NO811229L - Fremgangsmaate ved fremstilling av nye tricykliske etere - Google Patents
Fremgangsmaate ved fremstilling av nye tricykliske etereInfo
- Publication number
- NO811229L NO811229L NO811229A NO811229A NO811229L NO 811229 L NO811229 L NO 811229L NO 811229 A NO811229 A NO 811229A NO 811229 A NO811229 A NO 811229A NO 811229 L NO811229 L NO 811229L
- Authority
- NO
- Norway
- Prior art keywords
- general formula
- derivative
- acid
- residue
- dibenzo
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 26
- 238000004519 manufacturing process Methods 0.000 title description 4
- 150000002170 ethers Chemical class 0.000 title description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 32
- 150000001875 compounds Chemical class 0.000 claims description 32
- 239000002253 acid Substances 0.000 claims description 19
- -1 trifluoromethyl- Chemical group 0.000 claims description 18
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 12
- QUSNBJAOOMFDIB-UHFFFAOYSA-N monoethyl amine Natural products CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 12
- 230000002829 reductive effect Effects 0.000 claims description 11
- 239000003795 chemical substances by application Substances 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- 125000004434 sulfur atom Chemical group 0.000 claims description 8
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 8
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 7
- 239000011707 mineral Substances 0.000 claims description 7
- 150000007524 organic acids Chemical class 0.000 claims description 7
- 150000001412 amines Chemical class 0.000 claims description 6
- 150000007522 mineralic acids Chemical class 0.000 claims description 6
- 230000003287 optical effect Effects 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 150000003462 sulfoxides Chemical class 0.000 claims description 5
- MLGQCJSEUUWVLJ-UHFFFAOYSA-N 2h-benzo[d][1]benzoxepin-1-one Chemical compound C12=CC=CC=C2C=COC2=C1C(=O)CC=C2 MLGQCJSEUUWVLJ-UHFFFAOYSA-N 0.000 claims description 4
- 239000005711 Benzoic acid Substances 0.000 claims description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 4
- 150000004678 hydrides Chemical class 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 150000003512 tertiary amines Chemical class 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052740 iodine Inorganic materials 0.000 claims description 3
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 3
- SPXRGBRACNDQPA-UHFFFAOYSA-N 2-phosphanylacetonitrile Chemical compound PCC#N SPXRGBRACNDQPA-UHFFFAOYSA-N 0.000 claims description 2
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims description 2
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 239000002168 alkylating agent Substances 0.000 claims description 2
- 230000002152 alkylating effect Effects 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 125000005530 alkylenedioxy group Chemical group 0.000 claims description 2
- 239000012435 aralkylating agent Substances 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 229910052728 basic metal Inorganic materials 0.000 claims description 2
- 150000003818 basic metals Chemical class 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 239000003638 chemical reducing agent Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 239000012024 dehydrating agents Substances 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
- 125000004464 hydroxyphenyl group Chemical group 0.000 claims description 2
- 239000013067 intermediate product Substances 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- 229910052987 metal hydride Inorganic materials 0.000 claims description 2
- 150000004681 metal hydrides Chemical class 0.000 claims description 2
- WDWDWGRYHDPSDS-UHFFFAOYSA-N methanimine Chemical compound N=C WDWDWGRYHDPSDS-UHFFFAOYSA-N 0.000 claims description 2
- 150000003335 secondary amines Chemical class 0.000 claims description 2
- 150000003457 sulfones Chemical class 0.000 claims description 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 235000005985 organic acids Nutrition 0.000 claims 1
- 239000007800 oxidant agent Substances 0.000 claims 1
- 238000007127 saponification reaction Methods 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 41
- 239000000243 solution Substances 0.000 description 40
- UZVGSSNIUNSOFA-UHFFFAOYSA-N dibenzofuran-1-carboxylic acid Chemical compound O1C2=CC=CC=C2C2=C1C=CC=C2C(=O)O UZVGSSNIUNSOFA-UHFFFAOYSA-N 0.000 description 34
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 29
- 239000000203 mixture Substances 0.000 description 28
- 239000000047 product Substances 0.000 description 25
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 22
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 20
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 15
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 11
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 9
- 239000000155 melt Substances 0.000 description 9
- 239000012071 phase Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 6
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 6
- 241000699670 Mus sp. Species 0.000 description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 6
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- KWTSXDURSIMDCE-QMMMGPOBSA-N (S)-amphetamine Chemical compound C[C@H](N)CC1=CC=CC=C1 KWTSXDURSIMDCE-QMMMGPOBSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 241000700159 Rattus Species 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 229940025084 amphetamine Drugs 0.000 description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- IWUQWGKADDZVKG-UHFFFAOYSA-N 3-(6h-benzo[b][1,4]benzodioxepin-6-yl)propan-1-amine Chemical compound NCCCC1OC2=CC=CC=C2OC2=CC=CC=C12 IWUQWGKADDZVKG-UHFFFAOYSA-N 0.000 description 3
- 206010001488 Aggression Diseases 0.000 description 3
- 206010010904 Convulsion Diseases 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 230000036461 convulsion Effects 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- XWBDWHCCBGMXKG-UHFFFAOYSA-N ethanamine;hydron;chloride Chemical compound Cl.CCN XWBDWHCCBGMXKG-UHFFFAOYSA-N 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 229960002523 mercuric chloride Drugs 0.000 description 3
- LWJROJCJINYWOX-UHFFFAOYSA-L mercury dichloride Chemical compound Cl[Hg]Cl LWJROJCJINYWOX-UHFFFAOYSA-L 0.000 description 3
- NAIDLBXXPCUDGF-UHFFFAOYSA-N methyl 2-benzo[b][1,4]benzodioxepin-6-ylideneacetate Chemical compound COC(=O)C=C1OC2=CC=CC=C2OC2=CC=CC=C12 NAIDLBXXPCUDGF-UHFFFAOYSA-N 0.000 description 3
- 235000010755 mineral Nutrition 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
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- 229910002027 silica gel Inorganic materials 0.000 description 3
- MKJIEFSOBYUXJB-HOCLYGCPSA-N (3S,11bS)-9,10-dimethoxy-3-isobutyl-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-2-one Chemical compound C1CN2C[C@H](CC(C)C)C(=O)C[C@H]2C2=C1C=C(OC)C(OC)=C2 MKJIEFSOBYUXJB-HOCLYGCPSA-N 0.000 description 2
- LBLYYCQCTBFVLH-UHFFFAOYSA-M 2-methylbenzenesulfonate Chemical compound CC1=CC=CC=C1S([O-])(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 description 2
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- 208000004130 Blepharoptosis Diseases 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 206010015995 Eyelid ptosis Diseases 0.000 description 2
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- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
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- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
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- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 235000011054 acetic acid Nutrition 0.000 description 2
- 230000001430 anti-depressive effect Effects 0.000 description 2
- 235000010233 benzoic acid Nutrition 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
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- 210000003169 central nervous system Anatomy 0.000 description 2
- 239000010779 crude oil Substances 0.000 description 2
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 2
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- SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 2
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- 239000000376 reactant Substances 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
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- PKIWRMJRXNMIOX-UHFFFAOYSA-N 2-(2,3-dichloro-6H-benzo[b][1,4]benzodioxepin-6-yl)ethanol Chemical compound OCCC1OC2=CC(Cl)=C(Cl)C=C2OC2=CC=CC=C12 PKIWRMJRXNMIOX-UHFFFAOYSA-N 0.000 description 1
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- QBUZVLCPPAHMJG-WLHGVMLRSA-N 2-(6h-benzo[b][1,4]benzodioxepin-6-yl)-n,n-diethylethanamine;(e)-but-2-enedioic acid Chemical compound OC(=O)\C=C\C(O)=O.CCN(CC)CCC1OC2=CC=CC=C2OC2=CC=CC=C12 QBUZVLCPPAHMJG-WLHGVMLRSA-N 0.000 description 1
- MBGLBBVRZGIUDD-UHFFFAOYSA-N 2-(6h-benzo[c][1,5]benzoxathiepin-6-yl)-n,n-diethylethanamine Chemical compound CCN(CC)CCC1OC2=CC=CC=C2SC2=CC=CC=C12 MBGLBBVRZGIUDD-UHFFFAOYSA-N 0.000 description 1
- GLCZOZSXSNORIE-UHFFFAOYSA-N 2-(9-chloro-6h-benzo[b][1,4]benzodioxepin-6-yl)ethanol Chemical compound OCCC1OC2=CC=CC=C2OC2=CC(Cl)=CC=C12 GLCZOZSXSNORIE-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- LCISFYAQKHOWBP-UHFFFAOYSA-N 2-chloro-5-(trifluoromethyl)benzonitrile Chemical compound FC(F)(F)C1=CC=C(Cl)C(C#N)=C1 LCISFYAQKHOWBP-UHFFFAOYSA-N 0.000 description 1
- HDECRAPHCDXMIJ-UHFFFAOYSA-N 2-methylbenzenesulfonyl chloride Chemical compound CC1=CC=CC=C1S(Cl)(=O)=O HDECRAPHCDXMIJ-UHFFFAOYSA-N 0.000 description 1
- PKRSYEPBQPFNRB-UHFFFAOYSA-N 2-phenoxybenzoic acid Chemical compound OC(=O)C1=CC=CC=C1OC1=CC=CC=C1 PKRSYEPBQPFNRB-UHFFFAOYSA-N 0.000 description 1
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- KRMDCWKBEZIMAB-UHFFFAOYSA-N amitriptyline Chemical compound C1CC2=CC=CC=C2C(=CCCN(C)C)C2=CC=CC=C21 KRMDCWKBEZIMAB-UHFFFAOYSA-N 0.000 description 1
- 229960000836 amitriptyline Drugs 0.000 description 1
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- 239000000935 antidepressant agent Substances 0.000 description 1
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- VMWNQDUVQKEIOC-CYBMUJFWSA-N apomorphine Chemical compound C([C@H]1N(C)CC2)C3=CC=C(O)C(O)=C3C3=C1C2=CC=C3 VMWNQDUVQKEIOC-CYBMUJFWSA-N 0.000 description 1
- 229960004046 apomorphine Drugs 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- OBKCQZVABDJKQE-UHFFFAOYSA-N dioxepin-3-one Chemical compound O=C1OOC=CC=C1 OBKCQZVABDJKQE-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- 208000013403 hyperactivity Diseases 0.000 description 1
- BCGWQEUPMDMJNV-UHFFFAOYSA-N imipramine Chemical compound C1CC2=CC=CC=C2N(CCCN(C)C)C2=CC=CC=C21 BCGWQEUPMDMJNV-UHFFFAOYSA-N 0.000 description 1
- 229960004801 imipramine Drugs 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000007928 intraperitoneal injection Substances 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- 229940045996 isethionic acid Drugs 0.000 description 1
- 230000002147 killing effect Effects 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 231100000636 lethal dose Toxicity 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 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
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- DMYPPMLNIYHBDT-UHFFFAOYSA-N methyl 2-(2,3-dichloro-6H-benzo[b][1,4]benzodioxepin-6-yl)acetate Chemical compound COC(=O)CC1OC2=CC(Cl)=C(Cl)C=C2OC2=CC=CC=C12 DMYPPMLNIYHBDT-UHFFFAOYSA-N 0.000 description 1
- BRAHSMNZDCTBHJ-UHFFFAOYSA-N methyl 2-(2,3-dichlorobenzo[b][1,4]benzodioxepin-6-ylidene)acetate Chemical compound COC(=O)C=C1OC2=CC(Cl)=C(Cl)C=C2OC2=CC=CC=C12 BRAHSMNZDCTBHJ-UHFFFAOYSA-N 0.000 description 1
- HMVCQOFDKHMSOV-UHFFFAOYSA-N methyl 2-(3-chlorobenzo[b][1,4]benzodioxepin-6-ylidene)acetate Chemical compound COC(=O)C=C1OC2=CC(Cl)=CC=C2OC2=CC=CC=C12 HMVCQOFDKHMSOV-UHFFFAOYSA-N 0.000 description 1
- GUCDXXIQSCWVKM-UHFFFAOYSA-N methyl 2-(9-chloro-6h-benzo[b][1,4]benzodioxepin-6-yl)acetate Chemical compound COC(=O)CC1OC2=CC=CC=C2OC2=CC(Cl)=CC=C12 GUCDXXIQSCWVKM-UHFFFAOYSA-N 0.000 description 1
- VDRCAKUKSCRBGK-UHFFFAOYSA-N methyl 2-(9-chlorobenzo[b][1,4]benzodioxepin-6-ylidene)acetate Chemical compound COC(=O)C=C1OC2=CC=CC=C2OC2=CC(Cl)=CC=C12 VDRCAKUKSCRBGK-UHFFFAOYSA-N 0.000 description 1
- GMLVWPAPYUULKJ-UHFFFAOYSA-N methyl 2-benzo[b][1,5]benzoxathiepin-6-ylideneacetate Chemical compound COC(=O)C=C1SC2=CC=CC=C2OC2=CC=CC=C12 GMLVWPAPYUULKJ-UHFFFAOYSA-N 0.000 description 1
- 229960003955 mianserin Drugs 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 231100000957 no side effect Toxicity 0.000 description 1
- 210000000956 olfactory bulb Anatomy 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 230000000506 psychotropic effect Effects 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 229940107700 pyruvic acid Drugs 0.000 description 1
- BJOIZNZVOZKDIG-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C([C]5C=CC(OC)=CC5=N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 BJOIZNZVOZKDIG-MDEJGZGSSA-N 0.000 description 1
- 229960003147 reserpine Drugs 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- MDMGHDFNKNZPAU-UHFFFAOYSA-N roserpine Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(OC(C)=O)C(OC)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 MDMGHDFNKNZPAU-UHFFFAOYSA-N 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D321/00—Heterocyclic compounds containing rings having two oxygen atoms as the only ring hetero atoms, not provided for by groups C07D317/00 - C07D319/00
- C07D321/02—Seven-membered rings
- C07D321/10—Seven-membered rings condensed with carbocyclic rings or ring 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
-
- 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
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
-
- 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
- A61P25/08—Antiepileptics; Anticonvulsants
-
- 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
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- 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
-
- 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
- A61P25/24—Antidepressants
-
- 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
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D327/00—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms
- C07D327/02—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms one oxygen atom and one sulfur atom
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Neurosurgery (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biomedical Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Neurology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Anesthesiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8008023A FR2480283A1 (fr) | 1980-04-10 | 1980-04-10 | Nouveaux derives tricycliques, leurs procedes de preparation et leur utilisation comme medicament |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO811229L true NO811229L (no) | 1981-10-12 |
Family
ID=9240699
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO811229A NO811229L (no) | 1980-04-10 | 1981-04-09 | Fremgangsmaate ved fremstilling av nye tricykliske etere |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US4459306A (zh) |
| EP (1) | EP0041410B1 (zh) |
| JP (1) | JPS56158780A (zh) |
| AR (1) | AR229026A1 (zh) |
| AT (1) | ATE5257T1 (zh) |
| AU (1) | AU538054B2 (zh) |
| CA (1) | CA1181068A (zh) |
| DD (1) | DD158242A5 (zh) |
| DE (1) | DE3161358D1 (zh) |
| DK (1) | DK159981A (zh) |
| ES (2) | ES8306483A1 (zh) |
| FI (1) | FI811059L (zh) |
| FR (1) | FR2480283A1 (zh) |
| GR (1) | GR75194B (zh) |
| IL (1) | IL62622A (zh) |
| MA (1) | MA19113A1 (zh) |
| NO (1) | NO811229L (zh) |
| NZ (1) | NZ196774A (zh) |
| OA (1) | OA06779A (zh) |
| PT (1) | PT72833B (zh) |
| SU (1) | SU1106444A3 (zh) |
| YU (1) | YU92481A (zh) |
| ZA (1) | ZA812379B (zh) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2094790B (en) * | 1981-03-13 | 1985-10-09 | Spofa Vereinigte Pharma Werke | Tricycle compounds |
| CA1208653A (en) * | 1982-09-30 | 1986-07-29 | Pierre Hamel | 6h-dibenz [b,e] [1,4] oxathiepin derivatives |
| DE69502939T2 (de) * | 1994-03-02 | 1998-10-22 | Akzo Nobel Nv | Sublinguales oder bukkales arzneimittel |
| JP4006796B2 (ja) | 1997-11-17 | 2007-11-14 | 株式会社日立製作所 | 個人情報管理方法および装置 |
| ATE445838T1 (de) | 2001-07-25 | 2009-10-15 | Raptor Pharmaceutical Inc | Zusammensetzungen und verfahren zur modulation des transports durch die blut-hirn-schranke |
| US6683072B1 (en) | 2003-02-04 | 2004-01-27 | Vela Pharmaceuticals, Inc. | Compositions and methods for treatment of irritable bowel syndrome and nonulcer dyspepsia |
| US20050227961A1 (en) * | 2004-04-08 | 2005-10-13 | Vela Pharmaceuticals, Inc. | Compositions and methods for treatment of neuropathic pain, fibromyalgia and chronic fatigue syndrome |
| EP2671508B1 (en) | 2005-04-28 | 2020-09-16 | Proteus Digital Health, Inc. | Pharma-informatics system |
| CA2663377A1 (en) | 2006-09-18 | 2008-03-27 | Raptor Pharmaceutical Inc. | Treatment of liver disorders by administration of receptor-associated protein (rap)-conjugates |
| HUE059078T2 (hu) | 2009-02-20 | 2022-10-28 | Enhanx Biopharm Inc | Glutation-alapú hatóanyagszállító rendszer |
| JP2012526144A (ja) | 2009-05-06 | 2012-10-25 | ラボラトリー スキン ケア インコーポレイテッド | 活性物質−リン酸カルシウム粒子複合体を含む経皮送達組成物およびその使用方法 |
| US20120077778A1 (en) | 2010-09-29 | 2012-03-29 | Andrea Bourdelais | Ladder-Frame Polyether Conjugates |
| CN111377901A (zh) * | 2018-12-27 | 2020-07-07 | 华东理工大学 | 一种缩酚酸环醚类化合物及其制备方法与用途 |
| CN117279632A (zh) * | 2021-04-10 | 2023-12-22 | 赛诺维信制药公司 | Taar1和血清素调节剂、及其医药组合物、及使用方法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE613212A (fr) * | 1961-01-30 | 1962-07-30 | Geigy Ag J R | Nouveaux 1.5-benzo-dioxépannes et leur préparation |
| FR1312891A (fr) * | 1962-01-29 | 1962-12-21 | Geigy Ag J R | Nouveaux 1.5-benzo-dioxépannes et leur préparation |
| FR1312889A (fr) * | 1962-01-29 | 1962-12-21 | Geigy Ag J R | Nouveaux benzo-dioxépannes et leur préparation |
| US3758528A (en) * | 1970-03-13 | 1973-09-11 | Science Union & Cie | Tricyclic compounds |
| US3821249A (en) * | 1970-03-13 | 1974-06-28 | En Nom Collectif Science Union | Dibenzothiazefin derivatives |
| US4039676A (en) * | 1975-06-23 | 1977-08-02 | Ciba-Geigy Corporation | 2-piperidinoalkyl-1,4-benzodioxans |
| US4335122A (en) * | 1981-03-18 | 1982-06-15 | Hoechst-Roussel Pharmaceuticals Inc. | Dihydro-dibenzoxepines-thiepines and -morphanthridones, compositions and use |
-
1980
- 1980-04-10 FR FR8008023A patent/FR2480283A1/fr active Granted
-
1981
- 1981-03-31 ES ES500942A patent/ES8306483A1/es not_active Expired
- 1981-04-03 MA MA19318A patent/MA19113A1/fr unknown
- 1981-04-06 US US06/251,052 patent/US4459306A/en not_active Expired - Fee Related
- 1981-04-06 CA CA000374790A patent/CA1181068A/fr not_active Expired
- 1981-04-06 FI FI811059A patent/FI811059L/fi not_active Application Discontinuation
- 1981-04-07 DE DE8181400551T patent/DE3161358D1/de not_active Expired
- 1981-04-07 EP EP81400551A patent/EP0041410B1/fr not_active Expired
- 1981-04-07 AT AT81400551T patent/ATE5257T1/de not_active IP Right Cessation
- 1981-04-08 GR GR64621A patent/GR75194B/el unknown
- 1981-04-09 ZA ZA00812379A patent/ZA812379B/xx unknown
- 1981-04-09 JP JP5374381A patent/JPS56158780A/ja active Granted
- 1981-04-09 PT PT72833A patent/PT72833B/pt unknown
- 1981-04-09 DK DK159981A patent/DK159981A/da not_active IP Right Cessation
- 1981-04-09 NZ NZ196774A patent/NZ196774A/xx unknown
- 1981-04-09 NO NO811229A patent/NO811229L/no unknown
- 1981-04-09 AU AU69340/81A patent/AU538054B2/en not_active Ceased
- 1981-04-09 SU SU813269597A patent/SU1106444A3/ru active
- 1981-04-09 IL IL62622A patent/IL62622A/xx unknown
- 1981-04-09 AR AR284911A patent/AR229026A1/es active
- 1981-04-09 YU YU00924/81A patent/YU92481A/xx unknown
- 1981-04-10 OA OA57367A patent/OA06779A/xx unknown
- 1981-04-10 DD DD81229155A patent/DD158242A5/de unknown
-
1983
- 1983-02-01 ES ES519463A patent/ES8400742A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DD158242A5 (de) | 1983-01-05 |
| DE3161358D1 (en) | 1983-12-15 |
| FR2480283B1 (zh) | 1983-09-23 |
| ZA812379B (en) | 1982-04-28 |
| ATE5257T1 (de) | 1983-11-15 |
| EP0041410A1 (fr) | 1981-12-09 |
| FI811059L (fi) | 1981-10-11 |
| JPS6116394B2 (zh) | 1986-04-30 |
| IL62622A (en) | 1984-10-31 |
| ES519463A0 (es) | 1983-11-16 |
| AR229026A1 (es) | 1983-05-31 |
| CA1181068A (fr) | 1985-01-15 |
| YU92481A (en) | 1984-02-29 |
| ES500942A0 (es) | 1983-06-01 |
| SU1106444A3 (ru) | 1984-07-30 |
| PT72833A (fr) | 1981-05-01 |
| MA19113A1 (fr) | 1981-12-31 |
| IL62622A0 (en) | 1981-06-29 |
| DK159981A (da) | 1981-10-11 |
| US4459306A (en) | 1984-07-10 |
| NZ196774A (en) | 1983-09-30 |
| GR75194B (zh) | 1984-07-13 |
| EP0041410B1 (fr) | 1983-11-09 |
| ES8400742A1 (es) | 1983-11-16 |
| AU538054B2 (en) | 1984-07-26 |
| JPS56158780A (en) | 1981-12-07 |
| OA06779A (fr) | 1982-12-31 |
| FR2480283A1 (fr) | 1981-10-16 |
| AU6934081A (en) | 1981-10-15 |
| ES8306483A1 (es) | 1983-06-01 |
| PT72833B (fr) | 1982-07-26 |
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