UA64787C2 - A process for the conversion of echinocandin class of peptides to their c4-homotyrosine monodeoxy analogues - Google Patents
A process for the conversion of echinocandin class of peptides to their c4-homotyrosine monodeoxy analogues Download PDFInfo
- Publication number
- UA64787C2 UA64787C2 UA2000116619A UA2000116619A UA64787C2 UA 64787 C2 UA64787 C2 UA 64787C2 UA 2000116619 A UA2000116619 A UA 2000116619A UA 2000116619 A UA2000116619 A UA 2000116619A UA 64787 C2 UA64787 C2 UA 64787C2
- Authority
- UA
- Ukraine
- Prior art keywords
- snoasomn
- deoxypneumocandin
- pneumocandin
- monodeoxy
- homotyrosine
- Prior art date
Links
- 108010049047 Echinocandins Proteins 0.000 title claims abstract description 25
- 238000000034 method Methods 0.000 title claims abstract description 15
- 108090000765 processed proteins & peptides Proteins 0.000 title claims abstract description 8
- 102000004196 processed proteins & peptides Human genes 0.000 title claims abstract description 8
- 238000006243 chemical reaction Methods 0.000 title claims abstract description 4
- GWBOEEVOSDBARW-SPXLVGSKSA-N C([C@@H](O)[C@H]1C(=O)N[C@@H](CO)C(=O)N2C[C@H](C)[C@H](O)[C@H]2C(=O)N[C@H](O)[C@H](O)C[C@@H](C(N[C@H](C(=O)N2C[C@H](O)C[C@H]2C(=O)N1)[C@@H](C)O)=O)NC(=O)CCCCCCCCCCC(C)CC)C1=CC=C(O)C=C1 Chemical compound C([C@@H](O)[C@H]1C(=O)N[C@@H](CO)C(=O)N2C[C@H](C)[C@H](O)[C@H]2C(=O)N[C@H](O)[C@H](O)C[C@@H](C(N[C@H](C(=O)N2C[C@H](O)C[C@H]2C(=O)N1)[C@@H](C)O)=O)NC(=O)CCCCCCCCCCC(C)CC)C1=CC=C(O)C=C1 GWBOEEVOSDBARW-SPXLVGSKSA-N 0.000 claims abstract description 15
- 108010063315 deoxymulundocandin Proteins 0.000 claims abstract description 15
- WUPSJTQKGFMDON-UHFFFAOYSA-N Mulundocandin Natural products N1C(=O)C2CC(O)CN2C(=O)C(C(C)O)NC(=O)C(NC(=O)CCCCCCCCCCC(C)CC)CC(O)C(O)NC(=O)C2C(O)C(C)CN2C(=O)C(CO)NC(=O)C1C(O)C(O)C1=CC=C(O)C=C1 WUPSJTQKGFMDON-UHFFFAOYSA-N 0.000 claims abstract description 13
- WUPSJTQKGFMDON-FUMJLYDLSA-N N-[(3S,6S,9S,11R,15S,18S,20R,21R,24S,25S,26S)-6-[(1S)-1,2-dihydroxy-2-(4-hydroxyphenyl)ethyl]-11,20,21,25-tetrahydroxy-15-[(1R)-1-hydroxyethyl]-3-(hydroxymethyl)-26-methyl-2,5,8,14,17,23-hexaoxo-1,4,7,13,16,22-hexazatricyclo[22.3.0.09,13]heptacosan-18-yl]-12-methyltetradecanamide Chemical compound CCC(C)CCCCCCCCCCC(=O)N[C@H]1C[C@@H](O)[C@@H](O)NC(=O)[C@@H]2[C@@H](O)[C@@H](C)CN2C(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@@H]2C[C@@H](O)CN2C(=O)[C@@H](NC1=O)[C@@H](C)O)[C@H](O)C(O)c1ccc(O)cc1 WUPSJTQKGFMDON-FUMJLYDLSA-N 0.000 claims abstract description 13
- 108010084578 mulundocandin Proteins 0.000 claims abstract description 13
- 150000001875 compounds Chemical class 0.000 claims abstract description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 8
- LOOZZTFGSTZNRX-VIFPVBQESA-N L-Homotyrosine Chemical compound OC(=O)[C@@H](N)CCC1=CC=C(O)C=C1 LOOZZTFGSTZNRX-VIFPVBQESA-N 0.000 claims abstract description 4
- AHLPHDHHMVZTML-BYPYZUCNSA-N L-Ornithine Chemical compound NCCC[C@H](N)C(O)=O AHLPHDHHMVZTML-BYPYZUCNSA-N 0.000 claims abstract description 4
- AHLPHDHHMVZTML-UHFFFAOYSA-N Orn-delta-NH2 Natural products NCCCC(N)C(O)=O AHLPHDHHMVZTML-UHFFFAOYSA-N 0.000 claims abstract description 4
- UTJLXEIPEHZYQJ-UHFFFAOYSA-N Ornithine Natural products OC(=O)C(C)CCCN UTJLXEIPEHZYQJ-UHFFFAOYSA-N 0.000 claims abstract description 4
- 230000007935 neutral effect Effects 0.000 claims abstract description 4
- 229960003104 ornithine Drugs 0.000 claims abstract description 4
- 239000011541 reaction mixture Substances 0.000 claims abstract description 4
- 238000010511 deprotection reaction Methods 0.000 claims abstract description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 17
- -1 10,12-Dimethylmyristoyl Chemical group 0.000 claims description 7
- 229910000564 Raney nickel Inorganic materials 0.000 claims description 7
- 239000007868 Raney catalyst Substances 0.000 claims description 6
- 125000002669 linoleoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
- 238000007327 hydrogenolysis reaction Methods 0.000 claims description 4
- 108010062096 echinocandin C Proteins 0.000 claims description 3
- NZZDHXBKVFENNY-YBPCKFEPSA-N echinocandin c Chemical compound C([C@@H](O)[C@H]1C(=O)N[C@H](C(=O)N2C[C@H](C)[C@H](O)[C@H]2C(=O)N[C@H](O)[C@H](O)C[C@@H](C(N[C@H](C(=O)N2C[C@H](O)C[C@H]2C(=O)N1)[C@@H](C)O)=O)NC(=O)CCCCCCC\C=C/C\C=C/CCCCC)[C@@H](C)O)C1=CC=C(O)C=C1 NZZDHXBKVFENNY-YBPCKFEPSA-N 0.000 claims description 3
- DFQUSLQYURJBIT-KGPSKUFKSA-N pneumocandin ao 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)CCCCCCCC[C@@H](C)C[C@@H](C)CC)[C@H](O)CC(N)=O)=CC=C(O)C=C1 DFQUSLQYURJBIT-KGPSKUFKSA-N 0.000 claims description 3
- 108010062092 echinocandin B Proteins 0.000 claims description 2
- 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 claims description 2
- 238000002955 isolation Methods 0.000 claims description 2
- CAUDURDUCQQHDE-UVQGGVJESA-N pneumocandin b2 Chemical compound C1([C@@H](O)C(O)[C@H]2C(=O)N[C@H](C(=O)N3CC[C@H](O)[C@H]3C(=O)NCCCC(C(N[C@H](C(=O)N3C[C@H](O)C[C@H]3C(=O)N2)[C@@H](C)O)=O)NC(=O)CCCCCCCCC(C)CC(C)CC)[C@H](O)CC(N)=O)=CC=C(O)C=C1 CAUDURDUCQQHDE-UVQGGVJESA-N 0.000 claims description 2
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims 2
- 238000006722 reduction reaction Methods 0.000 claims 2
- 238000000746 purification Methods 0.000 abstract description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 125000001419 myristoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 230000005526 G1 to G0 transition Effects 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 229920001503 Glucan Polymers 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 206010035742 Pneumonitis Diseases 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 230000000843 anti-fungal effect Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000004185 countercurrent chromatography Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 238000010828 elution Methods 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 238000004460 liquid liquid chromatography Methods 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 208000029462 Immunodeficiency disease Diseases 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 206010035664 Pneumonia Diseases 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 229940121375 antifungal agent Drugs 0.000 description 1
- 239000003429 antifungal agent Substances 0.000 description 1
- 230000001174 ascending effect Effects 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 230000001010 compromised effect Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 238000005227 gel permeation chromatography Methods 0.000 description 1
- 230000036039 immunity Effects 0.000 description 1
- 229960003444 immunosuppressant agent Drugs 0.000 description 1
- 239000003018 immunosuppressive agent Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 244000039328 opportunistic pathogen Species 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- RTMQLLLPNLXDSP-LORNMRFGSA-N pneumocandin a2 Chemical compound C1([C@@H](O)C(O)[C@H]2C(=O)N[C@H](C(=O)N3C[C@H](C)[C@H](O)[C@H]3C(=O)NCCCC(C(N[C@H](C(=O)N3C[C@H](O)C[C@H]3C(=O)N2)[C@@H](C)O)=O)NC(=O)CCCCCCCCC(C)CC(C)CC)[C@H](O)CC(N)=O)=CC=C(O)C=C1 RTMQLLLPNLXDSP-LORNMRFGSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 238000004366 reverse phase liquid chromatography Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000010414 supernatant solution Substances 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
Classifications
-
- 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
- A61P31/10—Antimycotics
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S930/00—Peptide or protein sequence
- Y10S930/01—Peptide or protein sequence
- Y10S930/19—Antibiotic
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S930/00—Peptide or protein sequence
- Y10S930/01—Peptide or protein sequence
- Y10S930/27—Cyclic peptide or cyclic protein
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)
- Biochemistry (AREA)
- Biophysics (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Animal Behavior & Ethology (AREA)
- Oncology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Communicable Diseases (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Peptides Or Proteins (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP98107397 | 1998-04-23 | ||
| PCT/EP1999/002715 WO1999055727A1 (en) | 1998-04-23 | 1999-04-22 | A process for the conversion of echinocandin class of peptides to their c4-homotyrosine monodeoxy analogues |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| UA64787C2 true UA64787C2 (en) | 2004-03-15 |
Family
ID=8231807
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| UA2000116619A UA64787C2 (en) | 1998-04-23 | 1999-04-22 | A process for the conversion of echinocandin class of peptides to their c4-homotyrosine monodeoxy analogues |
Country Status (34)
| Country | Link |
|---|---|
| US (1) | US6809177B1 (tr) |
| EP (1) | EP1073675B1 (tr) |
| JP (1) | JP2002513033A (tr) |
| KR (1) | KR20010042916A (tr) |
| CN (1) | CN1298410A (tr) |
| AP (1) | AP1111A (tr) |
| AT (1) | ATE350392T1 (tr) |
| AU (1) | AU758395B2 (tr) |
| BG (1) | BG104772A (tr) |
| BR (1) | BR9909853A (tr) |
| CA (1) | CA2327474A1 (tr) |
| CY (1) | CY1106456T1 (tr) |
| CZ (1) | CZ293547B6 (tr) |
| DE (1) | DE69934683T2 (tr) |
| DK (1) | DK1073675T3 (tr) |
| EA (1) | EA002909B1 (tr) |
| EE (1) | EE200000611A (tr) |
| ES (1) | ES2280119T3 (tr) |
| GE (1) | GEP20032900B (tr) |
| HR (1) | HRP20000719A2 (tr) |
| HU (1) | HUP0102491A3 (tr) |
| ID (1) | ID27026A (tr) |
| IL (1) | IL138432A0 (tr) |
| NO (1) | NO20005258L (tr) |
| NZ (1) | NZ506667A (tr) |
| PL (1) | PL343484A1 (tr) |
| PT (1) | PT1073675E (tr) |
| SI (1) | SI1073675T1 (tr) |
| SK (1) | SK15642000A3 (tr) |
| TR (1) | TR200003058T2 (tr) |
| UA (1) | UA64787C2 (tr) |
| WO (1) | WO1999055727A1 (tr) |
| YU (1) | YU65000A (tr) |
| ZA (1) | ZA200004600B (tr) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101993477B (zh) * | 2009-08-18 | 2014-03-26 | 上海医药工业研究院 | 一种棘白菌素b的脱氧类似物的制备方法 |
| BR112012024826B8 (pt) * | 2010-03-29 | 2021-05-25 | Biocon Ltd | processo para purificação de pneumocandina |
| 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 |
| CN116925187A (zh) * | 2022-04-07 | 2023-10-24 | 浙江大学 | 棘白菌素类化合物及其制备方法和用途 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5159059A (en) * | 1990-05-29 | 1992-10-27 | Merck & Co., Inc. | Process for reduction of certain cyclohexapeptide compounds |
| US5939384A (en) * | 1991-10-01 | 1999-08-17 | Merck & Co., Inc. | Cyclohexapeptidyl propanolamine compounds |
| US5348940A (en) * | 1991-10-01 | 1994-09-20 | Merck & Co., Inc. | Cyclohexapeptidyl hydroxypropionitrile compounds |
| AU681119B2 (en) | 1993-05-17 | 1997-08-21 | Fujisawa Pharmaceutical Co., Ltd. | New polypeptide compound and a process for preparation thereof |
| AU692043B2 (en) * | 1994-08-23 | 1998-05-28 | Merck & Co., Inc. | An improved process for preparing side chain derivatives of cyclohexapeptidyl lipopeptides |
| ATE223226T1 (de) * | 1994-09-16 | 2002-09-15 | Merck & Co Inc | Azazyklohexapeptid-verbindungen |
| WO1996015142A1 (en) * | 1994-11-15 | 1996-05-23 | Eli Lilly And Company | Process for performing retro-aldol reaction |
-
1999
- 1999-04-22 DE DE69934683T patent/DE69934683T2/de not_active Expired - Fee Related
- 1999-04-22 BR BR9909853-9A patent/BR9909853A/pt not_active Application Discontinuation
- 1999-04-22 GE GEAP19995615A patent/GEP20032900B/en unknown
- 1999-04-22 PL PL99343484A patent/PL343484A1/xx not_active IP Right Cessation
- 1999-04-22 JP JP2000545885A patent/JP2002513033A/ja active Pending
- 1999-04-22 HU HU0102491A patent/HUP0102491A3/hu unknown
- 1999-04-22 KR KR1020007011728A patent/KR20010042916A/ko not_active Application Discontinuation
- 1999-04-22 WO PCT/EP1999/002715 patent/WO1999055727A1/en active IP Right Grant
- 1999-04-22 CN CN99805330A patent/CN1298410A/zh active Pending
- 1999-04-22 NZ NZ506667A patent/NZ506667A/xx unknown
- 1999-04-22 CZ CZ20003903A patent/CZ293547B6/cs not_active IP Right Cessation
- 1999-04-22 SI SI9930951T patent/SI1073675T1/sl unknown
- 1999-04-22 UA UA2000116619A patent/UA64787C2/uk unknown
- 1999-04-22 US US09/673,836 patent/US6809177B1/en not_active Expired - Fee Related
- 1999-04-22 PT PT99919261T patent/PT1073675E/pt unknown
- 1999-04-22 YU YU65000A patent/YU65000A/sh unknown
- 1999-04-22 AT AT99919261T patent/ATE350392T1/de not_active IP Right Cessation
- 1999-04-22 ID IDW20002148A patent/ID27026A/id unknown
- 1999-04-22 TR TR2000/03058T patent/TR200003058T2/tr unknown
- 1999-04-22 EA EA200001099A patent/EA002909B1/ru not_active IP Right Cessation
- 1999-04-22 DK DK99919261T patent/DK1073675T3/da active
- 1999-04-22 SK SK1564-2000A patent/SK15642000A3/sk unknown
- 1999-04-22 EP EP99919261A patent/EP1073675B1/en not_active Expired - Lifetime
- 1999-04-22 ES ES99919261T patent/ES2280119T3/es not_active Expired - Lifetime
- 1999-04-22 AU AU37096/99A patent/AU758395B2/en not_active Ceased
- 1999-04-22 IL IL13843299A patent/IL138432A0/xx unknown
- 1999-04-22 EE EEP200000611A patent/EE200000611A/xx unknown
- 1999-04-22 AP APAP/P/2000/001894A patent/AP1111A/en active
- 1999-04-22 CA CA002327474A patent/CA2327474A1/en not_active Abandoned
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2000
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- 2000-09-18 BG BG104772A patent/BG104772A/xx unknown
- 2000-10-19 NO NO20005258A patent/NO20005258L/no not_active Application Discontinuation
- 2000-10-23 HR HR20000719A patent/HRP20000719A2/hr not_active Application Discontinuation
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2007
- 2007-03-22 CY CY20071100402T patent/CY1106456T1/el unknown
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