CH622021A5 - - Google Patents
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- Publication number
- CH622021A5 CH622021A5 CH1214176A CH1214176A CH622021A5 CH 622021 A5 CH622021 A5 CH 622021A5 CH 1214176 A CH1214176 A CH 1214176A CH 1214176 A CH1214176 A CH 1214176A CH 622021 A5 CH622021 A5 CH 622021A5
- Authority
- CH
- Switzerland
- Prior art keywords
- formula
- compound
- preparation
- decane
- formula vii
- Prior art date
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- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 claims description 42
- 238000002360 preparation method Methods 0.000 claims description 36
- 150000001875 compounds Chemical class 0.000 claims description 35
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 17
- 241000251730 Chondrichthyes Species 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 229910052987 metal hydride Inorganic materials 0.000 claims description 9
- 150000004681 metal hydrides Chemical class 0.000 claims description 9
- PHHROXLDZHUIGO-PNBTUHDLSA-N Didrovaltratum Chemical compound C([C@@]12[C@@H](OC(C)=O)C[C@H]3[C@@H]1[C@H](OC(=O)CC(C)C)OC=C3COC(=O)CC(C)C)O2 PHHROXLDZHUIGO-PNBTUHDLSA-N 0.000 claims description 8
- 125000004423 acyloxy group Chemical group 0.000 claims description 8
- PHHROXLDZHUIGO-UHFFFAOYSA-N dihydrovaltrate Natural products CC(C)CC(=O)OCC1=COC(OC(=O)CC(C)C)C2C1CC(OC(C)=O)C21CO1 PHHROXLDZHUIGO-UHFFFAOYSA-N 0.000 claims description 8
- -1 alkyl isocyanates Chemical class 0.000 claims description 7
- ZPSOISAMGWYNQX-UHFFFAOYSA-N non-6-enoic acid Chemical compound CCC=CCCCCC(O)=O ZPSOISAMGWYNQX-UHFFFAOYSA-N 0.000 claims description 7
- 230000003647 oxidation Effects 0.000 claims description 7
- 238000007254 oxidation reaction Methods 0.000 claims description 7
- 239000007868 Raney catalyst Substances 0.000 claims description 6
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims description 6
- 229910000564 Raney nickel Inorganic materials 0.000 claims description 6
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 claims description 6
- 229940112021 centrally acting muscle relaxants carbamic acid ester Drugs 0.000 claims description 6
- 239000000284 extract Substances 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 239000012948 isocyanate Substances 0.000 claims description 6
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 150000002148 esters Chemical class 0.000 claims description 5
- 150000002596 lactones Chemical class 0.000 claims description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 4
- JDPQWHLMBJZURR-UHFFFAOYSA-N decan-5-one Chemical compound CCCCCC(=O)CCCC JDPQWHLMBJZURR-UHFFFAOYSA-N 0.000 claims description 4
- 125000000468 ketone group Chemical group 0.000 claims description 4
- ZAJNGDIORYACQU-UHFFFAOYSA-N methyl n-octyl ketone Natural products CCCCCCCCC(C)=O ZAJNGDIORYACQU-UHFFFAOYSA-N 0.000 claims description 4
- VLXMVSDUQKULHU-UHFFFAOYSA-N 2,9-dioxatricyclo[4.3.1.03,7]decane Chemical compound C1C2CCC3C2COC1O3 VLXMVSDUQKULHU-UHFFFAOYSA-N 0.000 claims description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 3
- 150000008282 halocarbons Chemical class 0.000 claims description 3
- 239000012433 hydrogen halide Substances 0.000 claims description 3
- 229910000039 hydrogen halide Inorganic materials 0.000 claims description 3
- 230000001590 oxidative effect Effects 0.000 claims description 3
- 150000003138 primary alcohols Chemical class 0.000 claims description 3
- 238000006798 ring closing metathesis reaction Methods 0.000 claims description 3
- 125000002252 acyl group Chemical group 0.000 claims 1
- 125000001475 halogen functional group Chemical group 0.000 claims 1
- 229910052751 metal Inorganic materials 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 96
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 75
- 239000000203 mixture Substances 0.000 description 41
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 39
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 38
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 31
- 239000012071 phase Substances 0.000 description 25
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 22
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 20
- 239000000243 solution Substances 0.000 description 15
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 14
- 238000001704 evaporation Methods 0.000 description 14
- 230000008020 evaporation Effects 0.000 description 14
- 239000000741 silica gel Substances 0.000 description 14
- 229910002027 silica gel Inorganic materials 0.000 description 14
- 238000003756 stirring Methods 0.000 description 14
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 13
- 238000009419 refurbishment Methods 0.000 description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 229910052938 sodium sulfate Inorganic materials 0.000 description 9
- 235000011152 sodium sulphate Nutrition 0.000 description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 239000003054 catalyst Substances 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 229960000583 acetic acid Drugs 0.000 description 5
- MKJDUHZPLQYUCB-UHFFFAOYSA-N decan-4-one Chemical compound CCCCCCC(=O)CCC MKJDUHZPLQYUCB-UHFFFAOYSA-N 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- JCIIKRHCWVHVFF-UHFFFAOYSA-N 1,2,4-thiadiazol-5-amine;hydrochloride Chemical compound Cl.NC1=NC=NS1 JCIIKRHCWVHVFF-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 239000003480 eluent Substances 0.000 description 4
- BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 4
- 229940096826 phenylmercuric acetate Drugs 0.000 description 4
- XEBWQGVWTUSTLN-UHFFFAOYSA-M phenylmercury acetate Chemical compound CC(=O)O[Hg]C1=CC=CC=C1 XEBWQGVWTUSTLN-UHFFFAOYSA-M 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- GSLTVFIVJMCNBH-UHFFFAOYSA-N 2-isocyanatopropane Chemical compound CC(C)N=C=O GSLTVFIVJMCNBH-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- 230000000202 analgesic effect Effects 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- XLMALTXPSGQGBX-GCJKJVERSA-N dextropropoxyphene Chemical compound C([C@](OC(=O)CC)([C@H](C)CN(C)C)C=1C=CC=CC=1)C1=CC=CC=C1 XLMALTXPSGQGBX-GCJKJVERSA-N 0.000 description 2
- 229960004193 dextropropoxyphene Drugs 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
- 229940071870 hydroiodic acid Drugs 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 2
- 229960005181 morphine Drugs 0.000 description 2
- HNHVTXYLRVGMHD-UHFFFAOYSA-N n-butyl isocyanate Chemical compound CCCCN=C=O HNHVTXYLRVGMHD-UHFFFAOYSA-N 0.000 description 2
- 229910017604 nitric acid Inorganic materials 0.000 description 2
- BSCCSDNZEIHXOK-UHFFFAOYSA-N phenyl carbamate Chemical compound NC(=O)OC1=CC=CC=C1 BSCCSDNZEIHXOK-UHFFFAOYSA-N 0.000 description 2
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 2
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 2
- OVPLZYJGTGDFNB-UHFFFAOYSA-N propan-2-yl carbamate Chemical compound CC(C)OC(N)=O OVPLZYJGTGDFNB-UHFFFAOYSA-N 0.000 description 2
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000013558 reference substance Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- OOBHFESNSZDWIU-GXSJLCMTSA-N (2s,3s)-3-methyl-2-phenylmorpholine Chemical compound C[C@@H]1NCCO[C@H]1C1=CC=CC=C1 OOBHFESNSZDWIU-GXSJLCMTSA-N 0.000 description 1
- YCTDZYMMFQCTEO-FNORWQNLSA-N (E)-3-octene Chemical compound CCCC\C=C\CC YCTDZYMMFQCTEO-FNORWQNLSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- USSIQXCVUWKGNF-UHFFFAOYSA-N 6-(dimethylamino)-4,4-diphenylheptan-3-one Chemical group C=1C=CC=CC=1C(CC(C)N(C)C)(C(=O)CC)C1=CC=CC=C1 USSIQXCVUWKGNF-UHFFFAOYSA-N 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- KQEOKUJOWVGWDX-UHFFFAOYSA-N Isodihydrovaltrate Natural products CC(C)CC(=O)OC1CC(C(=COC2OC(=O)CC(C)C)COC(C)=O)C2C11CO1 KQEOKUJOWVGWDX-UHFFFAOYSA-N 0.000 description 1
- 239000003810 Jones reagent Substances 0.000 description 1
- 229910010082 LiAlH Inorganic materials 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical class [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- 101100054666 Streptomyces halstedii sch3 gene Proteins 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 230000036592 analgesia Effects 0.000 description 1
- 229940035676 analgesics Drugs 0.000 description 1
- 230000001539 anorectic effect Effects 0.000 description 1
- 239000000730 antalgic agent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- SKKTUOZKZKCGTB-UHFFFAOYSA-N butyl carbamate Chemical compound CCCCOC(N)=O SKKTUOZKZKCGTB-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003874 central nervous system depressant Substances 0.000 description 1
- 238000013016 damping Methods 0.000 description 1
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 1
- 229950005934 didrovaltrate Drugs 0.000 description 1
- PVKOJQHHDYMUEI-UHFFFAOYSA-N didrovaltrate Natural products CC(C)CC(=O)COC1=COC(OC(=O)CC(C)C)C2C1CC(OC(=O)C)C23CO3 PVKOJQHHDYMUEI-UHFFFAOYSA-N 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 150000002440 hydroxy compounds Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000000147 hypnotic effect Effects 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229960001797 methadone Drugs 0.000 description 1
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
- ZZHGIUCYKGFIPV-UHFFFAOYSA-M n-butylcarbamate Chemical compound CCCCNC([O-])=O ZZHGIUCYKGFIPV-UHFFFAOYSA-M 0.000 description 1
- 230000003533 narcotic effect Effects 0.000 description 1
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- OOBHFESNSZDWIU-UHFFFAOYSA-N phenmetrazine Chemical compound CC1NCCOC1C1=CC=CC=C1 OOBHFESNSZDWIU-UHFFFAOYSA-N 0.000 description 1
- 229960003209 phenmetrazine Drugs 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- XSVKAYYNFNXTDA-BGCDDMGFSA-N solanapyrone f Chemical compound C1([C@H]2[C@@H]3CC[C@H](O)C[C@@H]3C=C[C@@H]2C)=CC(N)=C(C=O)C(=O)O1 XSVKAYYNFNXTDA-BGCDDMGFSA-N 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 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
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 230000000304 vasodilatating effect Effects 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- 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
- A61P3/04—Anorexiants; Antiobesity agents
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Neurology (AREA)
- Child & Adolescent Psychology (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Pain & Pain Management (AREA)
- Biomedical Technology (AREA)
- Diabetes (AREA)
- Neurosurgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pyrane Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2547205A DE2547205C2 (de) | 1975-10-22 | 1975-10-22 | 2,9-Dioxatricyclo[4,3,1,0↑3↑↑,↑↑7↑]decane und Verfahren zu deren Herstellung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH622021A5 true CH622021A5 (cs) | 1981-03-13 |
Family
ID=5959735
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1214176A CH622021A5 (cs) | 1975-10-22 | 1976-09-24 |
Country Status (28)
| Country | Link |
|---|---|
| US (2) | US4089971A (cs) |
| JP (3) | JPS5251399A (cs) |
| AT (1) | AT346853B (cs) |
| AU (1) | AU505725B2 (cs) |
| BE (1) | BE847302A (cs) |
| CA (1) | CA1095060A (cs) |
| CH (1) | CH622021A5 (cs) |
| CS (1) | CS203993B2 (cs) |
| DD (1) | DD128704A5 (cs) |
| DE (1) | DE2547205C2 (cs) |
| DK (1) | DK475376A (cs) |
| ES (2) | ES452174A1 (cs) |
| FI (1) | FI762572A (cs) |
| FR (2) | FR2361876A1 (cs) |
| GB (2) | GB1560653A (cs) |
| GR (1) | GR72587B (cs) |
| HU (1) | HU176688B (cs) |
| IE (1) | IE43872B1 (cs) |
| IL (1) | IL50554A (cs) |
| MX (1) | MX4958E (cs) |
| NL (1) | NL7609625A (cs) |
| NO (1) | NO145239C (cs) |
| PH (1) | PH14457A (cs) |
| PL (1) | PL110266B1 (cs) |
| PT (1) | PT65685B (cs) |
| SE (1) | SE421696B (cs) |
| YU (1) | YU258476A (cs) |
| ZA (1) | ZA765642B (cs) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2547205C2 (de) * | 1975-10-22 | 1983-12-08 | Kali-Chemie Pharma Gmbh, 3000 Hannover | 2,9-Dioxatricyclo[4,3,1,0↑3↑↑,↑↑7↑]decane und Verfahren zu deren Herstellung |
| DE2607106C2 (de) | 1976-02-21 | 1986-01-16 | Kali-Chemie Pharma Gmbh, 3000 Hannover | 2,9-Dioxatricyclo[4,3,1,0↑3↑↑,↑↑7↑]decane und Verfahren zu deren Herstellung |
| US4158061A (en) * | 1976-02-21 | 1979-06-12 | Kali-Chemie Pharma Gmbh | 2,9-Dioxatricyclo[4,3,1,03,7 ] decane derivatives, processes for their preparation and pharmaceutical compositions thereof |
| DE2730988A1 (de) | 1977-07-08 | 1979-01-25 | Kali Chemie Pharma Gmbh | 3-azidomethyl-2,9-dioxatricyclo eckige klammer auf 4,3,1,0 hoch 3,7 eckige klammer zu decane und verfahren zu deren herstellung |
| US4677190A (en) * | 1986-05-09 | 1987-06-30 | University Patents, Inc. | Synthesis and ring-opening polymerization of bicyclic lactones containing a tetrahydropyran ring |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3812154A (en) * | 1969-12-08 | 1974-05-21 | Kali Chemie Ag | Dioxatricyclodecanes |
| US3917651A (en) * | 1969-12-08 | 1975-11-04 | Kali Chemie Ag | Dioxatricyclodecanones |
| BE759840A (fr) | 1969-12-08 | 1971-05-17 | Kali Chemie Ag | 2,9-dioxatricyclo-(4,3,1,0,3,7)-decanes et procede pour les preparer |
| US4016176A (en) * | 1973-02-08 | 1977-04-05 | Kali-Chemie Pharma Gmbh | Esters of 4-hydroxy-2,9-dioxatricyclo[4.3.1.03,7 ] decanes and processes for their production |
| US4189437A (en) * | 1975-10-22 | 1980-02-19 | Kali-Chemie Pharma Gmbh | Pharmaceutically active 2,9-dioxatricyclo[4,3,1,03,7 ]decanes |
| DE2547205C2 (de) * | 1975-10-22 | 1983-12-08 | Kali-Chemie Pharma Gmbh, 3000 Hannover | 2,9-Dioxatricyclo[4,3,1,0↑3↑↑,↑↑7↑]decane und Verfahren zu deren Herstellung |
| US4158061A (en) * | 1976-02-21 | 1979-06-12 | Kali-Chemie Pharma Gmbh | 2,9-Dioxatricyclo[4,3,1,03,7 ] decane derivatives, processes for their preparation and pharmaceutical compositions thereof |
| DE2704621A1 (de) * | 1977-02-04 | 1978-08-10 | Kali Chemie Pharma Gmbh | 2,9-dioxatricyclo eckige klammer auf 4,3,1,0 hoch 3,7 eckige klammer zu decane und verfahren zu deren herstellung |
| DE2719916C2 (de) * | 1977-05-04 | 1987-03-19 | Kali-Chemie Pharma Gmbh, 3000 Hannover | Verfahren zur Herstellung von 2,9-Dioxatricyclo[4,3,1,0↑3↑↑,↑↑7↑]decanen |
| US4117148A (en) * | 1977-02-18 | 1978-09-26 | Kali-Chemie Pharma Gmbh. | 2,9-Dioxatricyclo [4,3,1,0,3,7] decane derivatives, processes for their preparation and pharmaceutical compositions thereof |
-
1975
- 1975-10-22 DE DE2547205A patent/DE2547205C2/de not_active Expired
-
1976
- 1976-08-30 NL NL7609625A patent/NL7609625A/xx unknown
- 1976-09-07 GB GB2222/79A patent/GB1560653A/en not_active Expired
- 1976-09-07 GB GB37065/76A patent/GB1560652A/en not_active Expired
- 1976-09-07 FI FI762572A patent/FI762572A/fi not_active Application Discontinuation
- 1976-09-08 MX MX764893U patent/MX4958E/es unknown
- 1976-09-21 ZA ZA765642A patent/ZA765642B/xx unknown
- 1976-09-21 IE IE2082/76A patent/IE43872B1/en unknown
- 1976-09-24 CH CH1214176A patent/CH622021A5/de not_active IP Right Cessation
- 1976-09-24 IL IL50554A patent/IL50554A/xx unknown
- 1976-09-29 AU AU18206/76A patent/AU505725B2/en not_active Expired
- 1976-10-01 AT AT731376A patent/AT346853B/de not_active IP Right Cessation
- 1976-10-04 CS CS766409A patent/CS203993B2/cs unknown
- 1976-10-06 HU HU76KA1473A patent/HU176688B/hu unknown
- 1976-10-07 PT PT65685A patent/PT65685B/pt unknown
- 1976-10-07 ES ES452174A patent/ES452174A1/es not_active Expired
- 1976-10-11 SE SE7611269A patent/SE421696B/xx unknown
- 1976-10-14 BE BE6045715A patent/BE847302A/xx not_active IP Right Cessation
- 1976-10-15 US US05/732,791 patent/US4089971A/en not_active Expired - Lifetime
- 1976-10-18 PH PH19015A patent/PH14457A/en unknown
- 1976-10-18 FR FR7631241A patent/FR2361876A1/fr active Granted
- 1976-10-20 DD DD7600195372A patent/DD128704A5/xx unknown
- 1976-10-21 PL PL1976193182A patent/PL110266B1/pl unknown
- 1976-10-21 NO NO763586A patent/NO145239C/no unknown
- 1976-10-21 GR GR51990A patent/GR72587B/el unknown
- 1976-10-21 DK DK475376A patent/DK475376A/da not_active Application Discontinuation
- 1976-10-21 YU YU02584/76A patent/YU258476A/xx unknown
- 1976-10-21 CA CA263,888A patent/CA1095060A/en not_active Expired
- 1976-10-22 JP JP51127127A patent/JPS5251399A/ja active Granted
-
1977
- 1977-03-15 FR FR7707631A patent/FR2329669A1/fr active Granted
- 1977-04-14 ES ES457808A patent/ES457808A1/es not_active Expired
-
1979
- 1979-06-25 US US06/051,499 patent/US4256642A/en not_active Expired - Lifetime
-
1985
- 1985-12-05 JP JP60272660A patent/JPS61218591A/ja active Pending
- 1985-12-05 JP JP60272661A patent/JPS61218583A/ja active Granted
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |