JPH0516426B2 - - Google Patents
Info
- Publication number
- JPH0516426B2 JPH0516426B2 JP59127698A JP12769884A JPH0516426B2 JP H0516426 B2 JPH0516426 B2 JP H0516426B2 JP 59127698 A JP59127698 A JP 59127698A JP 12769884 A JP12769884 A JP 12769884A JP H0516426 B2 JPH0516426 B2 JP H0516426B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- compound
- valeryloxy
- hydroxy
- hexyl
- 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
Links
- 150000001875 compounds Chemical class 0.000 claims abstract description 40
- 244000005700 microbiome Species 0.000 claims abstract description 6
- 238000000034 method Methods 0.000 claims description 11
- 108050006759 Pancreatic lipases Proteins 0.000 claims description 10
- 102000019280 Pancreatic lipases Human genes 0.000 claims description 10
- 229940116369 pancreatic lipase Drugs 0.000 claims description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- 241000187747 Streptomyces Species 0.000 claims description 8
- 239000013543 active substance Substances 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 8
- -1 (2S,3S,5S)-5-[(S)-2-formamido-4-methyl-valeryloxy]-2-hexyl-3-hydroxy-hexadecanoic acid lactone Chemical class 0.000 claims description 6
- 230000002401 inhibitory effect Effects 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 241000894007 species Species 0.000 claims description 4
- 239000001963 growth medium Substances 0.000 claims description 2
- 239000003112 inhibitor Substances 0.000 claims 1
- 241000946767 Streptomyces toxytricini Species 0.000 abstract description 5
- 208000031226 Hyperlipidaemia Diseases 0.000 abstract description 3
- 108090001060 Lipase Proteins 0.000 abstract description 3
- 239000004367 Lipase Substances 0.000 abstract description 3
- 102000004882 Lipase Human genes 0.000 abstract description 3
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- 235000019421 lipase Nutrition 0.000 abstract description 3
- 235000020824 obesity Nutrition 0.000 abstract description 3
- 230000002265 prevention Effects 0.000 abstract description 3
- 210000000496 pancreas Anatomy 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 21
- 238000000855 fermentation Methods 0.000 description 19
- 230000004151 fermentation Effects 0.000 description 19
- SIKWOTFNWURSAY-UHFFFAOYSA-N Lipstatin Natural products CCCCCCC1C(CC(CC=CCC=CCCCCC)C(=O)OC(CC(C)C)NC=O)OC1=O SIKWOTFNWURSAY-UHFFFAOYSA-N 0.000 description 18
- OQMAKWGYQLJJIA-CUOOPAIESA-N lipstatin Chemical compound CCCCCC[C@H]1[C@H](C[C@H](C\C=C/C\C=C/CCCCC)OC(=O)[C@H](CC(C)C)NC=O)OC1=O OQMAKWGYQLJJIA-CUOOPAIESA-N 0.000 description 17
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 229920001817 Agar Polymers 0.000 description 11
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- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000005273 aeration Methods 0.000 description 6
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- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- 239000005642 Oleic acid Substances 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
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- 238000010521 absorption reaction Methods 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
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- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 4
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- 229910002027 silica gel Inorganic materials 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 150000003626 triacylglycerols Chemical class 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 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 3
- AHLBNYSZXLDEJQ-UHFFFAOYSA-N N-formyl-L-leucylester Natural products CCCCCCCCCCCC(OC(=O)C(CC(C)C)NC=O)CC1OC(=O)C1CCCCCC AHLBNYSZXLDEJQ-UHFFFAOYSA-N 0.000 description 3
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- 239000008103 glucose Substances 0.000 description 3
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- 229960001243 orlistat Drugs 0.000 description 3
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- 239000004455 soybean meal Substances 0.000 description 3
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- 235000019698 starch Nutrition 0.000 description 3
- UQZSVIGPZAULMV-DKWTVANSSA-N (2s)-2,4-diamino-4-oxobutanoic acid;propane-1,2,3-triol Chemical compound OCC(O)CO.OC(=O)[C@@H](N)CC(N)=O UQZSVIGPZAULMV-DKWTVANSSA-N 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 2
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 2
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 2
- HMFHBZSHGGEWLO-SOOFDHNKSA-N D-ribofuranose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H]1O HMFHBZSHGGEWLO-SOOFDHNKSA-N 0.000 description 2
- SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical compound O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 description 2
- 229920001353 Dextrin Polymers 0.000 description 2
- 239000004375 Dextrin Substances 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 101710158368 Extracellular lipase Proteins 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 2
- 239000001888 Peptone Substances 0.000 description 2
- 108010080698 Peptones Proteins 0.000 description 2
- PYMYPHUHKUWMLA-LMVFSUKVSA-N Ribose Natural products OC[C@@H](O)[C@@H](O)[C@@H](O)C=O PYMYPHUHKUWMLA-LMVFSUKVSA-N 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
- 101710128940 Triacylglycerol lipase Proteins 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- BAECOWNUKCLBPZ-HIUWNOOHSA-N Triolein Natural products O([C@H](OCC(=O)CCCCCCC/C=C\CCCCCCCC)COC(=O)CCCCCCC/C=C\CCCCCCCC)C(=O)CCCCCCC/C=C\CCCCCCCC BAECOWNUKCLBPZ-HIUWNOOHSA-N 0.000 description 2
- PHYFQTYBJUILEZ-UHFFFAOYSA-N Trioleoylglycerol Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC(OC(=O)CCCCCCCC=CCCCCCCCC)COC(=O)CCCCCCCC=CCCCCCCCC PHYFQTYBJUILEZ-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- HMFHBZSHGGEWLO-UHFFFAOYSA-N alpha-D-Furanose-Ribose Natural products OCC1OC(O)C(O)C1O HMFHBZSHGGEWLO-UHFFFAOYSA-N 0.000 description 2
- PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 description 2
- 238000003556 assay Methods 0.000 description 2
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 description 2
- 229940041514 candida albicans extract Drugs 0.000 description 2
- 238000000451 chemical ionisation Methods 0.000 description 2
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- 239000003153 chemical reaction reagent Substances 0.000 description 2
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
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- 235000011187 glycerol Nutrition 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
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- 238000002329 infrared spectrum Methods 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 2
- 229940040461 lipase Drugs 0.000 description 2
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- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
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- AHLBNYSZXLDEJQ-FWEHEUNISA-N orlistat Chemical compound CCCCCCCCCCC[C@H](OC(=O)[C@H](CC(C)C)NC=O)C[C@@H]1OC(=O)[C@H]1CCCCCC AHLBNYSZXLDEJQ-FWEHEUNISA-N 0.000 description 2
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- CDAISMWEOUEBRE-UHFFFAOYSA-N scyllo-inosotol Natural products OC1C(O)C(O)C(O)C(O)C1O CDAISMWEOUEBRE-UHFFFAOYSA-N 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000010902 straw Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- AWDRATDZQPNJFN-VAYUFCLWSA-N taurodeoxycholic acid Chemical compound C([C@H]1CC2)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(=O)NCCS(O)(=O)=O)C)[C@@]2(C)[C@@H](O)C1 AWDRATDZQPNJFN-VAYUFCLWSA-N 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
- C12N1/00—Microorganisms, e.g. protozoa; Compositions thereof; Processes of propagating, maintaining or preserving microorganisms or compositions thereof; Processes of preparing or isolating a composition containing a microorganism; Culture media therefor
- C12N1/20—Bacteria; Culture media therefor
- C12N1/205—Bacterial isolates
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P13/00—Preparation of nitrogen-containing organic compounds
- C12P13/04—Alpha- or beta- amino acids
- C12P13/06—Alanine; Leucine; Isoleucine; Serine; Homoserine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D305/00—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms
- C07D305/02—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D305/10—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms not condensed with other rings having one or more double bonds between ring members or between ring members and non-ring members
- C07D305/12—Beta-lactones
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
- C12P17/02—Oxygen as only ring hetero atoms
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12R—INDEXING SCHEME ASSOCIATED WITH SUBCLASSES C12C - C12Q, RELATING TO MICROORGANISMS
- C12R2001/00—Microorganisms ; Processes using microorganisms
- C12R2001/01—Bacteria or Actinomycetales ; using bacteria or Actinomycetales
- C12R2001/465—Streptomyces
-
- 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
- Y10S435/00—Chemistry: molecular biology and microbiology
- Y10S435/8215—Microorganisms
- Y10S435/822—Microorganisms using bacteria or actinomycetales
- Y10S435/886—Streptomyces
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Biotechnology (AREA)
- General Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Microbiology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Tropical Medicine & Parasitology (AREA)
- Virology (AREA)
- Biomedical Technology (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Obesity (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Saccharide Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Epoxy Compounds (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Micro-Organisms Or Cultivation Processes Thereof (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH3415/83-4 | 1983-06-22 | ||
| CH341583 | 1983-06-22 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6013777A JPS6013777A (ja) | 1985-01-24 |
| JPH0516426B2 true JPH0516426B2 (enExample) | 1993-03-04 |
Family
ID=4255488
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59127698A Granted JPS6013777A (ja) | 1983-06-22 | 1984-06-22 | 新規化合物 |
Country Status (26)
| Country | Link |
|---|---|
| US (1) | US4598089A (enExample) |
| EP (1) | EP0129748B1 (enExample) |
| JP (1) | JPS6013777A (enExample) |
| KR (1) | KR920002314B1 (enExample) |
| AT (1) | ATE30025T1 (enExample) |
| AU (1) | AU572851B2 (enExample) |
| BG (1) | BG60766B2 (enExample) |
| CA (1) | CA1247547A (enExample) |
| DE (2) | DE19875045I2 (enExample) |
| DK (1) | DK160496C (enExample) |
| ES (1) | ES533557A0 (enExample) |
| FI (1) | FI78694C (enExample) |
| GR (1) | GR82120B (enExample) |
| HU (1) | HU193579B (enExample) |
| IE (1) | IE57761B1 (enExample) |
| IL (1) | IL72122A (enExample) |
| LU (1) | LU90302I2 (enExample) |
| LV (1) | LV5747B4 (enExample) |
| MC (1) | MC1602A1 (enExample) |
| MX (1) | MX9203633A (enExample) |
| NL (1) | NL980029I2 (enExample) |
| NO (2) | NO159941C (enExample) |
| NZ (1) | NZ208521A (enExample) |
| PH (1) | PH19704A (enExample) |
| PT (1) | PT78777B (enExample) |
| ZA (1) | ZA844558B (enExample) |
Families Citing this family (234)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1270837A (en) * | 1984-12-21 | 1990-06-26 | Hoffmann-La Roche Limited | Oxetanones |
| CA1328881C (en) * | 1984-12-21 | 1994-04-26 | Pierre Barbier | Process for the manufacture of oxetanones |
| ZA859574B (en) * | 1984-12-21 | 1986-08-27 | Hoffmann La Roche | Process for the manufacture of oxetanones |
| JPH0618793Y2 (ja) * | 1986-06-13 | 1994-05-18 | パイオニア株式会社 | 作業台 |
| US4806564A (en) * | 1987-05-26 | 1989-02-21 | Merck & Co., Inc. | Antihypercholesterolemic beta-lactones |
| US4816477A (en) * | 1987-05-26 | 1989-03-28 | Merck & Co., Inc. | Antihypercholesterolemic β-lactones |
| US5484777A (en) * | 1989-04-20 | 1996-01-16 | Lange, Iii; Louis G. | Pancreatic cholesterol esterase inhibitor |
| US5017565A (en) * | 1989-04-20 | 1991-05-21 | Lange Iii Louis G | Use of sulfated polysaccharides to inhibit pancreatic cholesterol esterase |
| US5063210A (en) * | 1989-04-20 | 1991-11-05 | Lange Iii Louis G | Use of sulfated polysaccharides to decrease cholesterol and fatty acid absorption |
| US5376640A (en) * | 1989-12-25 | 1994-12-27 | Nisshin Flour Milling Co., Ltd. | Lipolytic enzyme inhibitors |
| JP2960947B2 (ja) * | 1989-12-25 | 1999-10-12 | 日清製粉株式会社 | 脂質分解酵素阻害剤 |
| CA2098167C (en) * | 1992-06-24 | 2006-12-19 | Dorothea Isler | Foodstuffs and feedstuffs containing a lipase inhibitor |
| TW381025B (en) * | 1993-08-05 | 2000-02-01 | Hoffmann La Roche | Pharmaceutical composition containing a glucosidase inhibitor and a lipase inhibitor |
| US6642268B2 (en) | 1994-09-13 | 2003-11-04 | G.D. Searle & Co. | Combination therapy employing ileal bile acid transport inhibiting benzothipines and HMG Co-A reductase inhibitors |
| US6262277B1 (en) | 1994-09-13 | 2001-07-17 | G.D. Searle And Company | Intermediates and processes for the preparation of benzothiepines having activity as inhibitors of ileal bile acid transport and taurocholate uptake |
| US6268392B1 (en) | 1994-09-13 | 2001-07-31 | G. D. Searle & Co. | Combination therapy employing ileal bile acid transport inhibiting benzothiepines and HMG Co-A reductase inhibitors |
| MY116591A (en) * | 1996-04-26 | 2004-02-28 | Hoffmann La Roche | Process for the production of lipstatin and tetrahydrolipstatin |
| PL191222B1 (pl) * | 1997-02-05 | 2006-03-31 | Hoffmann La Roche | Zastosowanie tetrahydrolipstatyny do wytwarzania doustnego farmaceutycznego preparatu do leczenia cukrzycy typu II |
| US6004996A (en) * | 1997-02-05 | 1999-12-21 | Hoffman-La Roche Inc. | Tetrahydrolipstatin containing compositions |
| US7344713B1 (en) * | 1997-07-07 | 2008-03-18 | Pimentel Julio L | Decreased fat absorption with an anti-lipase antibody |
| RU2234917C2 (ru) * | 1997-12-24 | 2004-08-27 | Кнолль Акциенгезелльшафт | Терапевтические средства |
| GB9727131D0 (en) * | 1997-12-24 | 1998-02-25 | Knoll Ag | Therapeutic agents |
| US6264937B1 (en) | 1998-01-09 | 2001-07-24 | Geltex Pharmaceuticals, Inc. | Fat-binding polymers |
| US6299868B1 (en) | 1999-07-14 | 2001-10-09 | Geltex Pharmaceuticals, Inc. | Fat-binding polymers |
| US7048917B1 (en) | 1998-01-09 | 2006-05-23 | Genzyme Corporation | Fat-binding polymers |
| AU761351B2 (en) | 1998-08-14 | 2003-06-05 | Cheplapharm Arzneimittel Gmbh | Pharmaceutical compositions containing lipase inhibitors |
| ATE263558T1 (de) * | 1998-08-14 | 2004-04-15 | Hoffmann La Roche | Lipasehemmer und chitosan enthaltende pharmazeutische zusammensetzungen |
| CA2356422C (en) | 1998-12-23 | 2008-09-16 | G.D. Searle Llc | Combinations of ileal bile acid transport inhibitors and cholesteryl ester transfer protein inhibitors for cardiovascular indications |
| HUP0104745A3 (en) | 1998-12-23 | 2003-01-28 | G D Searle Llc Chicago | Combinations of ileal bile acid transport inhibitors and bile acid sequestring agents for cardiovascular indications |
| US6462091B1 (en) | 1998-12-23 | 2002-10-08 | G.D. Searle & Co. | Combinations of cholesteryl ester transfer protein inhibitors and HMG coA reductase inhibitors for cardiovascular indications |
| AU2157500A (en) | 1998-12-23 | 2000-07-31 | G.D. Searle Llc | Combinations of cholesteryl ester transfer protein inhibitors and bile acid sequestering agents for cardiovascular indications |
| ATE242007T1 (de) | 1998-12-23 | 2003-06-15 | Searle Llc | Kombinationen von cholesteryl ester transfer protein inhibitoren und nicotinsäure derivaten für kardiovaskuläre indikationen |
| CZ20012342A3 (cs) | 1998-12-23 | 2001-12-12 | G. D. Searle Llc | Kombinace inhibitorů transportu ľlučové kyseliny v ileu a derivátů kyseliny fibrové pro kardiovaskulární indikace |
| ES2201827T3 (es) | 1998-12-23 | 2004-03-16 | G.D. Searle Llc | Combinaciones de inhibidores de la proteina de transferencia de ester de colesterilo y de derivados de acido fibrico para indicaciones cardiovasculares. |
| ES2185523T3 (es) * | 1999-01-29 | 2003-05-01 | Hoffmann La Roche | Purificacion de lipstatina. |
| CA2379308A1 (en) * | 1999-07-14 | 2001-01-25 | Geltex Pharmaceuticals, Inc. | Fat-binding polymers, optionally combined with lipase inhibitors |
| AR025587A1 (es) * | 1999-09-13 | 2002-12-04 | Hoffmann La Roche | Formulaciones en dispersion que contienen inhibidores de lipasa |
| AR025609A1 (es) * | 1999-09-13 | 2002-12-04 | Hoffmann La Roche | Formulaciones lipidas solidas |
| EP1132389A1 (en) | 2000-03-06 | 2001-09-12 | Vernalis Research Limited | New aza-indolyl derivatives for the treatment of obesity |
| WO2001068637A2 (en) | 2000-03-10 | 2001-09-20 | Pharmacia Corporation | Method for the preparation of tetrahydrobenzothiepines |
| EP1142572A1 (de) * | 2000-04-04 | 2001-10-10 | Volker Dr. Helmstädter | Oxetanon-enthaltende Präparate zur Behandlung von Darmerkrankungen |
| DE10021618A1 (de) * | 2000-05-04 | 2001-11-15 | Volker Helmstaedter | Präparat für Darmerkrankungen und dessen Verwendung |
| WO2002000201A2 (en) * | 2000-06-27 | 2002-01-03 | F. Hoffmann-La Roche Ag | Method for preparing a composition |
| PT1307264E (pt) * | 2000-07-28 | 2005-02-28 | Hoffmann La Roche | Nova composicao farmaceutica |
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| GB0106177D0 (en) * | 2001-03-13 | 2001-05-02 | Hoffmann La Roche | Piperazine derivatives |
| US20030091610A1 (en) * | 2001-03-19 | 2003-05-15 | The Procter & Gamble Company | Use of non-digestible polymeric foams to sequester ingested materials thereby inhibiting their absorption by the body |
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| US8900498B2 (en) | 2001-10-12 | 2014-12-02 | Monosol Rx, Llc | Process for manufacturing a resulting multi-layer pharmaceutical film |
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| US20230338387A1 (en) | 2020-02-05 | 2023-10-26 | Nof Corporation | Agent For Treating Or Preventing Pancreatic Fistula |
| EP4422607A4 (en) | 2021-10-25 | 2025-09-03 | Aquestive Therapeutics Inc | ORAL AND NASAL COMPOSITIONS AND METHODS OF TREATMENT |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS608117B2 (ja) * | 1977-02-08 | 1985-02-28 | 財団法人微生物化学研究会 | 新生理活性物質エステラスチンおよびその製造法 |
| GB2023604B (en) * | 1978-05-25 | 1982-07-28 | Microbial Chem Res Found | Physiologically active derivatives of esterastin and production thereof |
| JPS56128774A (en) * | 1980-03-14 | 1981-10-08 | Microbial Chem Res Found | New physiologically active substance ebelactone and its preparation |
| CA1328881C (en) * | 1984-12-21 | 1994-04-26 | Pierre Barbier | Process for the manufacture of oxetanones |
-
1984
- 1984-05-25 CA CA000455089A patent/CA1247547A/en not_active Expired
- 1984-06-05 AT AT84106420T patent/ATE30025T1/de active
- 1984-06-05 DE DE1998175045 patent/DE19875045I2/de active Active
- 1984-06-05 DE DE8484106420T patent/DE3466538D1/de not_active Expired
- 1984-06-05 EP EP84106420A patent/EP0129748B1/de not_active Expired
- 1984-06-14 FI FI842422A patent/FI78694C/fi not_active IP Right Cessation
- 1984-06-15 IL IL72122A patent/IL72122A/xx not_active IP Right Cessation
- 1984-06-15 NZ NZ208521A patent/NZ208521A/en unknown
- 1984-06-15 ZA ZA844558A patent/ZA844558B/xx unknown
- 1984-06-18 US US06/621,827 patent/US4598089A/en not_active Expired - Lifetime
- 1984-06-18 AU AU29478/84A patent/AU572851B2/en not_active Expired
- 1984-06-20 PT PT78777A patent/PT78777B/pt unknown
- 1984-06-20 HU HU842372A patent/HU193579B/hu unknown
- 1984-06-20 GR GR75059A patent/GR82120B/el unknown
- 1984-06-20 MC MC841710A patent/MC1602A1/fr unknown
- 1984-06-20 ES ES533557A patent/ES533557A0/es active Granted
- 1984-06-21 NO NO842512A patent/NO159941C/no not_active IP Right Cessation
- 1984-06-21 KR KR1019840003509A patent/KR920002314B1/ko not_active Expired
- 1984-06-21 PH PH30863A patent/PH19704A/en unknown
- 1984-06-21 IE IE1566/84A patent/IE57761B1/en not_active IP Right Cessation
- 1984-06-22 DK DK308584A patent/DK160496C/da not_active IP Right Cessation
- 1984-06-22 JP JP59127698A patent/JPS6013777A/ja active Granted
-
1992
- 1992-06-26 MX MX9203633A patent/MX9203633A/es unknown
-
1994
- 1994-02-21 BG BG098503A patent/BG60766B2/bg unknown
-
1996
- 1996-05-24 LV LV960154A patent/LV5747B4/xx unknown
-
1998
- 1998-10-21 LU LU90302C patent/LU90302I2/fr unknown
- 1998-10-26 NL NL980029C patent/NL980029I2/nl unknown
-
2000
- 2000-05-31 NO NO2000003C patent/NO2000003I1/no unknown
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