FI74708B - Foerfarande foer framstaellning av 1rs,4sr,5rs-4-(4,8-dimetyl-5-hydroxi-7-nonen-1-yl)-4-metyl-3,8-dioxabicyklo /3.2.1/oktan-1-aettiksyra. - Google Patents
Foerfarande foer framstaellning av 1rs,4sr,5rs-4-(4,8-dimetyl-5-hydroxi-7-nonen-1-yl)-4-metyl-3,8-dioxabicyklo /3.2.1/oktan-1-aettiksyra. Download PDFInfo
- Publication number
- FI74708B FI74708B FI811351A FI811351A FI74708B FI 74708 B FI74708 B FI 74708B FI 811351 A FI811351 A FI 811351A FI 811351 A FI811351 A FI 811351A FI 74708 B FI74708 B FI 74708B
- Authority
- FI
- Finland
- Prior art keywords
- acid
- methyl
- formula
- dimethyl
- dioxabicyclo
- Prior art date
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- -1 4,8-DIMETHYL-5-HYDROXY-7-NONEN-1-YL Chemical class 0.000 title claims description 27
- 238000000034 method Methods 0.000 title claims description 11
- 239000000203 mixture Substances 0.000 claims description 39
- 150000001875 compounds Chemical class 0.000 claims description 16
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical group [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 15
- 239000002253 acid Substances 0.000 claims description 15
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims description 15
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 claims description 13
- 150000002148 esters Chemical class 0.000 claims description 12
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 claims description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 239000003795 chemical substances by application Substances 0.000 claims description 9
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 7
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 6
- HNZUNIKWNYHEJJ-FMIVXFBMSA-N geranyl acetone Chemical compound CC(C)=CCC\C(C)=C\CCC(C)=O HNZUNIKWNYHEJJ-FMIVXFBMSA-N 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 239000002585 base Substances 0.000 claims description 5
- 239000003638 chemical reducing agent Substances 0.000 claims description 5
- 150000004965 peroxy acids Chemical class 0.000 claims description 5
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
- YNJSNEKCXVFDKW-UHFFFAOYSA-N 3-(5-amino-1h-indol-3-yl)-2-azaniumylpropanoate Chemical compound C1=C(N)C=C2C(CC(N)C(O)=O)=CNC2=C1 YNJSNEKCXVFDKW-UHFFFAOYSA-N 0.000 claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 4
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 claims description 4
- HNZUNIKWNYHEJJ-UHFFFAOYSA-N geranyl acetone Natural products CC(C)=CCCC(C)=CCCC(C)=O HNZUNIKWNYHEJJ-UHFFFAOYSA-N 0.000 claims description 4
- 239000012280 lithium aluminium hydride Substances 0.000 claims description 4
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 239000012279 sodium borohydride Substances 0.000 claims description 4
- 229910000033 sodium borohydride Inorganic materials 0.000 claims description 4
- 239000012359 Methanesulfonyl chloride Substances 0.000 claims description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 3
- 229910001854 alkali hydroxide Inorganic materials 0.000 claims description 3
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 3
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 claims description 3
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 claims description 3
- KHIWWQKSHDUIBK-UHFFFAOYSA-N periodic acid Chemical compound OI(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-N 0.000 claims description 3
- IIHPVYJPDKJYOU-UHFFFAOYSA-N triphenylcarbethoxymethylenephosphorane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=CC(=O)OCC)C1=CC=CC=C1 IIHPVYJPDKJYOU-UHFFFAOYSA-N 0.000 claims description 3
- GLVYLTSKTCWWJR-UHFFFAOYSA-N 2-carbonoperoxoylbenzoic acid Chemical compound OOC(=O)C1=CC=CC=C1C(O)=O GLVYLTSKTCWWJR-UHFFFAOYSA-N 0.000 claims description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 2
- 239000012448 Lithium borohydride Substances 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- 230000003301 hydrolyzing effect Effects 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- 239000007800 oxidant agent Substances 0.000 claims 2
- 239000005642 Oleic acid Substances 0.000 claims 1
- 230000001476 alcoholic effect Effects 0.000 claims 1
- 230000000911 decarboxylating effect Effects 0.000 claims 1
- 125000005489 p-toluenesulfonic acid group Chemical group 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- LGBHIZIMKRKYDE-UHFFFAOYSA-N undeca-5,10-dien-2-one Chemical compound CC(=O)CCC=CCCCC=C LGBHIZIMKRKYDE-UHFFFAOYSA-N 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 109
- 239000000243 solution Substances 0.000 description 83
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 38
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 35
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 29
- 229920006395 saturated elastomer Polymers 0.000 description 25
- 238000006243 chemical reaction Methods 0.000 description 24
- 239000011734 sodium Substances 0.000 description 21
- 229910052757 nitrogen Inorganic materials 0.000 description 19
- 238000003756 stirring Methods 0.000 description 19
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
- 239000002904 solvent Substances 0.000 description 18
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 16
- 239000000284 extract Substances 0.000 description 16
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 239000005457 ice water Substances 0.000 description 10
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 239000012044 organic layer Substances 0.000 description 8
- 125000002619 bicyclic group Chemical group 0.000 description 7
- 235000019441 ethanol Nutrition 0.000 description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
- 150000002576 ketones Chemical class 0.000 description 7
- 239000010410 layer Substances 0.000 description 7
- VBTMMPMUTXKBBG-BYJZHYHWSA-N (5E)-undeca-1,5,9-triene Chemical compound C=CCC\C=C\CCC=CC VBTMMPMUTXKBBG-BYJZHYHWSA-N 0.000 description 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 6
- 239000012258 stirred mixture Substances 0.000 description 6
- LGBHIZIMKRKYDE-BQYQJAHWSA-N (5e)-undeca-5,10-dien-2-one Chemical compound CC(=O)CC\C=C\CCCC=C LGBHIZIMKRKYDE-BQYQJAHWSA-N 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
- 150000001299 aldehydes Chemical class 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 150000002596 lactones Chemical class 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- 239000003929 acidic solution Substances 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 150000002924 oxiranes Chemical class 0.000 description 4
- PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical compound COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 125000000143 2-carboxyethyl group Chemical group [H]OC(=O)C([H])([H])C([H])([H])* 0.000 description 3
- VOEJJDCBBKYZBU-UHFFFAOYSA-N 5-[5-(bromomethyl)-5-methoxyoxolan-2-yl]-5-methyloxolan-2-one Chemical compound O1C(OC)(CBr)CCC1C1(C)OC(=O)CC1 VOEJJDCBBKYZBU-UHFFFAOYSA-N 0.000 description 3
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 3
- XRDHAXIOHKTIGF-JECBFZOVSA-N Zoapatanol Chemical compound CC(C)=CCC(=O)[C@H](C)CCC[C@]1(C)OC\C(=C\CO)CC[C@H]1O XRDHAXIOHKTIGF-JECBFZOVSA-N 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 238000010828 elution Methods 0.000 description 3
- JZFQBWFDNWORAM-UHFFFAOYSA-N ethyl 2,6-dimethyl-3-oxohept-6-enoate Chemical compound CCOC(=O)C(C)C(=O)CCC(C)=C JZFQBWFDNWORAM-UHFFFAOYSA-N 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- DHKHKXVYLBGOIT-UHFFFAOYSA-N 1,1-Diethoxyethane Chemical compound CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 2
- GHVNFZFCNZKVNT-UHFFFAOYSA-N Decanoic acid Natural products CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 239000003810 Jones reagent Substances 0.000 description 2
- 229930194542 Keto Natural products 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- XRDHAXIOHKTIGF-UHFFFAOYSA-N Zoapatanol Natural products CC(C)=CCC(=O)C(C)CCCC1(C)OCC(=CCO)CCC1O XRDHAXIOHKTIGF-UHFFFAOYSA-N 0.000 description 2
- 150000004718 beta keto acids Chemical group 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- MOIPGXQKZSZOQX-UHFFFAOYSA-N carbonyl bromide Chemical compound BrC(Br)=O MOIPGXQKZSZOQX-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical compound [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 2
- 150000002085 enols Chemical class 0.000 description 2
- 239000012259 ether extract Substances 0.000 description 2
- FNENWZWNOPCZGK-UHFFFAOYSA-N ethyl 2-methyl-3-oxobutanoate Chemical compound CCOC(=O)C(C)C(C)=O FNENWZWNOPCZGK-UHFFFAOYSA-N 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 125000000468 ketone group Chemical group 0.000 description 2
- CDOSHBSSFJOMGT-UHFFFAOYSA-N linalool Chemical compound CC(C)=CCCC(C)(O)C=C CDOSHBSSFJOMGT-UHFFFAOYSA-N 0.000 description 2
- AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 2
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 2
- 239000002480 mineral oil Substances 0.000 description 2
- 235000010446 mineral oil Nutrition 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 125000005187 nonenyl group Chemical group C(=CCCCCCCC)* 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 235000009518 sodium iodide Nutrition 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- CRDAMVZIKSXKFV-FBXUGWQNSA-N (2-cis,6-cis)-farnesol Chemical compound CC(C)=CCC\C(C)=C/CC\C(C)=C/CO CRDAMVZIKSXKFV-FBXUGWQNSA-N 0.000 description 1
- 239000000260 (2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-ol Substances 0.000 description 1
- 239000001490 (3R)-3,7-dimethylocta-1,6-dien-3-ol Substances 0.000 description 1
- CDOSHBSSFJOMGT-JTQLQIEISA-N (R)-linalool Natural products CC(C)=CCC[C@@](C)(O)C=C CDOSHBSSFJOMGT-JTQLQIEISA-N 0.000 description 1
- DZKRDHLYQRTDBU-UPHRSURJSA-N (z)-but-2-enediperoxoic acid Chemical compound OOC(=O)\C=C/C(=O)OO DZKRDHLYQRTDBU-UPHRSURJSA-N 0.000 description 1
- SODQFLRLAOALCF-UHFFFAOYSA-N 1lambda3-bromacyclohexa-1,3,5-triene Chemical compound Br1=CC=CC=C1 SODQFLRLAOALCF-UHFFFAOYSA-N 0.000 description 1
- XYPISWUKQGWYGX-UHFFFAOYSA-N 2,2,2-trifluoroethaneperoxoic acid Chemical compound OOC(=O)C(F)(F)F XYPISWUKQGWYGX-UHFFFAOYSA-N 0.000 description 1
- JOGWMPMOQXUKPH-UHFFFAOYSA-N 2-(3,8-dioxabicyclo[3.2.1]octan-5-yl)ethanol Chemical compound C1OCC2CCC1(CCO)O2 JOGWMPMOQXUKPH-UHFFFAOYSA-N 0.000 description 1
- YWJYHOMUEWSGQJ-UHFFFAOYSA-N 3,8-dioxabicyclo[3.2.1]octane Chemical compound C1OCC2CCC1O2 YWJYHOMUEWSGQJ-UHFFFAOYSA-N 0.000 description 1
- OHXAOPZTJOUYKM-UHFFFAOYSA-N 3-Chloro-2-methylpropene Chemical compound CC(=C)CCl OHXAOPZTJOUYKM-UHFFFAOYSA-N 0.000 description 1
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 1
- XRDHAXIOHKTIGF-UKHUEATNSA-N 9-[(2r,3s,6e)-3-hydroxy-6-(2-hydroxyethylidene)-2-methyloxepan-2-yl]-2,6-dimethylnon-2-en-5-one Chemical compound CC(C)=CCC(=O)C(C)CCC[C@@]1(C)OC\C(=C\CO)CC[C@@H]1O XRDHAXIOHKTIGF-UKHUEATNSA-N 0.000 description 1
- 125000006519 CCH3 Chemical group 0.000 description 1
- 101100219382 Caenorhabditis elegans cah-2 gene Proteins 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- WTEVQBCEXWBHNA-UHFFFAOYSA-N Citral Natural products CC(C)=CCCC(C)=CC=O WTEVQBCEXWBHNA-UHFFFAOYSA-N 0.000 description 1
- 229910004373 HOAc Inorganic materials 0.000 description 1
- 239000007832 Na2SO4 Substances 0.000 description 1
- 229910020889 NaBH3 Inorganic materials 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 238000007239 Wittig reaction Methods 0.000 description 1
- YTAHJIFKAKIKAV-XNMGPUDCSA-N [(1R)-3-morpholin-4-yl-1-phenylpropyl] N-[(3S)-2-oxo-5-phenyl-1,3-dihydro-1,4-benzodiazepin-3-yl]carbamate Chemical compound O=C1[C@H](N=C(C2=C(N1)C=CC=C2)C1=CC=CC=C1)NC(O[C@H](CCN1CCOCC1)C1=CC=CC=C1)=O YTAHJIFKAKIKAV-XNMGPUDCSA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 150000001266 acyl halides Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- YHASWHZGWUONAO-UHFFFAOYSA-N butanoyl butanoate Chemical compound CCCC(=O)OC(=O)CCC YHASWHZGWUONAO-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- RBHJBMIOOPYDBQ-UHFFFAOYSA-N carbon dioxide;propan-2-one Chemical compound O=C=O.CC(C)=O RBHJBMIOOPYDBQ-UHFFFAOYSA-N 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 229940043350 citral Drugs 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 229930007927 cymene Natural products 0.000 description 1
- 238000006114 decarboxylation reaction Methods 0.000 description 1
- 230000000779 depleting effect Effects 0.000 description 1
- 229940043279 diisopropylamine Drugs 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- CEXUZYMPCXKVSG-UHFFFAOYSA-N ethyl 2-[2-(5-acetyloxy-4,8-dimethylnon-8-enyl)-2-methyl-3,8-dioxabicyclo[3.2.1]octan-5-yl]acetate Chemical compound O1C2CCC1(CC(=O)OCC)COC2(CCCC(C)C(CCC(C)=C)OC(C)=O)C CEXUZYMPCXKVSG-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 229940043259 farnesol Drugs 0.000 description 1
- 229930002886 farnesol Natural products 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- WTEVQBCEXWBHNA-JXMROGBWSA-N geranial Chemical compound CC(C)=CCC\C(C)=C\C=O WTEVQBCEXWBHNA-JXMROGBWSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 229930007744 linalool Natural products 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- PGTMYXAQLPHCAL-UHFFFAOYSA-N oxepan-3-ol Chemical compound OC1CCCCOC1 PGTMYXAQLPHCAL-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- HFPZCAJZSCWRBC-UHFFFAOYSA-N p-cymene Chemical compound CC(C)C1=CC=C(C)C=C1 HFPZCAJZSCWRBC-UHFFFAOYSA-N 0.000 description 1
- 239000003880 polar aprotic solvent Substances 0.000 description 1
- CHKVPAROMQMJNQ-UHFFFAOYSA-M potassium bisulfate Chemical compound [K+].OS([O-])(=O)=O CHKVPAROMQMJNQ-UHFFFAOYSA-M 0.000 description 1
- 229910000343 potassium bisulfate Inorganic materials 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000008237 rinsing water Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- CRDAMVZIKSXKFV-UHFFFAOYSA-N trans-Farnesol Natural products CC(C)=CCCC(C)=CCCC(C)=CCO CRDAMVZIKSXKFV-UHFFFAOYSA-N 0.000 description 1
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 description 1
- RCFOEQFXUGQOMT-UHFFFAOYSA-N undeca-3,5-dien-2-one Chemical compound CCCCCC=CC=CC(C)=O RCFOEQFXUGQOMT-UHFFFAOYSA-N 0.000 description 1
- JQSHBVHOMNKWFT-DTORHVGOSA-N varenicline Chemical compound C12=CC3=NC=CN=C3C=C2[C@H]2C[C@@H]1CNC2 JQSHBVHOMNKWFT-DTORHVGOSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/08—Bridged systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/32—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by aldehydo- or ketonic radicals
-
- 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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Epoxy Compounds (AREA)
Claims (5)
1. Nytt förfarande för framställning av 1RS,4SR,5RS- 4-(4,8-dimetyl-5-hydroxi-7-nonen-l-yl)-4-metyl-3,8-dioxabi-cyklo^3.2.l^oktan-l-äftiksyra med formeln 5 0H j—sv^.ch2cooh CH CH- 10 3 3 kännetecknat därav, att genanylaceton med formeln omsättes med trimetylsilylklorid för bildande av 6,10-di-20 metyl-2-trimetylsilyloxi-5(E)-1,5,9-undekatrien med formeln / WO-TMS Y den erh&llna föreningen omsätts med ett bromeringsmedel sä-som N-bromsuccinimid för bildande av l-brom-6,10-dimetyl-30 5 (E)-5,10-undekadien-2-on med formeln vXC 35 ' 33 74708 den bildade föreningen omsätts med en peroxid, peroxisyra säsom m-klorperoxibensoesyra; perättiksyra, permaleinsyra, perbensoesyra, perftalsyra eller pertrifluorättiksyra, för bildande av l-brom-6,10-dimetyl-9,10-oxido-5(E)-undeken- 2-on med forme In den bildade föreningen omsätts med perjodsyra för bildande av l-brom-6-metyl-2-oxo-5(E)-nonen-9-al med formeln <>; den bildade föreningen omsätts med ett oxidationsmedel sä-
2-C som en CrO^-I^SC^-blandning för bildande av l-brom-6-metyl- 2-oxo-5(E)-nonen-9-syra med formeln 25 den bildade föreningen omsätts med en peroxisyra säsom m-klorperoxibensoesyra, perbensoesyra eller perftalsyra för 30 bildande av ett brom-hemiketal-"^-lakton med formeln 35 34 74708 den bildade föreningen omsätts med ett trialkylortoformiat för bildande av en blandning av cis/trans-2-(2-brommetyl- 2-metoxitetrahydrofuran-5-yl)-2-metyl-5-oxotetrahydrofuran i vilken beständsdelarna har formlerna 5 /v*"3 ry-Br 10 det bildade cis-2-(2-brommetyl-2-metoxitetrahydrofuran-5-yl)-2-metyl-5-oxotetrahydrofuranet cykliseras med en alka-lihydroxid till IRS,4RS,5RS-4-(2-karboxietyl)-l-metoxi-4-15 metyl-3,8-dioxabicyklo£§.2.l^oktan med formeln 0 /—\0CH. HO X 7s· 0 J
20 CH3 den bildade föreningen omsätts med ett reduceringsmedel s&-som borhydrid för bildande av IRS,4RS,5SR-4-(2-hydroxietyl)-25 l-metoxi-4-metyl-3,8-dioxabicyklo/3.2.l^oktan med formeln HO —.OCH^
30 To ch3 den bildade föreningen omsätts med metansulfonylklorid för bildande av IRS,4RS,5SR-4-(2-metansulfonyloxipropyl)-1-35 metoxi-4-metyl-3,8-dioxabicyklo/_3.2. l^oktan med formeln 3 7470 8 35 MS? /-V ^OCH CH3 5 den bildade föreningen omsätts med alkyl-2,6-dimetyl-3-oxo- 6-heptenoat med formeln O 10 'γ'-'^cs^'ch3 'COOR^ för bildande av IRS,4RS,5SR-l-metoxi-4-metyl-4-(4-alkoxi-karbonyl-4,8-dimetyl-5-oxo-8-nonenyl)-3,8-dioxabicyklo-15 /.3.2. l^oktan med formeln O COOR, / \---0CH3 CH_ CH- 20 3 3 den bildade föreningen hydrolyseras och dekarboxyleras kar-bonsyraestern med en bas säsom aikaiihydroxid i en vatten-alkoholblandning för bildande av IRS,4RS,5SR-l-metoxi-4-metyl-4-(4,8-dimetyl-5-oxo-8-nonenyl)-3,8-dioxabicyklo-£3.2.l7oktan med formeln O / V^OCH 3
30 CH3 CH3 den bildade föreningen reduceras med ett andra reduktions-medel säsom natriumborhydrid, litiumborhydrid eller litium-aluminiumhydrid för bildande av IRS,4RS,5SR-l-metoxi-4-metyl-4-(5-hydroxi-4,8-dimetyl-8-nonenyl)-3,8-dioxabicyklo-/3.2.l7oktan med formeln ?H / \J3CH 40 * ch3 ch3 36 74708 den bildade föreningen förestras med ett förestringsmedel setsom en syrahalogenid eller karboxylsyraanhydrid för bil-dande av lRS,4RS,5SR-l-metoxi-4-metyl-4-(5-acyloxi-4,8-di-metyl-8-nonenyl)-3,8-dioxabicyklo£3.2.l^oktan med formeln 5 ch3 ch 10 den bildade föreningen omsätts med en stark syra sdsom klor-väte, svavelsyra eller fosforsyra för framställning av IRS,4RS,5SR-l-hydroxi-4-metyl-4-(5-acyloxi-4,8-dimetyl-8-nonenyl)-3,8-dioxabicyklo^3.2.l^oktan med formeln 15 0R2 /—v OH , CH3 2u J den bildade föreningen omsätts med (karbetoximetylen)tri- fenylfosforan för bildande av alkyl-(IRS,4SR,5RS)-4-(5-acyloxi-4,0-dimetyl-8-nonenyl)-4-metyl-3,8-dioxabicyklo-(3.2.l^oktanacetat med formeln 25 °R2 / V^CH.COOR \ S yo O1'4 '1 ^ 1 CH CH, 30 3 3 den bildade föreningen isomeriseras med ett isomeriserings- medel säsom p-toluensulfonsyra till alkyl-(IRS,4SR,5RS)-4-(5-acyloxi-4,8-dimetyl-7-nonenyl)-4-metyl-3,8-dioxabicyklo-35 .2.Ooktan-l-asetat med formeln
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FI873254A FI873254A0 (fi) | 1980-05-02 | 1987-07-24 | 1rs,4sr,5rs-4-(4,8-dimetyl-5-hydroxi -8-nonen-1-yl)-4-metyl-3,8-dioxabicyklo/3.2.1/oktan-1-aettikssyra och foerfarande foer dess framstaellning. |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/146,538 US4284565A (en) | 1980-05-02 | 1980-05-02 | Total synthesis of 1RS,4SR,5RS-4-(4,8-dimethyl)-5-hydroxy-7-nonen-1-yl)-4-methyl-3,8-dioxabicyclo[3.2.1]octane-1-acetic acid and related compounds |
| US14653880 | 1980-05-02 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI811351L FI811351L (fi) | 1981-11-03 |
| FI74708B true FI74708B (fi) | 1987-11-30 |
| FI74708C FI74708C (sv) | 1988-03-10 |
Family
ID=22517836
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI811351A FI74708C (sv) | 1980-05-02 | 1981-04-29 | Förfarande för framställning av 1RS,4SR,5RS-4-(4,8-dimetyl-5-hydroxi-7 -nonen-1-yl)-4-metyl-3,8-dioxabi/3.2.1/oktan-1-ättiksyra. |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US4284565A (sv) |
| EP (2) | EP0116375B1 (sv) |
| JP (1) | JPS56169692A (sv) |
| KR (1) | KR850000046B1 (sv) |
| AU (1) | AU536915B2 (sv) |
| CA (1) | CA1170266A (sv) |
| DE (1) | DE3169505D1 (sv) |
| DK (1) | DK151966B (sv) |
| ES (1) | ES501775A0 (sv) |
| FI (1) | FI74708C (sv) |
| GR (1) | GR67294B (sv) |
| IE (1) | IE52148B1 (sv) |
| IL (1) | IL62768A (sv) |
| NO (1) | NO152415C (sv) |
| NZ (1) | NZ196835A (sv) |
| PH (1) | PH16215A (sv) |
| YU (1) | YU112281A (sv) |
| ZA (1) | ZA812923B (sv) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4603213A (en) * | 1984-09-27 | 1986-07-29 | Ortho Pharmaceutical Corporation | Total synthesis of 1RS,4SR,5RS-4-(4,8-dimethyl-5-hydroxy-7-nonen-1-yl)-4-methyl-3,8-dioxabicyclo[3.2.1]octane-1-acetic acid |
| GB2348879B (en) | 1999-04-16 | 2004-03-31 | Hydron Ltd | Process |
| US7905183B2 (en) * | 2008-01-29 | 2011-03-15 | Gibson Daniel J | Structural cardboard runner, pallet, shipping article |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2322821A (en) * | 1940-06-22 | 1943-06-29 | Atlas Powder Co | Partial esters of ethers of polyhydroxylic compounds |
| US2771471A (en) * | 1950-12-01 | 1956-11-20 | Petrolite Corp | Polycarboxy acid esters of oxypropylated hexides |
| US4102895A (en) * | 1976-11-18 | 1978-07-25 | Ortho Pharmaceutical Corporation | Oxepanes |
| US4237055A (en) * | 1979-06-18 | 1980-12-02 | Ortho Pharmaceutical Corporation | Synthesis of 1RS,4SR,5RS-4-(4,8-dimethyl-5-hydroxy-7-nonen-1-yl)-4-methyl-3,8-dioxabicyclo[3.2.1]octane-1-acetic acid |
-
1980
- 1980-05-02 US US06/146,538 patent/US4284565A/en not_active Expired - Lifetime
-
1981
- 1981-04-02 CA CA000374497A patent/CA1170266A/en not_active Expired
- 1981-04-13 PH PH25494A patent/PH16215A/en unknown
- 1981-04-14 KR KR1019810001261A patent/KR850000046B1/ko active IP Right Grant
- 1981-04-15 NZ NZ196835A patent/NZ196835A/xx unknown
- 1981-04-21 JP JP5932581A patent/JPS56169692A/ja active Pending
- 1981-04-28 AU AU69903/81A patent/AU536915B2/en not_active Ceased
- 1981-04-29 GR GR64810A patent/GR67294B/el unknown
- 1981-04-29 FI FI811351A patent/FI74708C/sv not_active IP Right Cessation
- 1981-04-29 ES ES501775A patent/ES501775A0/es active Granted
- 1981-04-30 IE IE965/81A patent/IE52148B1/en unknown
- 1981-04-30 NO NO811475A patent/NO152415C/no unknown
- 1981-04-30 YU YU01122/81A patent/YU112281A/xx unknown
- 1981-04-30 IL IL62768A patent/IL62768A/xx unknown
- 1981-05-01 EP EP84200026A patent/EP0116375B1/en not_active Expired
- 1981-05-01 DE DE8181301934T patent/DE3169505D1/de not_active Expired
- 1981-05-01 DK DK195381AA patent/DK151966B/da not_active Application Discontinuation
- 1981-05-01 EP EP81301934A patent/EP0039595B1/en not_active Expired
- 1981-05-01 ZA ZA00812923A patent/ZA812923B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU536915B2 (en) | 1984-05-31 |
| NO152415B (no) | 1985-06-17 |
| DK195381A (da) | 1981-11-03 |
| DK151966B (da) | 1988-01-18 |
| NO152415C (no) | 1985-09-25 |
| IE52148B1 (en) | 1987-07-08 |
| ES8207542A1 (es) | 1982-09-16 |
| ES501775A0 (es) | 1982-09-16 |
| KR850000046B1 (ko) | 1985-02-14 |
| EP0039595A1 (en) | 1981-11-11 |
| NZ196835A (en) | 1983-11-18 |
| CA1170266A (en) | 1984-07-03 |
| EP0116375B1 (en) | 1986-11-12 |
| FI74708C (sv) | 1988-03-10 |
| DE3169505D1 (en) | 1985-05-02 |
| ZA812923B (en) | 1982-12-29 |
| IE810965L (en) | 1981-11-02 |
| EP0116375A1 (en) | 1984-08-22 |
| FI811351L (fi) | 1981-11-03 |
| GR67294B (sv) | 1981-06-29 |
| US4284565A (en) | 1981-08-18 |
| AU6990381A (en) | 1981-11-05 |
| IL62768A0 (en) | 1981-06-29 |
| YU112281A (en) | 1983-09-30 |
| NO811475L (no) | 1981-11-03 |
| PH16215A (en) | 1983-08-05 |
| IL62768A (en) | 1984-03-30 |
| JPS56169692A (en) | 1981-12-26 |
| EP0039595B1 (en) | 1985-03-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed |
Owner name: ORTHO PHARMACEUTICAL CORPORATION |