247149A/en not_active IP Right Cessation
- 1993-03-15 CA CA002091663A patent/CA2091663C/en not_active Expired - Lifetime
- 1993-03-15 IL IL12231593A patent/IL122315A/en not_active IP Right Cessation
- 1993-03-15 NZ NZ512085A patent/NZ512085A/en not_active IP Right Cessation
- 1993-03-16 MX MX9301457A patent/MX9301457A/es unknown
- 1993-03-16 NO NO93930948A patent/NO930948L/no not_active Application Discontinuation
- 1993-03-17 KR KR1019930004076A patent/KR100256036B1/ko not_active Expired - Lifetime
- 1993-03-18 BR BR9301232A patent/BR9301232A/pt not_active Application Discontinuation
- 1993-03-18 PT PT93302064T patent/PT561639E/pt unknown
- 1993-03-18 AT AT93302064T patent/ATE217635T1/de active
- 1993-03-18 EP EP93302064A patent/EP0561639B1/en not_active Expired - Lifetime
- 1993-03-18 HU HU9300785A patent/HU225783B1/hu unknown
- 1993-03-18 CN CN93103587A patent/CN1036715C/zh not_active Expired - Lifetime
- 1993-03-18 FI FI931202A patent/FI118768B/fi not_active IP Right Cessation
- 1993-03-18 DE DE69331922T patent/DE69331922T2/de not_active Expired - Lifetime
- 1993-03-18 DE DE200812000006 patent/DE122008000006I2/de active Active
- 1993-03-18 DK DK93302064T patent/DK0561639T3/da active
- 1993-03-18 JP JP05852993A patent/JP3519754B2/ja not_active Expired - Lifetime
- 1993-03-18 YU YU18593A patent/YU49108B/sh unknown
- 1993-03-18 RU RU93004787A patent/RU2129562C1/ru active
- 1993-03-18 ES ES93302064T patent/ES2174843T3/es not_active Expired - Lifetime
- 1993-03-19 AU AU35341/93A patent/AU3534193A/en not_active Abandoned
-
1995
- 1995-06-22 HU HU95P/P00378P patent/HU211562A9/hu active Protection Beyond IP Right Term
-
1996
- 1996-09-09 AU AU65529/96A patent/AU689391B2/en not_active Expired
-
1997
- 1997-11-27 IL IL12231597A patent/IL122315A0/xx unknown
-
2002
- 2002-01-10 JP JP2002003969A patent/JP3520071B2/ja not_active Expired - Lifetime
-
2003
- 2003-12-10 JP JP2003412638A patent/JP2004115540A/ja active Pending
-
2008
- 2008-01-09 LU LU91406C patent/LU91406I2/fr unknown
- 2008-01-21 NL NL300334C patent/NL300334I2/nl unknown
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