CS262425B2 - Process for preparing new derivatives of 4-/2-hydroxyethyl/-2-oxetanes - Google Patents

Process for preparing new derivatives of 4-/2-hydroxyethyl/-2-oxetanes Download PDF

Info

Publication number: CS262425B2
Authority: CS; Czechoslovakia
Prior art keywords: group; pyran; tetrahydro; hexyl; formula
Prior art date: 1984-12-21

Application number

CS859016A

Other languages

Czech (cs)

English (en)

Inventor

Pierre Dr Barbier

Fernand Dr Schneider

Ulrich Dr Widmer

Original Assignee

Hoffmann La Roche

Priority date (The priority date 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 date listed.)

1984-12-21

Filing date

1985-12-09

Publication date

1989-03-14

1985-12-09 Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche

1989-03-14 Publication of CS262425B2 publication Critical patent/CS262425B2/cs

Links

125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 title claims description 4
238000004519 manufacturing process Methods 0.000 title description 15
-1 2,5-undecadienyl group Chemical group 0.000 claims description 163
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 93
239000007858 starting material Substances 0.000 claims description 69
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 42
150000001875 compounds Chemical class 0.000 claims description 41
239000002253 acid Substances 0.000 claims description 36
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 22
238000006243 chemical reaction Methods 0.000 claims description 22
125000004432 carbon atom Chemical group C* 0.000 claims description 20
239000001257 hydrogen Substances 0.000 claims description 19
229910052739 hydrogen Inorganic materials 0.000 claims description 19
238000000034 method Methods 0.000 claims description 17
150000007513 acids Chemical class 0.000 claims description 15
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
238000002360 preparation method Methods 0.000 claims description 15
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
150000003839 salts Chemical class 0.000 claims description 11
125000000217 alkyl group Chemical group 0.000 claims description 10
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 10
VEZXCJBBBCKRPI-UHFFFAOYSA-N beta-propiolactone Chemical group O=C1CCO1 VEZXCJBBBCKRPI-UHFFFAOYSA-N 0.000 claims description 10
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125000001424 substituent group Chemical group 0.000 claims description 8
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125000002960 margaryl group Chemical group [H]C([*])([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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
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150000001350 alkyl halides Chemical class 0.000 description 1
BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
235000019270 ammonium chloride Nutrition 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
239000003963 antioxidant agent Substances 0.000 description 1
235000006708 antioxidants Nutrition 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
239000012300 argon atmosphere Substances 0.000 description 1
239000011668 ascorbic acid Substances 0.000 description 1
235000010323 ascorbic acid Nutrition 0.000 description 1
229960005070 ascorbic acid Drugs 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
239000002585 base Substances 0.000 description 1
229940116226 behenic acid Drugs 0.000 description 1
YPDPKOLRRHVBNL-LIMHNSPMSA-N benzyl (2s,3s,5r)-3-[tert-butyl(dimethyl)silyl]oxy-2-hexyl-5-(oxan-2-yloxy)hexadecanoate Chemical compound O=C([C@@H](CCCCCC)[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@H](CCCCCCCCCCC)OC1OCCCC1)OCC1=CC=CC=C1 YPDPKOLRRHVBNL-LIMHNSPMSA-N 0.000 description 1
WLTYLNJVIIEJLA-CEUYOYMZSA-N benzyl (2s,3s,5r)-3-[tert-butyl(dimethyl)silyl]oxy-2-hexyl-5-hydroxyhexadecanoate Chemical compound CCCCCCCCCCC[C@@H](O)C[C@H](O[Si](C)(C)C(C)(C)C)[C@H](CCCCCC)C(=O)OCC1=CC=CC=C1 WLTYLNJVIIEJLA-CEUYOYMZSA-N 0.000 description 1
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 1
230000037396 body weight Effects 0.000 description 1
239000012267 brine Substances 0.000 description 1
239000000872 buffer Substances 0.000 description 1
235000014121 butter Nutrition 0.000 description 1
QPQYEVGNYFEEFX-BJYSPHJKSA-N butyl (3R)-3-hydroxy-5-(oxan-2-yloxy)hexadecanoate Chemical compound O[C@@H](CC(=O)OCCCC)CC(CCCCCCCCCCC)OC1OCCCC1 QPQYEVGNYFEEFX-BJYSPHJKSA-N 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000011575 calcium Substances 0.000 description 1
239000001110 calcium chloride Substances 0.000 description 1
229910001628 calcium chloride Inorganic materials 0.000 description 1
235000019219 chocolate Nutrition 0.000 description 1
235000012000 cholesterol Nutrition 0.000 description 1
229930016911 cinnamic acid Natural products 0.000 description 1
235000013985 cinnamic acid Nutrition 0.000 description 1
229940117916 cinnamic aldehyde Drugs 0.000 description 1
239000011248 coating agent Substances 0.000 description 1
239000003086 colorant Substances 0.000 description 1
235000009508 confectionery Nutrition 0.000 description 1
239000000470 constituent Substances 0.000 description 1
239000008120 corn starch Substances 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
RNOJZAYWQCKGRK-UHFFFAOYSA-N diazene hydrochloride Chemical compound Cl.N=N RNOJZAYWQCKGRK-UHFFFAOYSA-N 0.000 description 1
FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 1
230000006806 disease prevention Effects 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
CVCXSNONTRFSEH-UHFFFAOYSA-N docosa-2,4-dienoic acid Chemical compound CCCCCCCCCCCCCCCCCC=CC=CC(O)=O CVCXSNONTRFSEH-UHFFFAOYSA-N 0.000 description 1
KFEVDPWXEVUUMW-UHFFFAOYSA-N docosanoic acid Natural products CCCCCCCCCCCCCCCCCCCCCC(=O)OCCC1=CC=C(O)C=C1 KFEVDPWXEVUUMW-UHFFFAOYSA-N 0.000 description 1
125000003438 dodecyl group Chemical group [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])* 0.000 description 1
229940079593 drug Drugs 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000008344 egg yolk phospholipid Substances 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
ZKQFHRVKCYFVCN-UHFFFAOYSA-N ethoxyethane;hexane Chemical compound CCOCC.CCCCCC ZKQFHRVKCYFVCN-UHFFFAOYSA-N 0.000 description 1
ORDGRJBWPGCHAO-PUODRLBUSA-N ethyl (4r)-4-(oxan-2-yloxy)-7-oxoheptanoate Chemical compound CCOC(=O)CC[C@@H](CCC=O)OC1CCCCO1 ORDGRJBWPGCHAO-PUODRLBUSA-N 0.000 description 1
FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 description 1
239000000284 extract Substances 0.000 description 1
201000005577 familial hyperlipidemia Diseases 0.000 description 1
239000012065 filter cake Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
239000011888 foil Substances 0.000 description 1
235000013355 food flavoring agent Nutrition 0.000 description 1
235000003599 food sweetener Nutrition 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
235000011087 fumaric acid Nutrition 0.000 description 1
239000008103 glucose Substances 0.000 description 1
125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
230000006698 induction Effects 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
229960004903 invert sugar Drugs 0.000 description 1
QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
239000008101 lactose Substances 0.000 description 1
235000019626 lipase activity Nutrition 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
UKZCGMDMXDLAGZ-UHFFFAOYSA-M magnesium;2-methylpropane;bromide Chemical compound [Mg+2].[Br-].C[C-](C)C UKZCGMDMXDLAGZ-UHFFFAOYSA-M 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
239000001630 malic acid Substances 0.000 description 1
235000011090 malic acid Nutrition 0.000 description 1
235000013310 margarine Nutrition 0.000 description 1
239000003264 margarine Substances 0.000 description 1
229910052987 metal hydride Inorganic materials 0.000 description 1
150000004681 metal hydrides Chemical class 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
SCDGDIOOASKSME-QNKVVAGZSA-N methyl (2s,3s,5s)-2-ethyl-3-hydroxy-5-(oxan-2-yloxy)docosanoate Chemical compound CCCCCCCCCCCCCCCCC[C@@H](C[C@H](O)[C@H](CC)C(=O)OC)OC1CCCCO1 SCDGDIOOASKSME-QNKVVAGZSA-N 0.000 description 1
AZGKXHRTSVLLTI-JTDNENJMSA-N methyl (3r)-3-(oxan-2-yloxy)hept-6-enoate Chemical compound COC(=O)C[C@@H](CCC=C)OC1CCCCO1 AZGKXHRTSVLLTI-JTDNENJMSA-N 0.000 description 1
NLOBFGOFYTWAIQ-JTDNENJMSA-N methyl (4r)-4-(oxan-2-yloxy)-7-oxoheptanoate Chemical compound COC(=O)CC[C@@H](CCC=O)OC1CCCCO1 NLOBFGOFYTWAIQ-JTDNENJMSA-N 0.000 description 1
IBUNOEXEHUNASK-PISNEZEASA-N methyl (z,3s)-3-hydroxyicos-11-enoate Chemical compound CCCCCCCC\C=C/CCCCCCC[C@H](O)CC(=O)OC IBUNOEXEHUNASK-PISNEZEASA-N 0.000 description 1
QLKIRIJPLOZMMY-DJUCYVQHSA-N methyl (z,3s,5s)-3-hydroxy-5-(oxan-2-yloxy)docos-13-enoate Chemical compound CCCCCCCC\C=C/CCCCCCC[C@@H](C[C@H](O)CC(=O)OC)OC1CCCCO1 QLKIRIJPLOZMMY-DJUCYVQHSA-N 0.000 description 1
HBVHDPSYAJZFEF-UHFFFAOYSA-N methyl 2-acetyloctanoate Chemical compound CCCCCCC(C(C)=O)C(=O)OC HBVHDPSYAJZFEF-UHFFFAOYSA-N 0.000 description 1
HVVZNBBKHPHBRW-UHFFFAOYSA-N methyl 2-hexyl-3-hydroxy-5-(oxan-2-yloxy)hexadecanoate Chemical compound CCCCCCCCCCCC(CC(O)C(CCCCCC)C(=O)OC)OC1CCCCO1 HVVZNBBKHPHBRW-UHFFFAOYSA-N 0.000 description 1
RYBPPYGMJPYBFL-UHFFFAOYSA-N methyl 2-hexyl-5-(oxan-2-yloxy)-3-oxohexadecanoate Chemical compound CCCCCCCCCCCC(CC(=O)C(CCCCCC)C(=O)OC)OC1CCCCO1 RYBPPYGMJPYBFL-UHFFFAOYSA-N 0.000 description 1
LCYXCWLJSOHFFX-UHFFFAOYSA-N methyl 2-hexyl-5-hydroxy-3-oxohexadecanoate Chemical compound CCCCCCCCCCCC(O)CC(=O)C(C(=O)OC)CCCCCC LCYXCWLJSOHFFX-UHFFFAOYSA-N 0.000 description 1
JMANFENOVOAFTJ-UHFFFAOYSA-N methyl 3-(oxan-2-yloxy)tetradecanoate Chemical compound CCCCCCCCCCCC(CC(=O)OC)OC1CCCCO1 JMANFENOVOAFTJ-UHFFFAOYSA-N 0.000 description 1
UOZZAMWODZQSOA-UHFFFAOYSA-N methyl 3-hydroxytetradecanoate Chemical compound CCCCCCCCCCCC(O)CC(=O)OC UOZZAMWODZQSOA-UHFFFAOYSA-N 0.000 description 1
WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
238000002156 mixing Methods 0.000 description 1
125000000896 monocarboxylic acid group Chemical group 0.000 description 1
125000001196 nonadecyl group Chemical group [H]C([*])([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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
230000003204 osmotic effect Effects 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
238000005949 ozonolysis reaction Methods 0.000 description 1
125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
HVAMZGADVCBITI-UHFFFAOYSA-N pent-4-enoic acid Chemical compound OC(=O)CCC=C HVAMZGADVCBITI-UHFFFAOYSA-N 0.000 description 1
125000003884 phenylalkyl group Chemical group 0.000 description 1
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
MERGMNQXULKBCH-UHFFFAOYSA-N pyran-2,4-dione Chemical compound O=C1CC(=O)C=CO1 MERGMNQXULKBCH-UHFFFAOYSA-N 0.000 description 1
125000000719 pyrrolidinyl group Chemical group 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
230000002829 reductive effect Effects 0.000 description 1
238000010992 reflux Methods 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
230000000630 rising effect Effects 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
239000000758 substrate Substances 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
125000003375 sulfoxide group Chemical group 0.000 description 1
230000001629 suppression Effects 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
WBWWGRHZICKQGZ-HZAMXZRMSA-N taurocholic acid Chemical compound C([C@H]1C[C@H]2O)[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 WBWWGRHZICKQGZ-HZAMXZRMSA-N 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
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
RGRAUZKPLRNLEB-UTJQPWESSA-N tert-butyl (11z,14z)-3-(oxan-2-yloxy)icosa-11,14-dienoate Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(CC(=O)OC(C)(C)C)OC1CCCCO1 RGRAUZKPLRNLEB-UTJQPWESSA-N 0.000 description 1
GYZMWQRWLVRBEL-UTJQPWESSA-N tert-butyl (13z,16z)-2-benzyl-3-hydroxy-5-(oxan-2-yloxy)docosa-13,16-dienoate Chemical compound C1CCCOC1OC(CCCCCCC\C=C/C\C=C/CCCCC)CC(O)C(C(=O)OC(C)(C)C)CC1=CC=CC=C1 GYZMWQRWLVRBEL-UTJQPWESSA-N 0.000 description 1
XXWVSMYCVRDJOO-PSDZMVHGSA-N tert-butyl (3r)-3-(oxan-2-yloxy)tetradecanoate Chemical compound CCCCCCCCCCC[C@H](CC(=O)OC(C)(C)C)OC1CCCCO1 XXWVSMYCVRDJOO-PSDZMVHGSA-N 0.000 description 1
YYZKKCVNAPQHEP-OTDUKCBNSA-N tert-butyl (z,3r)-3-hydroxyicos-11-enoate Chemical compound CCCCCCCC\C=C/CCCCCCC[C@@H](O)CC(=O)OC(C)(C)C YYZKKCVNAPQHEP-OTDUKCBNSA-N 0.000 description 1
SCSLUABEVMLYEA-UHFFFAOYSA-N tert-butyl pentanoate Chemical compound CCCCC(=O)OC(C)(C)C SCSLUABEVMLYEA-UHFFFAOYSA-N 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000001993 wax Substances 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
- 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
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D309/10—Oxygen atoms
- C07D309/12—Oxygen atoms only hydrogen atoms and one oxygen atom directly attached to ring carbon atoms, e.g. tetrahydropyranyl ethers
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/16—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D309/28—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D309/30—Oxygen atoms, e.g. delta-lactones
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Epoxy Compounds (AREA)
Polyesters Or Polycarbonates (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

CS859016A 1984-12-21 1985-12-09 Process for preparing new derivatives of 4-/2-hydroxyethyl/-2-oxetanes CS262425B2 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
CH610284		1984-12-21
CH393485		1985-09-12

Publications (1)

Publication Number	Publication Date
CS262425B2 true CS262425B2 (en)	1989-03-14

Family

ID=25694219

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS859016A CS262425B2 (en)	1984-12-21	1985-12-09	Process for preparing new derivatives of 4-/2-hydroxyethyl/-2-oxetanes

Country Status (20)

Country	Link
US (2)	US4931463A (fr)
EP (1)	EP0185359B1 (fr)
CN (1)	CN1012643B (fr)
AT (1)	ATE70061T1 (fr)
AU (1)	AU583569B2 (fr)
CA (1)	CA1270837A (fr)
CS (1)	CS262425B2 (fr)
DE (1)	DE3584829D1 (fr)
DK (1)	DK166724B1 (fr)
DO (1)	DOP1985004386A (fr)
FI (1)	FI91403C (fr)
HU (1)	HU200172B (fr)
IE (1)	IE58926B1 (fr)
IL (1)	IL77338A (fr)
MC (1)	MC1728A1 (fr)
NO (1)	NO171160C (fr)
NZ (1)	NZ214565A (fr)
PH (1)	PH26291A (fr)
PT (1)	PT81748B (fr)
ZW (1)	ZW20385A1 (fr)

Families Citing this family (68)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5246960A (en) *	1984-12-21	1993-09-21	Hoffmann-La Roche Inc.	Oxetanones
CA1328881C (fr) *	1984-12-21	1994-04-26	Pierre Barbier	Procede pour la fabrication d'oxetanones
US4895973A (en) *	1986-08-14	1990-01-23	G. D. Searle & Company	Substituted glutaric acid lactones in the treatment of hyperlipidemia
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
CA2035972C (fr) *	1990-02-23	2006-07-11	Martin Karpf	Procede de preparation d'oxetanones
US5260310A (en) *	1990-02-26	1993-11-09	Hoffmann-La Roche Inc.	Oxetanone compounds and pharmaceutical compositions containing them
CA2098167C (fr) *	1992-06-24	2006-12-19	Dorothea Isler	Aliments pour humains et animaux contenant un inhibiteur de la lipase
PL191222B1 (pl) *	1997-02-05	2006-03-31	Hoffmann La Roche	Zastosowanie tetrahydrolipstatyny do wytwarzania doustnego farmaceutycznego preparatu do leczenia cukrzycy typu II
SK141899A3 (en) *	1997-04-15	2000-09-12	Csir Corporate Building	Pharmaceutical compositions having appetite suppressant activity
GB2396815B (en) *	1999-10-27	2004-09-08	Phytopharm Plc	A composition comprising a pregnenone derivative and an NSAID
WO2001032670A1 (fr) *	1999-10-29	2001-05-10	John Jason Gentry Mullins	Dérivés d'oxétanone
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1985
- 1985-11-12 CA CA000495058A patent/CA1270837A/fr not_active Expired - Lifetime
- 1985-11-15 ZW ZW203/85A patent/ZW20385A1/xx unknown
- 1985-12-04 FI FI854797A patent/FI91403C/fi not_active IP Right Cessation
- 1985-12-09 CS CS859016A patent/CS262425B2/cs not_active IP Right Cessation
- 1985-12-16 NZ NZ214565A patent/NZ214565A/xx unknown
- 1985-12-16 IL IL77338A patent/IL77338A/xx not_active IP Right Cessation
- 1985-12-16 AU AU51259/85A patent/AU583569B2/en not_active Expired
- 1985-12-17 EP EP85116096A patent/EP0185359B1/fr not_active Expired - Lifetime
- 1985-12-17 AT AT85116096T patent/ATE70061T1/de not_active IP Right Cessation
- 1985-12-17 DE DE8585116096T patent/DE3584829D1/de not_active Expired - Lifetime
- 1985-12-18 PH PH33205A patent/PH26291A/en unknown
- 1985-12-18 HU HU854832A patent/HU200172B/hu unknown
- 1985-12-18 MC MC851814A patent/MC1728A1/fr unknown
- 1985-12-19 CN CN85108888A patent/CN1012643B/zh not_active Expired
- 1985-12-20 PT PT81748A patent/PT81748B/pt unknown
- 1985-12-20 NO NO855213A patent/NO171160C/no not_active IP Right Cessation
- 1985-12-20 IE IE327785A patent/IE58926B1/en not_active IP Right Cessation
- 1985-12-20 DK DK600385A patent/DK166724B1/da not_active IP Right Cessation
- 1985-12-30 DO DO1985004386A patent/DOP1985004386A/es unknown
1987
- 1987-12-17 US US07/134,322 patent/US4931463A/en not_active Expired - Lifetime
1990
- 1990-03-19 US US07/495,809 patent/US5175186A/en not_active Expired - Lifetime

Also Published As

Publication number	Publication date
US5175186A (en)	1992-12-29
ZW20385A1 (en)	1986-03-05
DK600385D0 (da)	1985-12-20
CN1012643B (zh)	1991-05-22
AU583569B2 (en)	1989-05-04
HUT39440A (en)	1986-09-29
IE58926B1 (en)	1993-12-01
EP0185359A3 (en)	1987-08-26
DK166724B1 (da)	1993-07-05
US4931463A (en)	1990-06-05
DK600385A (da)	1986-06-22
HU200172B (en)	1990-04-28
CN85108888A (zh)	1986-07-09
IL77338A (en)	1991-04-15
NO171160C (no)	1993-02-03
PH26291A (en)	1992-04-10
MC1728A1 (fr)	1986-12-15
FI854797A7 (fi)	1986-06-22
EP0185359A2 (fr)	1986-06-25
IE853277L (en)	1986-06-21
NZ214565A (en)	1989-06-28
NO855213L (no)	1986-06-23
NO171160B (no)	1992-10-26
AU5125985A (en)	1986-06-26
PT81748A (en)	1986-01-02
FI854797A0 (fi)	1985-12-04
CA1270837A (fr)	1990-06-26
ATE70061T1 (de)	1991-12-15
FI91403B (fi)	1994-03-15
DOP1985004386A (es)	1991-04-20
DE3584829D1 (de)	1992-01-16
FI91403C (fi)	1994-06-27
PT81748B (pt)	1988-07-29
EP0185359B1 (fr)	1991-12-04

Legal Events

Date	Code	Title	Description
2000-06-30	IF00	In force as of 2000-06-30 in czech republic
2001-02-14	MK4A	Patent expired	Effective date: 20001209

Publication	Publication Date	Title
US5175186A (en)	1992-12-29	Oxetanones
US5246960A (en)	1993-09-21	Oxetanones
US4983746A (en)	1991-01-08	Oxetanones and process for their production
Clive et al.	1990	Total synthesis of both (+)-compactin and (+)-mevinolin. A general strategy based on the use of a special titanium reagent for dicarbonyl coupling
HU208686B (en)	1993-12-28	Process for producing oxetanones
DE19645362A1 (de)	1998-04-30	Verfahren zur Herstellung von Epothilon A und B und Derivaten
US4503072A (en)	1985-03-05	Antihypercholesterolemic compounds
WO1995033716A1 (fr)	1995-12-14	Derive de la vitamine d3 et son procede de production
CS235329B2 (en)	1985-05-15	Method of 3-oxa-6a-carbaprostaglandine i 2 derivatives production
DK159313B (da)	1990-10-01	Analogifremgangsmaade til fremstilling af 5-cyanoprostacyklinderivater
KR950008310B1 (ko)	1995-07-27	옥세타논의 제조방법
JPH05178849A (ja)	1993-07-20	光学活性な含フッ素化合物
EP0164698B1 (fr)	1989-07-19	Procédé d'épimérisation sur le carbone 6 de 3,4,5,6-tétrahydro-2H-pyranne-2-one
Tadano et al.	1990	Stereoselectivity in the ortho ester Claisen rearrangements of the E and Z isomers of. gamma.-(1, 3-dioxan-4-yl) allyl alcohols
US4472426A (en)	1984-09-18	Antihypercholesterolemic compounds
US7122686B2 (en)	2006-10-17	Analogs of discodermolide and dictyostatin-1, intermediates therefor and methods of synthesis thereof
JPH0735365B2 (ja)	1995-04-19	カルシフエロ−ル誘導体
Kazmaier et al.	1998	A short synthesis of polyhydroxylated piperidines by aldol reaction of chelated amino acid ester enolates
CS271479B2 (en)	1990-10-12	Method of alpha-hydroxy-bicyclo/3,3,0/octane's derivatives production
US5849749A (en)	1998-12-15	6-(hydroxymethyl-ethyl)pyridines
US4526991A (en)	1985-07-02	2,6-Dioxa-bicyclo-[2,2,2]-octane-7-yl-acetaldehydes
Kametani et al.	1986	Novel construction of penem ring system from penicillin derivatives. Synthesis of a 2-carboxypenem derivative
Mukaiyama et al.	1986	A stereocontrolled synthesis of 2, 3, 5-trisubstituted tetrahydrofurans from aldolized γ-diketones via cyclization-reduction process
JPH041148A (ja)	1992-01-06	光学活性なアルケニル置換ヘプタン誘導体
Ikegami et al.	1992	Stereoselective Synthesis of (.+-.)-Ireland Alcohol Using Titanium-Mediated (2, 3) Wittig Rearrangement Product as a Starting Material.