DE2704030A1 - Neue organische verbindungen, ihre herstellung und verwendung - Google Patents
Neue organische verbindungen, ihre herstellung und verwendungInfo
- Publication number
- DE2704030A1 DE2704030A1 DE19772704030 DE2704030A DE2704030A1 DE 2704030 A1 DE2704030 A1 DE 2704030A1 DE 19772704030 DE19772704030 DE 19772704030 DE 2704030 A DE2704030 A DE 2704030A DE 2704030 A1 DE2704030 A1 DE 2704030A1
- Authority
- DE
- Germany
- Prior art keywords
- formula
- carbon atoms
- compound
- above meaning
- alkyl
- 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.)
- Pending
Links
- 238000004519 manufacturing process Methods 0.000 title description 3
- 150000002894 organic compounds Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 33
- 125000004432 carbon atom Chemical group C* 0.000 claims description 24
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 239000001257 hydrogen Substances 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 17
- 239000002253 acid Substances 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 150000002431 hydrogen Chemical class 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 150000003254 radicals Chemical class 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 4
- -1 tetrahydrofurylmethyl Chemical group 0.000 claims description 4
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 3
- 125000004848 alkoxyethyl group Chemical group 0.000 claims description 3
- 238000007327 hydrogenolysis reaction Methods 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 125000006239 protecting group Chemical group 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 48
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
- 229960000583 acetic acid Drugs 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- 239000012362 glacial acetic acid Substances 0.000 description 10
- 239000000741 silica gel Substances 0.000 description 10
- 229910002027 silica gel Inorganic materials 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 9
- 239000000843 powder Substances 0.000 description 8
- 239000003054 catalyst Substances 0.000 description 7
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- SIHHLZPXQLFPMC-UHFFFAOYSA-N chloroform;methanol;hydrate Chemical compound O.OC.ClC(Cl)Cl SIHHLZPXQLFPMC-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 5
- 238000010828 elution Methods 0.000 description 5
- 108010001001 tetrahydroechinocandin B Proteins 0.000 description 5
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 5
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 229910052763 palladium Inorganic materials 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- CSFSSKWGOYOSPM-UHFFFAOYSA-N tetrahydroechinocandin b Chemical class N1C(=O)C2CC(O)CN2C(=O)C(C(C)O)NC(=O)C(NC(=O)CCCCCCCCCCCCCCCCC)CC(O)C(O)NC(=O)C2C(O)C(C)CN2C(=O)C(C(C)O)NC(=O)C1C(O)C(O)C1=CC=C(O)C=C1 CSFSSKWGOYOSPM-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 3
- WGXZDYPGLJYBJW-UHFFFAOYSA-N chloroform;propan-2-ol Chemical compound CC(C)O.ClC(Cl)Cl WGXZDYPGLJYBJW-UHFFFAOYSA-N 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 208000031888 Mycoses Diseases 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 150000001242 acetic acid derivatives Chemical class 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000002808 molecular sieve Substances 0.000 description 2
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 2
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 1
- FPYUJUBAXZAQNL-UHFFFAOYSA-N 2-chlorobenzaldehyde Chemical compound ClC1=CC=CC=C1C=O FPYUJUBAXZAQNL-UHFFFAOYSA-N 0.000 description 1
- PMUNIMVZCACZBB-UHFFFAOYSA-N 2-hydroxyethylazanium;chloride Chemical compound Cl.NCCO PMUNIMVZCACZBB-UHFFFAOYSA-N 0.000 description 1
- 108010049047 Echinocandins Proteins 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- 229920005654 Sephadex Polymers 0.000 description 1
- 239000012507 Sephadex™ Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000001414 amino alcohols Chemical class 0.000 description 1
- 230000000843 anti-fungal effect Effects 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- SAGINAGERRNGGV-UHFFFAOYSA-N benzyl n-(2-hydroxyethyl)carbamate Chemical compound OCCNC(=O)OCC1=CC=CC=C1 SAGINAGERRNGGV-UHFFFAOYSA-N 0.000 description 1
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 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 1
- 108010062092 echinocandin B Proteins 0.000 description 1
- XBRDBODLCHKXHI-UHFFFAOYSA-N epolamine Chemical compound OCCN1CCCC1 XBRDBODLCHKXHI-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000008098 formaldehyde solution Substances 0.000 description 1
- 238000002523 gelfiltration Methods 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229940126601 medicinal product Drugs 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- 244000052769 pathogen Species 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000005932 reductive alkylation reaction Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229940066768 systemic antihistamines aminoalkyl ethers Drugs 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 238000010626 work up procedure Methods 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
- A61P31/04—Antibacterial agents
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Oncology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Biochemistry (AREA)
- Communicable Diseases (AREA)
- Biophysics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Genetics & Genomics (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH170676 | 1976-02-12 | ||
| CH340376 | 1976-03-18 | ||
| CH1446876 | 1976-11-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2704030A1 true DE2704030A1 (de) | 1977-08-18 |
Family
ID=27173191
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19772704030 Pending DE2704030A1 (de) | 1976-02-12 | 1977-02-01 | Neue organische verbindungen, ihre herstellung und verwendung |
Country Status (11)
| Country | Link |
|---|---|
| JP (1) | JPS52116496A (https=) |
| AU (1) | AU2222977A (https=) |
| DE (1) | DE2704030A1 (https=) |
| DK (1) | DK46577A (https=) |
| ES (1) | ES455791A1 (https=) |
| FI (1) | FI770377A7 (https=) |
| FR (1) | FR2340947A1 (https=) |
| IL (1) | IL51426A0 (https=) |
| NL (1) | NL7701295A (https=) |
| PT (1) | PT66186B (https=) |
| SE (1) | SE7701155L (https=) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2458551A1 (fr) * | 1979-06-08 | 1981-01-02 | Lilly Co Eli | Nouveaux antibiotiques, leur preparation et leur utilisation |
| FR2476074A1 (fr) * | 1979-12-13 | 1981-08-21 | Lilly Co Eli | Derives de noyaux peptidiques cycliques, leur preparation et leur utilisation comme agents antifongiques |
| EP0031221B1 (en) * | 1979-12-13 | 1983-03-02 | Eli Lilly And Company | Cyclic peptide nuclei |
| EP0808330B1 (en) * | 1995-02-10 | 2005-11-09 | Merck & Co., Inc. | A process for preparing certain aza cyclohexapeptides |
| WO2021110125A1 (zh) * | 2019-12-06 | 2021-06-10 | 上海森辉医药有限公司 | 棘白菌素类似物及其制备方法 |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2742435A1 (de) * | 1976-09-28 | 1978-04-06 | Sandoz Ag | Aminoalkylaether der peptide tetrahydro- sl 7810/f-ii, s 31794/f-1, aculeacin a und tetrahydroechinocandin b, ihre verwendung und herstellung |
| US4803261A (en) * | 1986-06-27 | 1989-02-07 | The Administrators Of The Tulane Educational Fund | Method for synthesizing a peptide containing a non-peptide |
| US5055479A (en) * | 1988-06-16 | 1991-10-08 | Sankyo Company, Limited | Method of treating cachexia |
| US6030944A (en) * | 1991-10-01 | 2000-02-29 | Merck & Co., Inc. | Cyclohexapeptidyl bisamine compounds |
| US5378804A (en) * | 1993-03-16 | 1995-01-03 | Merck & Co., Inc. | Aza cyclohexapeptide compounds |
-
1977
- 1977-02-01 DE DE19772704030 patent/DE2704030A1/de active Pending
- 1977-02-03 FI FI770377A patent/FI770377A7/fi not_active Application Discontinuation
- 1977-02-03 DK DK46577A patent/DK46577A/da not_active Application Discontinuation
- 1977-02-03 SE SE7701155A patent/SE7701155L/xx unknown
- 1977-02-08 NL NL7701295A patent/NL7701295A/xx not_active Application Discontinuation
- 1977-02-10 ES ES455791A patent/ES455791A1/es not_active Expired
- 1977-02-10 FR FR7703706A patent/FR2340947A1/fr not_active Withdrawn
- 1977-02-10 JP JP1315077A patent/JPS52116496A/ja active Pending
- 1977-02-11 IL IL51426A patent/IL51426A0/xx unknown
- 1977-02-11 PT PT66186A patent/PT66186B/pt unknown
- 1977-02-11 AU AU22229/77A patent/AU2222977A/en not_active Expired
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2458551A1 (fr) * | 1979-06-08 | 1981-01-02 | Lilly Co Eli | Nouveaux antibiotiques, leur preparation et leur utilisation |
| FR2476074A1 (fr) * | 1979-12-13 | 1981-08-21 | Lilly Co Eli | Derives de noyaux peptidiques cycliques, leur preparation et leur utilisation comme agents antifongiques |
| EP0031221B1 (en) * | 1979-12-13 | 1983-03-02 | Eli Lilly And Company | Cyclic peptide nuclei |
| EP0808330B1 (en) * | 1995-02-10 | 2005-11-09 | Merck & Co., Inc. | A process for preparing certain aza cyclohexapeptides |
| WO2021110125A1 (zh) * | 2019-12-06 | 2021-06-10 | 上海森辉医药有限公司 | 棘白菌素类似物及其制备方法 |
| CN114616238A (zh) * | 2019-12-06 | 2022-06-10 | 上海森辉医药有限公司 | 棘白菌素类似物及其制备方法 |
| CN114616238B (zh) * | 2019-12-06 | 2025-04-11 | 福建盛迪医药有限公司 | 棘白菌素类似物及其制备方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| PT66186B (fr) | 1978-10-13 |
| NL7701295A (nl) | 1977-08-16 |
| AU2222977A (en) | 1978-08-17 |
| DK46577A (da) | 1977-08-13 |
| PT66186A (fr) | 1977-03-01 |
| FI770377A7 (https=) | 1977-08-13 |
| IL51426A0 (en) | 1977-04-29 |
| SE7701155L (sv) | 1977-08-13 |
| ES455791A1 (es) | 1978-11-01 |
| JPS52116496A (en) | 1977-09-29 |
| FR2340947A1 (fr) | 1977-09-09 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHJ | Non-payment of the annual fee |