IL44145A - Dioxatricyclodecanes and their production - Google Patents
Dioxatricyclodecanes and their productionInfo
- Publication number
- IL44145A IL44145A IL44145A IL4414574A IL44145A IL 44145 A IL44145 A IL 44145A IL 44145 A IL44145 A IL 44145A IL 4414574 A IL4414574 A IL 4414574A IL 44145 A IL44145 A IL 44145A
- Authority
- IL
- Israel
- Prior art keywords
- general formula
- hydroxy
- dioxatricyclo
- hydrogenated
- hydrogen atom
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 16
- 150000002148 esters Chemical class 0.000 claims abstract description 15
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 14
- 238000000034 method Methods 0.000 claims abstract description 7
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims abstract description 6
- KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 claims abstract description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims abstract description 4
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 4
- 150000001412 amines Chemical class 0.000 claims abstract description 4
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 claims abstract description 4
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 4
- 239000012948 isocyanate Substances 0.000 claims abstract description 4
- 150000002513 isocyanates Chemical class 0.000 claims abstract description 4
- 229910052987 metal hydride Inorganic materials 0.000 claims abstract description 3
- 150000004681 metal hydrides Chemical class 0.000 claims abstract description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims abstract 3
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 claims description 44
- 125000004432 carbon atom Chemical group C* 0.000 claims description 16
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- -1 chloroformic acid ester Chemical class 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims 2
- 239000004215 Carbon black (E152) Substances 0.000 claims 1
- JDPQWHLMBJZURR-UHFFFAOYSA-N decan-5-one Chemical compound CCCCCC(=O)CCCC JDPQWHLMBJZURR-UHFFFAOYSA-N 0.000 claims 1
- 229930195733 hydrocarbon Natural products 0.000 claims 1
- ZAJNGDIORYACQU-UHFFFAOYSA-N methyl n-octyl ketone Natural products CCCCCCCCC(C)=O ZAJNGDIORYACQU-UHFFFAOYSA-N 0.000 claims 1
- 230000003533 narcotic effect Effects 0.000 abstract description 11
- 239000000932 sedative agent Substances 0.000 abstract description 6
- 239000000203 mixture Substances 0.000 abstract description 5
- 239000001257 hydrogen Substances 0.000 abstract description 4
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 4
- 230000001624 sedative effect Effects 0.000 abstract description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract description 2
- 239000000460 chlorine Substances 0.000 abstract description 2
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 abstract 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 45
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 38
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 14
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- 208000010513 Stupor Diseases 0.000 description 10
- 230000000694 effects Effects 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 229960000583 acetic acid Drugs 0.000 description 6
- 150000001298 alcohols Chemical class 0.000 description 5
- UYXAWHWODHRRMR-UHFFFAOYSA-N hexobarbital Chemical compound O=C1N(C)C(=O)NC(=O)C1(C)C1=CCCCC1 UYXAWHWODHRRMR-UHFFFAOYSA-N 0.000 description 5
- 229960002456 hexobarbital Drugs 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- HXBPYFMVGFDZFT-UHFFFAOYSA-N allyl isocyanate Chemical compound C=CCN=C=O HXBPYFMVGFDZFT-UHFFFAOYSA-N 0.000 description 4
- 229940125717 barbiturate Drugs 0.000 description 4
- 239000012362 glacial acetic acid Substances 0.000 description 4
- 239000003326 hypnotic agent Substances 0.000 description 4
- 230000000147 hypnotic effect Effects 0.000 description 4
- 239000005457 ice water Substances 0.000 description 4
- 229910052938 sodium sulfate Inorganic materials 0.000 description 4
- 235000011152 sodium sulphate Nutrition 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 206010003591 Ataxia Diseases 0.000 description 3
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 230000000994 depressogenic effect Effects 0.000 description 3
- 230000032050 esterification Effects 0.000 description 3
- 238000005886 esterification reaction Methods 0.000 description 3
- 239000012259 ether extract Substances 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- GSLTVFIVJMCNBH-UHFFFAOYSA-N 2-isocyanatopropane Chemical compound CC(C)N=C=O GSLTVFIVJMCNBH-UHFFFAOYSA-N 0.000 description 2
- UWDMKTDPDJCJOP-UHFFFAOYSA-N 4-hydroxy-2,2,6,6-tetramethylpiperidin-1-ium-4-carboxylate Chemical compound CC1(C)CC(O)(C(O)=O)CC(C)(C)N1 UWDMKTDPDJCJOP-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 241000282472 Canis lupus familiaris Species 0.000 description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
- 241000282326 Felis catus Species 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 210000003169 central nervous system Anatomy 0.000 description 2
- 229940112021 centrally acting muscle relaxants carbamic acid ester Drugs 0.000 description 2
- 239000003610 charcoal Substances 0.000 description 2
- KQWGXHWJMSMDJJ-UHFFFAOYSA-N cyclohexyl isocyanate Chemical compound O=C=NC1CCCCC1 KQWGXHWJMSMDJJ-UHFFFAOYSA-N 0.000 description 2
- WUDNUHPRLBTKOJ-UHFFFAOYSA-N ethyl isocyanate Chemical compound CCN=C=O WUDNUHPRLBTKOJ-UHFFFAOYSA-N 0.000 description 2
- 230000002045 lasting effect Effects 0.000 description 2
- 239000004081 narcotic agent Substances 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 238000006722 reduction reaction Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- BIIBYWQGRFWQKM-JVVROLKMSA-N (2S)-N-[4-(cyclopropylamino)-3,4-dioxo-1-[(3S)-2-oxopyrrolidin-3-yl]butan-2-yl]-2-[[(E)-3-(2,4-dichlorophenyl)prop-2-enoyl]amino]-4,4-dimethylpentanamide Chemical compound CC(C)(C)C[C@@H](C(NC(C[C@H](CCN1)C1=O)C(C(NC1CC1)=O)=O)=O)NC(/C=C/C(C=CC(Cl)=C1)=C1Cl)=O BIIBYWQGRFWQKM-JVVROLKMSA-N 0.000 description 1
- KNTZCGBYFGEMFR-UHFFFAOYSA-N (propan-2-ylazaniumyl)formate Chemical compound CC(C)NC(O)=O KNTZCGBYFGEMFR-UHFFFAOYSA-N 0.000 description 1
- DFGKGUXTPFWHIX-UHFFFAOYSA-N 6-[2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]acetyl]-3H-1,3-benzoxazol-2-one Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)CC(=O)C1=CC2=C(NC(O2)=O)C=C1 DFGKGUXTPFWHIX-UHFFFAOYSA-N 0.000 description 1
- 229930003347 Atropine Natural products 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- RKUNBYITZUJHSG-UHFFFAOYSA-N Hyosciamin-hydrochlorid Natural products CN1C(C2)CCC1CC2OC(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- 239000004411 aluminium Substances 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
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 239000001166 ammonium sulphate Substances 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 230000002082 anti-convulsion Effects 0.000 description 1
- RKUNBYITZUJHSG-SPUOUPEWSA-N atropine Chemical compound O([C@H]1C[C@H]2CC[C@@H](C1)N2C)C(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-SPUOUPEWSA-N 0.000 description 1
- 229960000396 atropine Drugs 0.000 description 1
- HNYOPLTXPVRDBG-UHFFFAOYSA-M barbiturate Chemical compound O=C1CC(=O)[N-]C(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-M 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000036983 biotransformation Effects 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 238000010531 catalytic reduction reaction Methods 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000000812 cholinergic antagonist Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- KWBIXTIBYFUAGV-UHFFFAOYSA-N ethylcarbamic acid Chemical compound CCNC(O)=O KWBIXTIBYFUAGV-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 231100000171 higher toxicity Toxicity 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000005554 hypnotics and sedatives Substances 0.000 description 1
- 229940005535 hypnotics and sedatives Drugs 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 231100000636 lethal dose Toxicity 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 230000036225 muscular coordination Effects 0.000 description 1
- 210000000653 nervous system Anatomy 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- DDBREPKUVSBGFI-UHFFFAOYSA-N phenobarbital Chemical compound C=1C=CC=CC=1C1(CC)C(=O)NC(=O)NC1=O DDBREPKUVSBGFI-UHFFFAOYSA-N 0.000 description 1
- 229960002695 phenobarbital Drugs 0.000 description 1
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 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
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000002040 relaxant effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000000241 respiratory effect Effects 0.000 description 1
- LMHHRCOWPQNFTF-UHFFFAOYSA-N s-propan-2-yl azepane-1-carbothioate Chemical compound CC(C)SC(=O)N1CCCCCC1 LMHHRCOWPQNFTF-UHFFFAOYSA-N 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 229940125723 sedative agent Drugs 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000002048 spasmolytic effect Effects 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 239000003071 vasodilator agent Substances 0.000 description 1
- 230000001457 vasomotor Effects 0.000 description 1
- 238000005406 washing Methods 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
- A61P23/00—Anaesthetics
-
- 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
- A61P25/20—Hypnotics; Sedatives
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Anesthesiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2306118A DE2306118C3 (de) | 1973-02-08 | 1973-02-08 | S-Methyl-lO-methylen^-dioxatricyclo [43,1,037I decane und 3,10-Dimethyl2,9-dioxatricyclo [43,1, 03·7! decane sowie Verfahren zu deren Herstellung |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL44145A0 IL44145A0 (en) | 1974-05-16 |
| IL44145A true IL44145A (en) | 1977-06-30 |
Family
ID=5871280
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL44145A IL44145A (en) | 1973-02-08 | 1974-02-05 | Dioxatricyclodecanes and their production |
Country Status (20)
| Country | Link |
|---|---|
| JP (1) | JPS5750793B2 (de) |
| AT (1) | AT332397B (de) |
| BE (1) | BE810475A (de) |
| CA (1) | CA1025873A (de) |
| CH (1) | CH603657A5 (de) |
| CS (1) | CS175472B2 (de) |
| DD (1) | DD109872A5 (de) |
| ES (1) | ES422841A1 (de) |
| FI (1) | FI56533C (de) |
| FR (1) | FR2217008B1 (de) |
| GB (1) | GB1436821A (de) |
| HU (1) | HU169556B (de) |
| IE (1) | IE38815B1 (de) |
| IL (1) | IL44145A (de) |
| NL (1) | NL183011C (de) |
| NO (1) | NO140981C (de) |
| PH (1) | PH12696A (de) |
| SE (1) | SE403115B (de) |
| SU (4) | SU576939A3 (de) |
| ZA (1) | ZA74845B (de) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| RU2494102C1 (ru) * | 2012-08-15 | 2013-09-27 | ФЕДЕРАЛЬНОЕ ГОСУДАРСТВЕННОЕ БЮДЖЕТНОЕ УЧРЕЖДЕНИЕ НАУКИ ИНСТИТУТ ОРГАНИЧЕСКОЙ ХИМИИ им. Н.Д. ЗЕЛИНСКОГО РОССИЙСКОЙ АКАДЕМИИ НАУК (ИОХ РАН) | Способ получения замещенных 2,3,5,6-тетраоксабицикло[2.2.1]гептанов |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2027890C3 (de) * | 1970-06-06 | 1979-02-01 | Kali Chemie Ag | 8-AIkoxy oder -Benzyloxy-3-methyl-lO- methylen-2,9-dioxatricyclo-(43,l,03,7 )-decan-4-one und 8-AIkoxy oder 8-Benzyloxy-3,10-dimethyl-2,9dioxatricyclo- (43,1,O" )-decan-4-one |
| DE2129507C3 (de) * | 1971-06-15 | 1980-02-14 | Kali-Chemie Ag, 3000 Hannover | Verfahren zur Herstellung von 8-Alkoxy-3halogenmethyl-4-acetoxy- 10-methylen-2,9dioxatricyclo(43,l,03 7 )decanen |
-
1973
- 1973-12-27 FI FI3983/73A patent/FI56533C/fi active
-
1974
- 1974-01-08 CH CH19374A patent/CH603657A5/xx not_active IP Right Cessation
- 1974-01-11 NL NLAANVRAGE7400404,A patent/NL183011C/xx not_active IP Right Cessation
- 1974-01-18 GB GB254874A patent/GB1436821A/en not_active Expired
- 1974-01-31 BE BE140441A patent/BE810475A/xx not_active IP Right Cessation
- 1974-02-01 ES ES422841A patent/ES422841A1/es not_active Expired
- 1974-02-04 IE IE196/74A patent/IE38815B1/xx unknown
- 1974-02-05 IL IL44145A patent/IL44145A/en unknown
- 1974-02-05 HU HUKA1402A patent/HU169556B/hu unknown
- 1974-02-05 JP JP49014830A patent/JPS5750793B2/ja not_active Expired
- 1974-02-06 CS CS815A patent/CS175472B2/cs unknown
- 1974-02-06 DD DD176411A patent/DD109872A5/xx unknown
- 1974-02-07 FR FR7404118A patent/FR2217008B1/fr not_active Expired
- 1974-02-07 AT AT97574*#A patent/AT332397B/de not_active IP Right Cessation
- 1974-02-07 SE SE7401645A patent/SE403115B/xx unknown
- 1974-02-07 SU SU7401998126A patent/SU576939A3/ru active
- 1974-02-07 NO NO740403A patent/NO140981C/no unknown
- 1974-02-08 CA CA192,121A patent/CA1025873A/en not_active Expired
- 1974-02-08 PH PH15490A patent/PH12696A/en unknown
- 1974-02-08 ZA ZA00740845A patent/ZA74845B/xx unknown
-
1975
- 1975-03-03 SU SU752109640A patent/SU659086A3/ru active
- 1975-04-09 SU SU752121560A patent/SU648562A1/ru active
-
1976
- 1976-04-21 SU SU762347297A patent/SU643503A1/ru active
Also Published As
| Publication number | Publication date |
|---|---|
| CH603657A5 (de) | 1978-08-31 |
| AU6522174A (en) | 1975-08-07 |
| HU169556B (de) | 1976-12-28 |
| SU648562A1 (en) | 1979-02-25 |
| FI56533C (fi) | 1980-02-11 |
| JPS49109397A (de) | 1974-10-17 |
| SU643503A1 (ru) | 1979-01-25 |
| PH12696A (en) | 1979-07-18 |
| CS175472B2 (de) | 1977-05-31 |
| GB1436821A (en) | 1976-05-26 |
| JPS5750793B2 (de) | 1982-10-28 |
| SU659086A3 (ru) | 1979-04-25 |
| AT332397B (de) | 1976-09-27 |
| NO140981B (no) | 1979-09-10 |
| ES422841A1 (es) | 1976-05-01 |
| DD109872A5 (de) | 1974-11-20 |
| ZA74845B (en) | 1975-01-29 |
| FR2217008A1 (de) | 1974-09-06 |
| CA1025873A (en) | 1978-02-07 |
| NL183011B (nl) | 1988-02-01 |
| BE810475A (fr) | 1974-05-16 |
| IL44145A0 (en) | 1974-05-16 |
| NL183011C (nl) | 1988-07-01 |
| SU576939A3 (ru) | 1977-10-15 |
| ATA97574A (de) | 1976-01-15 |
| NO740403L (no) | 1974-08-09 |
| IE38815L (en) | 1974-08-08 |
| IE38815B1 (en) | 1978-06-07 |
| FI56533B (fi) | 1979-10-31 |
| NO140981C (no) | 1979-12-19 |
| SE403115B (sv) | 1978-07-31 |
| NL7400404A (de) | 1974-08-12 |
| FR2217008B1 (de) | 1977-11-10 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0079022B1 (de) | Derivate der cis, endo-2-Azabicyclo-(3.3.0)-octan-3-carbonsäure, Verfahren zu ihrer Herstellung, diese enthaltende Mittel und deren Verwendung | |
| EP1226110B1 (de) | Bicyclische aminosäuren als pharmazeutische mittel | |
| JP2002516312A (ja) | カルシウムチャンネルのα２δサブユニットに対する親和性を有する立体配座的に制約されたアミノ酸化合物 | |
| US4282248A (en) | Pinene derivatives and pharmaceutical compositions containing the same | |
| EP0109020A2 (de) | Neue Derivate tricyclischer Aminosäuren, Verfahren zu ihrer Herstellung, diese enthaltende Mittel und deren Verwendung, sowie neue bicyclische Aminosäuren als Zwischenstufen und Verfahren zu deren Herstellung | |
| CH651561A5 (fr) | Derives des nor-tropane et granatane et leur procede de preparation. | |
| CH631696A5 (de) | Verfahren zur herstellung von olefinischen derivaten von aminosaeuren. | |
| DE60012888T2 (de) | Mevinolinderivate | |
| EP0116276A2 (de) | Neue spirocyclische Aminosäurederivate, Verfahren zu ihrer Herstellung, diese enthaltende Mittel und deren Verwendung sowie neue spirocyclische Aminosäuren als Zwischenprodukte und Verfahren zu deren Herstellung | |
| DE3300316A1 (de) | Disubstituierte prolinderivate, verfahren zu ihrer herstellung und ihre verwendung | |
| EP0280269A1 (de) | 3-Amino-dihydro-[1]-benzopyrane und Benzothiopyrane | |
| EP0026369B1 (de) | Neue Carbamate, ihre Herstellung und diese enthaltende pharmazeutische Zubereitungen | |
| IL44145A (en) | Dioxatricyclodecanes and their production | |
| EP0657455A1 (de) | Epi-epibatidinederivate, Verfahren und Zwischenprodukte für ihre Herstellung und Epi-epibatidine und die Epi-epibatidinederivate enthaltende Arzneimittel und/oder Epi-epibatidine und ihre Verwendung | |
| JPS58170724A (ja) | 置換ヘキサヒドロピロロ［１，２―ａ］キノリンおよびヘキサヒドロ―１Ｈ―ピリド―［１，２―ａ］キノリン化合物 | |
| EP0009777A1 (de) | Retinsäure- und 7,8-Dehydro-retinsäure-N-(carboxy)-phenyl-amide, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Mittel | |
| DE60112917T2 (de) | Neue polyzyklische indanylimidazole mit alpha2 adrenergik aktivität | |
| US4016176A (en) | Esters of 4-hydroxy-2,9-dioxatricyclo[4.3.1.03,7 ] decanes and processes for their production | |
| US4256642A (en) | Pharmaceutically active 2,9-dioxatricyclo[4,3,1,03,7 ] decanes | |
| DD202541A5 (de) | Verfahren zur herstellung neuer indol-derivate | |
| EP0113880A2 (de) | Neue 2-Azabicyclo(2.2.1)heptan-Derivate, Verfahren zu ihrer Herstellung, diese enthaltende Mittel und deren Verwendung sowie 2-Azabicyclo(2.2.1)heptan-Derivate als Zwischenprodukte und Verfahren zu deren Herstellung | |
| AT234103B (de) | Verfahren zur Herstellung von neuen, benzylindolylsubstituierten niedrigen aliphatischen Säuren sowie deren Salzen und Estern | |
| US4029647A (en) | Synthesis of biotin | |
| CH638213A5 (de) | Verfahren zur herstellung von 2,9-dioxatricyclo-(4,3,1,03,7)-decanen. | |
| Keana et al. | Synthetic intermediates potentially useful for the synthesis of tetrodotoxin and derivatives. II. Reaction of diazomethane with some shikimic acid derivatives |