FI107535B - Makrolidien sokerijohdannaiset - Google Patents
Makrolidien sokerijohdannaiset Download PDFInfo
- Publication number
- FI107535B FI107535B FI944017A FI944017A FI107535B FI 107535 B FI107535 B FI 107535B FI 944017 A FI944017 A FI 944017A FI 944017 A FI944017 A FI 944017A FI 107535 B FI107535 B FI 107535B
- Authority
- FI
- Finland
- Prior art keywords
- formula
- compound
- benzyl
- alkyl
- phenyl
- Prior art date
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- 235000000346 sugar Nutrition 0.000 title description 31
- 239000003120 macrolide antibiotic agent Substances 0.000 title description 27
- 229940041033 macrolides Drugs 0.000 title description 11
- 150000001875 compounds Chemical class 0.000 claims description 100
- 238000000034 method Methods 0.000 claims description 43
- 239000002904 solvent Substances 0.000 claims description 39
- 238000006243 chemical reaction Methods 0.000 claims description 29
- 238000002360 preparation method Methods 0.000 claims description 21
- 230000008569 process Effects 0.000 claims description 19
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
- 125000003545 alkoxy group Chemical group 0.000 claims description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 14
- 125000005843 halogen group Chemical group 0.000 claims description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
- 239000012442 inert solvent Substances 0.000 claims description 11
- -1 t-V ·: 35 nyl Chemical group 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 125000004076 pyridyl group Chemical group 0.000 claims description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
- 239000003054 catalyst Substances 0.000 claims description 5
- 238000003756 stirring Methods 0.000 claims description 5
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 claims description 4
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 claims description 4
- 125000001544 thienyl group Chemical group 0.000 claims description 4
- 150000004703 alkoxides Chemical class 0.000 claims description 3
- 230000003197 catalytic effect Effects 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- QRUBYZBWAOOHSV-UHFFFAOYSA-M silver trifluoromethanesulfonate Chemical compound [Ag+].[O-]S(=O)(=O)C(F)(F)F QRUBYZBWAOOHSV-UHFFFAOYSA-M 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 239000002274 desiccant Substances 0.000 claims description 2
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- 235000019341 magnesium sulphate Nutrition 0.000 claims description 2
- 150000004799 α-ketoamides Chemical class 0.000 claims description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 5
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 5
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 3
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 3
- RBWNDBNSJFCLBZ-UHFFFAOYSA-N 7-methyl-5,6,7,8-tetrahydro-3h-[1]benzothiolo[2,3-d]pyrimidine-4-thione Chemical compound N1=CNC(=S)C2=C1SC1=C2CCC(C)C1 RBWNDBNSJFCLBZ-UHFFFAOYSA-N 0.000 claims 1
- 239000001175 calcium sulphate Substances 0.000 claims 1
- 235000011132 calcium sulphate Nutrition 0.000 claims 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 claims 1
- 229910052753 mercury Inorganic materials 0.000 claims 1
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- 210000001519 tissue Anatomy 0.000 description 10
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- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 6
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- 150000002148 esters Chemical class 0.000 description 1
- SLFUXNFVAANERW-UHFFFAOYSA-N ethyl hexanoate;potassium Chemical compound [K].CCCCCC(=O)OCC SLFUXNFVAANERW-UHFFFAOYSA-N 0.000 description 1
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- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
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- 150000002440 hydroxy compounds Chemical class 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 229960003444 immunosuppressant agent Drugs 0.000 description 1
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- HIJSSUKZLPXDPU-UHFFFAOYSA-L mercury(2+);carbonate Chemical compound [Hg+2].[O-]C([O-])=O HIJSSUKZLPXDPU-UHFFFAOYSA-L 0.000 description 1
- AXLHVTKGDPVANO-UHFFFAOYSA-N methyl 2-amino-3-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate Chemical compound COC(=O)C(N)CNC(=O)OC(C)(C)C AXLHVTKGDPVANO-UHFFFAOYSA-N 0.000 description 1
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- ACYBVNYNIZTUIL-UHFFFAOYSA-N n'-benzylethane-1,2-diamine Chemical compound NCCNCC1=CC=CC=C1 ACYBVNYNIZTUIL-UHFFFAOYSA-N 0.000 description 1
- SAVQQRYWWAGSQW-UHFFFAOYSA-N n-methyl-n-(trifluoro-$l^{4}-sulfanyl)methanamine Chemical compound CN(C)S(F)(F)F SAVQQRYWWAGSQW-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- CFZGEMKIQUVTCC-UHFFFAOYSA-N octacos-18-ene-2,3,10,16-tetrone Chemical compound CCCCCCCCCC=CCC(=O)CCCCCC(=O)CCCCCCC(=O)C(C)=O CFZGEMKIQUVTCC-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 235000019371 penicillin G benzathine Nutrition 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 239000003223 protective agent Substances 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 239000012449 sabouraud dextrose agar Substances 0.000 description 1
- 238000013207 serial dilution Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910001961 silver nitrate Inorganic materials 0.000 description 1
- BABPEPRNSRIYFA-UHFFFAOYSA-N silyl trifluoromethanesulfonate Chemical compound FC(F)(F)S(=O)(=O)O[SiH3] BABPEPRNSRIYFA-UHFFFAOYSA-N 0.000 description 1
- 208000017520 skin disease Diseases 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 210000002435 tendon Anatomy 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
- 238000012360 testing method Methods 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 239000003104 tissue culture media Substances 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- 239000005051 trimethylchlorosilane Substances 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/01—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing oxygen
-
- 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
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US84433192A | 1992-03-02 | 1992-03-02 | |
| US84433192 | 1992-03-02 | ||
| US9300470 | 1993-01-28 | ||
| PCT/US1993/000470 WO1993018050A1 (en) | 1992-03-02 | 1993-01-28 | Sugar derivatives of macrolides |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI944017L FI944017L (fi) | 1994-09-01 |
| FI944017A0 FI944017A0 (fi) | 1994-09-01 |
| FI107535B true FI107535B (fi) | 2001-08-31 |
Family
ID=25292419
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI944017A FI107535B (fi) | 1992-03-02 | 1994-09-01 | Makrolidien sokerijohdannaiset |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US5747465A (de) |
| EP (1) | EP0629209B1 (de) |
| JP (1) | JP2563080B2 (de) |
| AT (1) | ATE153027T1 (de) |
| AU (1) | AU3586293A (de) |
| CA (1) | CA2131372C (de) |
| DE (1) | DE69310721T2 (de) |
| DK (1) | DK0629209T3 (de) |
| ES (1) | ES2102642T3 (de) |
| FI (1) | FI107535B (de) |
| GR (1) | GR3024048T3 (de) |
| IL (1) | IL104817A0 (de) |
| MX (1) | MX9301060A (de) |
| WO (1) | WO1993018050A1 (de) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AUPP584198A0 (en) | 1998-09-14 | 1998-10-08 | Fujisawa Pharmaceutical Co., Ltd. | New use |
| WO2006115509A2 (en) | 2004-06-24 | 2006-11-02 | Novartis Vaccines And Diagnostics Inc. | Small molecule immunopotentiators and assays for their detection |
| CA2584358A1 (en) | 2004-12-01 | 2006-06-08 | Teva Gyogyszergyar Zartkoeruen Mukoedo Reszvenytarsasag | Non-hygroscopic and powdery amorphous pimecrolimus |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1467383A (en) * | 1974-06-12 | 1977-03-16 | Farmaceutici Italia | Daunomycin analogues |
| US4894366A (en) * | 1984-12-03 | 1990-01-16 | Fujisawa Pharmaceutical Company, Ltd. | Tricyclo compounds, a process for their production and a pharmaceutical composition containing the same |
| JP2799208B2 (ja) * | 1987-12-09 | 1998-09-17 | フアイソンズ・ピーエルシー | マクロ環状化合物 |
| AU6286690A (en) * | 1989-08-18 | 1991-04-03 | Fisons Plc | Macrocyclic compounds |
| IE904050A1 (en) * | 1989-11-13 | 1991-05-22 | Merck & Co Inc | Aminomacrolides and derivatives having immunosuppressive¹activity |
| EP0466365A3 (en) * | 1990-07-03 | 1992-04-15 | Merck & Co. Inc. | Novel immunosuppressant fermentation products of a microorganism |
-
1993
- 1993-01-28 AT AT93904534T patent/ATE153027T1/de not_active IP Right Cessation
- 1993-01-28 DK DK93904534.0T patent/DK0629209T3/da active
- 1993-01-28 US US08/284,504 patent/US5747465A/en not_active Expired - Fee Related
- 1993-01-28 DE DE69310721T patent/DE69310721T2/de not_active Expired - Fee Related
- 1993-01-28 CA CA002131372A patent/CA2131372C/en not_active Expired - Fee Related
- 1993-01-28 EP EP93904534A patent/EP0629209B1/de not_active Expired - Lifetime
- 1993-01-28 WO PCT/US1993/000470 patent/WO1993018050A1/en not_active Ceased
- 1993-01-28 ES ES93904534T patent/ES2102642T3/es not_active Expired - Lifetime
- 1993-01-28 AU AU35862/93A patent/AU3586293A/en not_active Abandoned
- 1993-01-28 JP JP5515662A patent/JP2563080B2/ja not_active Expired - Fee Related
- 1993-02-22 IL IL104817A patent/IL104817A0/xx unknown
- 1993-02-26 MX MX9301060A patent/MX9301060A/es unknown
-
1994
- 1994-09-01 FI FI944017A patent/FI107535B/fi active
-
1997
- 1997-07-09 GR GR970401703T patent/GR3024048T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| MX9301060A (es) | 1993-09-01 |
| JP2563080B2 (ja) | 1996-12-11 |
| ATE153027T1 (de) | 1997-05-15 |
| GR3024048T3 (en) | 1997-10-31 |
| ES2102642T3 (es) | 1997-08-01 |
| JPH07500352A (ja) | 1995-01-12 |
| WO1993018050A1 (en) | 1993-09-16 |
| US5747465A (en) | 1998-05-05 |
| CA2131372A1 (en) | 1993-09-16 |
| EP0629209A1 (de) | 1994-12-21 |
| EP0629209B1 (de) | 1997-05-14 |
| FI944017L (fi) | 1994-09-01 |
| DE69310721D1 (de) | 1997-06-19 |
| FI944017A0 (fi) | 1994-09-01 |
| DE69310721T2 (de) | 1997-09-04 |
| IL104817A0 (en) | 1993-06-10 |
| DK0629209T3 (da) | 1997-10-13 |
| AU3586293A (en) | 1993-10-05 |
| CA2131372C (en) | 1998-07-14 |
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