NO121457B - - Google Patents
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- Publication number
- NO121457B NO121457B NO1649/69A NO164969A NO121457B NO 121457 B NO121457 B NO 121457B NO 1649/69 A NO1649/69 A NO 1649/69A NO 164969 A NO164969 A NO 164969A NO 121457 B NO121457 B NO 121457B
- Authority
- NO
- Norway
- Prior art keywords
- lysergic acid
- acid
- mixed anhydride
- approx
- dimethylformamide
- Prior art date
Links
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 75
- ZAGRKAFMISFKIO-UHFFFAOYSA-N Isolysergic acid Natural products C1=CC(C2=CC(CN(C2C2)C)C(O)=O)=C3C2=CNC3=C1 ZAGRKAFMISFKIO-UHFFFAOYSA-N 0.000 claims description 65
- 150000008064 anhydrides Chemical class 0.000 claims description 65
- ZAGRKAFMISFKIO-QMTHXVAHSA-N lysergic acid Chemical compound C1=CC(C2=C[C@H](CN([C@@H]2C2)C)C(O)=O)=C3C2=CNC3=C1 ZAGRKAFMISFKIO-QMTHXVAHSA-N 0.000 claims description 65
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 claims description 60
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 45
- 238000000034 method Methods 0.000 claims description 38
- 150000001408 amides Chemical class 0.000 claims description 19
- 150000001875 compounds Chemical class 0.000 claims description 19
- 229960001405 ergometrine Drugs 0.000 claims description 18
- GENAHGKEFJLNJB-QMTHXVAHSA-N lysergamide Chemical compound C1=CC(C2=C[C@H](CN([C@@H]2C2)C)C(N)=O)=C3C2=CNC3=C1 GENAHGKEFJLNJB-QMTHXVAHSA-N 0.000 claims description 17
- WVVSZNPYNCNODU-CJBNDPTMSA-N Ergometrine Natural products C1=CC(C=2[C@H](N(C)C[C@@H](C=2)C(=O)N[C@@H](CO)C)C2)=C3C2=CNC3=C1 WVVSZNPYNCNODU-CJBNDPTMSA-N 0.000 claims description 16
- WVVSZNPYNCNODU-XTQGRXLLSA-N Lysergic acid propanolamide Chemical compound C1=CC(C=2[C@H](N(C)C[C@@H](C=2)C(=O)N[C@H](CO)C)C2)=C3C2=CNC3=C1 WVVSZNPYNCNODU-XTQGRXLLSA-N 0.000 claims description 16
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 16
- 239000002270 dispersing agent Substances 0.000 claims description 13
- 238000004519 manufacturing process Methods 0.000 claims description 11
- 239000006185 dispersion Substances 0.000 claims description 6
- AFDQGRURHDVABZ-UHFFFAOYSA-N n,n-dimethylformamide;sulfur trioxide Chemical compound O=S(=O)=O.CN(C)C=O AFDQGRURHDVABZ-UHFFFAOYSA-N 0.000 claims description 6
- 150000001447 alkali salts Chemical class 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- 150000001414 amino alcohols Chemical class 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- 229910003002 lithium salt Inorganic materials 0.000 claims description 3
- 159000000002 lithium salts Chemical class 0.000 claims description 3
- 150000003141 primary amines Chemical class 0.000 claims description 2
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 claims 1
- 239000000243 solution Substances 0.000 description 47
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 34
- 239000000203 mixture Substances 0.000 description 30
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 17
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- 239000002585 base Substances 0.000 description 15
- 150000003839 salts Chemical class 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 14
- -1 lysergic acid compound Chemical class 0.000 description 12
- 238000002360 preparation method Methods 0.000 description 12
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 11
- 239000006188 syrup Substances 0.000 description 11
- 235000020357 syrup Nutrition 0.000 description 11
- 239000002253 acid Substances 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 10
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 10
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 9
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical class [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 8
- 239000011591 potassium Chemical class 0.000 description 8
- 229910052700 potassium Inorganic materials 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
- 239000013078 crystal Substances 0.000 description 7
- 239000000284 extract Substances 0.000 description 7
- 239000000706 filtrate Substances 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- VAPRZIDWFJHKLR-BWTUWSSMSA-N (6ar,9r)-7-methyl-6,6a,8,9-tetrahydro-4h-indolo[4,3-fg]quinoline-9-carboxylic acid;hydrate Chemical compound O.C1=CC(C2=C[C@H](CN([C@@H]2C2)C)C(O)=O)=C3C2=CNC3=C1 VAPRZIDWFJHKLR-BWTUWSSMSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- 238000001704 evaporation Methods 0.000 description 6
- 230000008020 evaporation Effects 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- ZAGRKAFMISFKIO-IINYFYTJSA-N (6ar,9s)-7-methyl-6,6a,8,9-tetrahydro-4h-indolo[4,3-fg]quinoline-9-carboxylic acid Chemical compound C1=CC(C2=C[C@@H](CN([C@@H]2C2)C)C(O)=O)=C3C2=CNC3=C1 ZAGRKAFMISFKIO-IINYFYTJSA-N 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 239000011976 maleic acid Substances 0.000 description 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- SRYBEKTWSIQBOV-IIBYNOLFSA-N CN1C[C@@H](C=C2[C@H]1CC3=CNC4=CC=CC2=C34)C(=O)N(C)C5=CC=CC=C5 Chemical compound CN1C[C@@H](C=C2[C@H]1CC3=CNC4=CC=CC2=C34)C(=O)N(C)C5=CC=CC=C5 SRYBEKTWSIQBOV-IIBYNOLFSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
- 239000000908 ammonium hydroxide Substances 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- GENAHGKEFJLNJB-UHFFFAOYSA-N Lysergsaeure-amid Natural products C1=CC(C2=CC(CN(C2C2)C)C(N)=O)=C3C2=CNC3=C1 GENAHGKEFJLNJB-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- OTQWCDNEJVKXKG-RDTXWAMCSA-N [(6ar,9r)-7-methyl-6,6a,8,9-tetrahydro-4h-indolo[4,3-fg]quinoline-9-yl]-morpholin-4-ylmethanone Chemical compound O=C([C@H]1CN([C@H]2C(C=3C=CC=C4NC=C(C=34)C2)=C1)C)N1CCOCC1 OTQWCDNEJVKXKG-RDTXWAMCSA-N 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 3
- UZBQIPPOMKBLAS-UHFFFAOYSA-N diethylazanide Chemical compound CC[N-]CC UZBQIPPOMKBLAS-UHFFFAOYSA-N 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 238000002955 isolation Methods 0.000 description 3
- 150000002688 maleic acid derivatives Chemical class 0.000 description 3
- KWGRBVOPPLSCSI-WPRPVWTQSA-N (-)-ephedrine Chemical compound CN[C@@H](C)[C@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-WPRPVWTQSA-N 0.000 description 2
- OCQAXYHNMWVLRH-QZTJIDSGSA-N (2r,3r)-2,3-dibenzoyl-2,3-dihydroxybutanedioic acid Chemical class O=C([C@@](O)(C(=O)O)[C@](O)(C(O)=O)C(=O)C=1C=CC=CC=1)C1=CC=CC=C1 OCQAXYHNMWVLRH-QZTJIDSGSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical class [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 229910052788 barium Inorganic materials 0.000 description 2
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical class [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 229960002179 ephedrine Drugs 0.000 description 2
- 229960003133 ergot alkaloid Drugs 0.000 description 2
- MDKXBBPLEGPIRI-UHFFFAOYSA-N ethoxyethane;methanol Chemical compound OC.CCOCC MDKXBBPLEGPIRI-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 229910052752 metalloid Inorganic materials 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- YONLFQNRGZXBBF-ZIAGYGMSSA-N (2r,3r)-2,3-dibenzoyloxybutanedioic acid Chemical compound O([C@@H](C(=O)O)[C@@H](OC(=O)C=1C=CC=CC=1)C(O)=O)C(=O)C1=CC=CC=C1 YONLFQNRGZXBBF-ZIAGYGMSSA-N 0.000 description 1
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
- QHKGDMNPQAZMKD-YFKPBYRVSA-N (2s)-2-amino-2-methylbutan-1-ol Chemical compound CC[C@](C)(N)CO QHKGDMNPQAZMKD-YFKPBYRVSA-N 0.000 description 1
- BLTYTOQJAZFMIE-FOIQADDNSA-N (6aR,9R)-7-methyl-N-phenyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide Chemical compound C(=O)([C@H]1CN(C)[C@@H]2CC3=CNC4=CC=CC(C2=C1)=C34)NC1=CC=CC=C1 BLTYTOQJAZFMIE-FOIQADDNSA-N 0.000 description 1
- GENAHGKEFJLNJB-IINYFYTJSA-N (6ar,9s)-7-methyl-6,6a,8,9-tetrahydro-4h-indolo[4,3-fg]quinoline-9-carboxamide Chemical compound C1=CC(C2=C[C@@H](CN([C@@H]2C2)C)C(N)=O)=C3C2=CNC3=C1 GENAHGKEFJLNJB-IINYFYTJSA-N 0.000 description 1
- BKMMTJMQCTUHRP-VKHMYHEASA-N (S)-2-aminopropan-1-ol Chemical compound C[C@H](N)CO BKMMTJMQCTUHRP-VKHMYHEASA-N 0.000 description 1
- BKMMTJMQCTUHRP-UHFFFAOYSA-O 1-hydroxypropan-2-ylazanium Chemical compound CC([NH3+])CO BKMMTJMQCTUHRP-UHFFFAOYSA-O 0.000 description 1
- PJXWCRXOPLGFLX-UHFFFAOYSA-N 2-(benzylamino)propan-1-ol Chemical compound OCC(C)NCC1=CC=CC=C1 PJXWCRXOPLGFLX-UHFFFAOYSA-N 0.000 description 1
- BKMMTJMQCTUHRP-UHFFFAOYSA-N 2-aminopropan-1-ol Chemical compound CC(N)CO BKMMTJMQCTUHRP-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical class [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 101100184147 Caenorhabditis elegans mix-1 gene Proteins 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical class [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 206010056740 Genital discharge Diseases 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- VAYOSLLFUXYJDT-RDTXWAMCSA-N Lysergic acid diethylamide Chemical compound C1=CC(C=2[C@H](N(C)C[C@@H](C=2)C(=O)N(CC)CC)C2)=C3C2=CNC3=C1 VAYOSLLFUXYJDT-RDTXWAMCSA-N 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- QNVPHORBKTTYEV-BWTUWSSMSA-M [O-]C(=O)[C@H]1CN(C)[C@@H]2CC3=CNC4=CC=CC(C2=C1)=C34.[K+] Chemical compound [O-]C(=O)[C@H]1CN(C)[C@@H]2CC3=CNC4=CC=CC(C2=C1)=C34.[K+] QNVPHORBKTTYEV-BWTUWSSMSA-M 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 239000003513 alkali 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
- 239000004411 aluminium Substances 0.000 description 1
- 238000010640 amide synthesis reaction Methods 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000003931 anilides Chemical class 0.000 description 1
- 239000006286 aqueous extract Substances 0.000 description 1
- 239000003637 basic solution Substances 0.000 description 1
- 239000011575 calcium Chemical class 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 239000008139 complexing agent Substances 0.000 description 1
- KWGRBVOPPLSCSI-UHFFFAOYSA-N d-ephedrine Natural products CNC(C)C(O)C1=CC=CC=C1 KWGRBVOPPLSCSI-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- ZZTSQZQUWBFTAT-UHFFFAOYSA-N diethylcyanamide Chemical compound CCN(CC)C#N ZZTSQZQUWBFTAT-UHFFFAOYSA-N 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- YREISLCRUMOYAY-IIPCNOPRSA-N ergometrine maleate Chemical compound OC(=O)\C=C/C(O)=O.C1=CC(C=2[C@H](N(C)C[C@@H](C=2)C(=O)N[C@H](CO)C)C2)=C3C2=CNC3=C1 YREISLCRUMOYAY-IIPCNOPRSA-N 0.000 description 1
- 229940030804 ergonovine maleate Drugs 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- PQVSTLUFSYVLTO-UHFFFAOYSA-N ethyl n-ethoxycarbonylcarbamate Chemical compound CCOC(=O)NC(=O)OCC PQVSTLUFSYVLTO-UHFFFAOYSA-N 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- ZHNUHDYFZUAESO-UHFFFAOYSA-N formamide Substances NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 231100001261 hazardous Toxicity 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- GLXDVVHUTZTUQK-UHFFFAOYSA-M lithium hydroxide monohydrate Substances [Li+].O.[OH-] GLXDVVHUTZTUQK-UHFFFAOYSA-M 0.000 description 1
- 229940040692 lithium hydroxide monohydrate Drugs 0.000 description 1
- 229950002454 lysergide Drugs 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000002738 metalloids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- ZKWFSTHEYLJLEL-UHFFFAOYSA-N morpholine-4-carboxamide Chemical compound NC(=O)N1CCOCC1 ZKWFSTHEYLJLEL-UHFFFAOYSA-N 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 229960001367 tartaric acid Drugs 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical class CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F21—LIGHTING
- F21V—FUNCTIONAL FEATURES OR DETAILS OF LIGHTING DEVICES OR SYSTEMS THEREOF; STRUCTURAL COMBINATIONS OF LIGHTING DEVICES WITH OTHER ARTICLES, NOT OTHERWISE PROVIDED FOR
- F21V7/00—Reflectors for light sources
- F21V7/0008—Reflectors for light sources providing for indirect lighting
-
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F21—LIGHTING
- F21V—FUNCTIONAL FEATURES OR DETAILS OF LIGHTING DEVICES OR SYSTEMS THEREOF; STRUCTURAL COMBINATIONS OF LIGHTING DEVICES WITH OTHER ARTICLES, NOT OTHERWISE PROVIDED FOR
- F21V7/00—Reflectors for light sources
- F21V7/04—Optical design
- F21V7/09—Optical design with a combination of different curvatures
Landscapes
- Engineering & Computer Science (AREA)
- General Engineering & Computer Science (AREA)
- Non-Portable Lighting Devices Or Systems Thereof (AREA)
- Optical Elements Other Than Lenses (AREA)
- Vessels And Coating Films For Discharge Lamps (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE5396/68A SE308699B (zh) | 1968-04-23 | 1968-04-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO121457B true NO121457B (zh) | 1971-03-01 |
Family
ID=20266382
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO1649/69A NO121457B (zh) | 1968-04-23 | 1969-04-22 |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US3609340A (zh) |
| AT (1) | AT285739B (zh) |
| BE (1) | BE731783A (zh) |
| CH (1) | CH501867A (zh) |
| DK (1) | DK123732B (zh) |
| FI (1) | FI49876C (zh) |
| FR (1) | FR2006766A1 (zh) |
| GB (1) | GB1234895A (zh) |
| NL (1) | NL6906298A (zh) |
| NO (1) | NO121457B (zh) |
| SE (1) | SE308699B (zh) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1518930A (en) * | 1974-10-17 | 1978-07-26 | Lucas Electrical Ltd | Lamp assembly |
| US3983039A (en) * | 1975-03-03 | 1976-09-28 | Fusion Systems Corporation | Non-symmetrical reflector for ultraviolet curing |
| FR2368807A2 (fr) * | 1976-10-21 | 1978-05-19 | Lampes Sa | Perfectionnement apporte a un dispositif reflecteur pour la concentration d'un flux d'ondes |
| US4112483A (en) * | 1976-07-28 | 1978-09-05 | Optical Coating Laboratory, Inc. | Lighting fixture and method using multiple reflections |
| DE2740487C3 (de) * | 1977-09-08 | 1981-06-19 | Patent-Treuhand-Gesellschaft für elektrische Glühlampen mbH, 8000 München | Elektronisches Blitzgerät |
| US4310876A (en) * | 1978-06-30 | 1982-01-12 | Small Jr Edward A | Lighting fixture and method using multiple reflections |
| DE2830321C3 (de) * | 1978-07-10 | 1983-02-10 | Patent-Treuhand-Gesellschaft für elektrische Glühlampen mbH, 8000 München | Elektronisches Blitzgerät |
| FR2431090A1 (fr) * | 1978-07-10 | 1980-02-08 | Patent Treuhand Ges Fuer Elektrische Gluehlampen Mbh | Appareil electronique a eclats comportant un reflecteur a elements orientables |
| JPH0670682B2 (ja) * | 1983-08-19 | 1994-09-07 | 日照技研株式会社 | 照明装置 |
| US4583528A (en) * | 1984-11-08 | 1986-04-22 | Jack Bauman | Examining device with improved optical coupling between the light source and light conductor |
| US4669449A (en) * | 1986-02-18 | 1987-06-02 | Jack Bauman | Submergible laryngoscope metallic housing for fiber optics power source |
| US4679547A (en) * | 1986-02-19 | 1987-07-14 | Jack Bauman | Fluid submersible laryngoscope |
| US4694822A (en) * | 1986-04-01 | 1987-09-22 | Jack Bauman | Submergible laryngoscope battery housing |
| US4709312C1 (en) * | 1986-06-24 | 2001-12-11 | Ruud Lighting Inc | Floodlight with improved reflector system |
| US5199782A (en) * | 1991-05-23 | 1993-04-06 | Glen Co. Breda & Associates, Inc. | Illumination system for vanity or the like |
| US5501651A (en) * | 1994-06-13 | 1996-03-26 | Bauman; Jack | Fluid submersible laryngoscope preventing electrolytic current flow |
| SE506827C2 (sv) * | 1996-06-14 | 1998-02-16 | Electrolux Ab | Belysningsanordning vid ett kyl- eller frysskåp |
| JP3256937B2 (ja) * | 1999-03-25 | 2002-02-18 | スタンレー電気株式会社 | 縦型ヘッドランプ |
| JP2001202805A (ja) | 2000-01-14 | 2001-07-27 | Stanley Electric Co Ltd | 灯 具 |
| JP5381348B2 (ja) * | 2009-06-02 | 2014-01-08 | セイコーエプソン株式会社 | 光源装置、照明系、プロジェクター |
| DE102009040753A1 (de) * | 2009-09-10 | 2011-03-24 | MÜNZ, Christoph | Reflektoranordnung |
-
1968
- 1968-04-23 SE SE5396/68A patent/SE308699B/xx unknown
-
1969
- 1969-04-15 CH CH573669A patent/CH501867A/de not_active IP Right Cessation
- 1969-04-16 GB GB09323/69A patent/GB1234895A/en not_active Expired
- 1969-04-17 US US816963A patent/US3609340A/en not_active Expired - Lifetime
- 1969-04-21 BE BE731783D patent/BE731783A/xx unknown
- 1969-04-21 FI FI691159A patent/FI49876C/fi active
- 1969-04-22 NO NO1649/69A patent/NO121457B/no unknown
- 1969-04-22 AT AT389569A patent/AT285739B/de not_active IP Right Cessation
- 1969-04-22 FR FR6912665A patent/FR2006766A1/fr not_active Withdrawn
- 1969-04-22 DK DK220069AA patent/DK123732B/da not_active IP Right Cessation
- 1969-04-23 NL NL6906298A patent/NL6906298A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE1919199B2 (de) | 1976-01-15 |
| DE1919199A1 (de) | 1969-11-06 |
| FI49876C (fi) | 1975-10-10 |
| FR2006766A1 (zh) | 1970-01-02 |
| SE308699B (zh) | 1969-02-24 |
| GB1234895A (en) | 1971-06-09 |
| DK123732B (da) | 1972-07-24 |
| FI49876B (zh) | 1975-06-30 |
| CH501867A (de) | 1971-01-15 |
| NL6906298A (zh) | 1969-10-27 |
| BE731783A (zh) | 1969-10-01 |
| AT285739B (de) | 1970-11-10 |
| US3609340A (en) | 1971-09-28 |
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