NO133209B - - Google Patents
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- Publication number
- NO133209B NO133209B NO168085A NO16808567A NO133209B NO 133209 B NO133209 B NO 133209B NO 168085 A NO168085 A NO 168085A NO 16808567 A NO16808567 A NO 16808567A NO 133209 B NO133209 B NO 133209B
- Authority
- NO
- Norway
- Prior art keywords
- acid
- formula
- lactone
- solution
- methyl
- Prior art date
Links
- 239000002253 acid Substances 0.000 claims description 48
- 150000002596 lactones Chemical class 0.000 claims description 35
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 24
- -1 acetyl- Chemical group 0.000 claims description 23
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 16
- 150000001875 compounds Chemical class 0.000 claims description 15
- 150000003951 lactams Chemical class 0.000 claims description 15
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 14
- 235000011114 ammonium hydroxide Nutrition 0.000 claims description 14
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 10
- APJYDQYYACXCRM-UHFFFAOYSA-N tryptamine Chemical class C1=CC=C2C(CCN)=CNC2=C1 APJYDQYYACXCRM-UHFFFAOYSA-N 0.000 claims description 8
- MTPIGWYBUMYQDT-UHFFFAOYSA-N Deserpidic acid Natural products COC1C(O)CC2CN3CCc4c([nH]c5ccccc45)C3CC2C1C(=O)O MTPIGWYBUMYQDT-UHFFFAOYSA-N 0.000 claims description 6
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 6
- 229910000489 osmium tetroxide Inorganic materials 0.000 claims description 6
- 239000012285 osmium tetroxide Substances 0.000 claims description 6
- JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 claims description 6
- 238000006140 methanolysis reaction Methods 0.000 claims description 5
- MOIPGXQKZSZOQX-UHFFFAOYSA-N carbonyl bromide Chemical compound BrC(Br)=O MOIPGXQKZSZOQX-UHFFFAOYSA-N 0.000 claims description 4
- 230000003287 optical effect Effects 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 239000002262 Schiff base Substances 0.000 claims description 3
- 150000004753 Schiff bases Chemical class 0.000 claims description 3
- 125000002619 bicyclic group Chemical group 0.000 claims description 3
- 230000003197 catalytic effect Effects 0.000 claims description 3
- 230000032050 esterification Effects 0.000 claims description 3
- 238000005886 esterification reaction Methods 0.000 claims description 3
- 150000004702 methyl esters Chemical class 0.000 claims description 3
- KHIWWQKSHDUIBK-UHFFFAOYSA-N periodic acid Chemical compound OI(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-N 0.000 claims description 3
- WRTSLJDGVNEIGP-UHFFFAOYSA-N 2-ethoxycarbonyl-4-hydroxy-3,5-dimethoxybenzoic acid Chemical compound CCOC(=O)C1=C(C(O)=O)C=C(OC)C(O)=C1OC WRTSLJDGVNEIGP-UHFFFAOYSA-N 0.000 claims description 2
- 150000001299 aldehydes Chemical class 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 150000005690 diesters Chemical class 0.000 claims description 2
- 150000004715 keto acids Chemical class 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 159
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 81
- 239000000243 solution Substances 0.000 description 69
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 46
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 24
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 24
- 238000001704 evaporation Methods 0.000 description 24
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 23
- 230000008020 evaporation Effects 0.000 description 21
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 20
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 19
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 19
- 238000010992 reflux Methods 0.000 description 19
- 229910052938 sodium sulfate Inorganic materials 0.000 description 18
- 235000011152 sodium sulphate Nutrition 0.000 description 18
- 239000000203 mixture Substances 0.000 description 17
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 16
- 238000001035 drying Methods 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 11
- 238000001816 cooling Methods 0.000 description 11
- 229960003147 reserpine Drugs 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- QMGVPVSNSZLJIA-FVWCLLPLSA-N strychnine Chemical compound O([C@H]1CC(N([C@H]2[C@H]1[C@H]1C3)C=4C5=CC=CC=4)=O)CC=C1CN1[C@@H]3[C@]25CC1 QMGVPVSNSZLJIA-FVWCLLPLSA-N 0.000 description 11
- 229910021529 ammonia Inorganic materials 0.000 description 10
- 239000000284 extract Substances 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 229960000583 acetic acid Drugs 0.000 description 9
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 8
- 239000012279 sodium borohydride Substances 0.000 description 8
- 229910000033 sodium borohydride Inorganic materials 0.000 description 8
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 7
- 229960001993 deserpidine Drugs 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 239000012362 glacial acetic acid Substances 0.000 description 7
- 239000011734 sodium Substances 0.000 description 7
- 229910052708 sodium Inorganic materials 0.000 description 7
- DNXIKVLOVZVMQF-UHFFFAOYSA-N (3beta,16beta,17alpha,18beta,20alpha)-17-hydroxy-11-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-yohimban-16-carboxylic acid, methyl ester Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(C(=O)OC)C(O)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 DNXIKVLOVZVMQF-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- LCQMZZCPPSWADO-UHFFFAOYSA-N Reserpilin Natural products COC(=O)C1COCC2CN3CCc4c([nH]c5cc(OC)c(OC)cc45)C3CC12 LCQMZZCPPSWADO-UHFFFAOYSA-N 0.000 description 6
- QEVHRUUCFGRFIF-SFWBKIHZSA-N Reserpine Natural products O=C(OC)[C@@H]1[C@H](OC)[C@H](OC(=O)c2cc(OC)c(OC)c(OC)c2)C[C@H]2[C@@H]1C[C@H]1N(C2)CCc2c3c([nH]c12)cc(OC)cc3 QEVHRUUCFGRFIF-SFWBKIHZSA-N 0.000 description 6
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 6
- 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 6
- 235000011121 sodium hydroxide Nutrition 0.000 description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 5
- 229930013930 alkaloid Natural products 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- QEVHRUUCFGRFIF-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C(C5=CC=C(OC)C=C5N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 QEVHRUUCFGRFIF-MDEJGZGSSA-N 0.000 description 5
- CVBMAZKKCSYWQR-BPJCFPRXSA-N Deserpidine Natural products O=C(OC)[C@@H]1[C@H](OC)[C@H](OC(=O)c2cc(OC)c(OC)c(OC)c2)C[C@H]2[C@@H]1C[C@H]1N(C2)CCc2c3c([nH]c12)cccc3 CVBMAZKKCSYWQR-BPJCFPRXSA-N 0.000 description 4
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 4
- QMGVPVSNSZLJIA-UHFFFAOYSA-N Nux Vomica Natural products C1C2C3C4N(C=5C6=CC=CC=5)C(=O)CC3OCC=C2CN2C1C46CC2 QMGVPVSNSZLJIA-UHFFFAOYSA-N 0.000 description 4
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 4
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 239000012299 nitrogen atmosphere Substances 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- SZLZWPPUNLXJEA-UHFFFAOYSA-N 11,17-dimethoxy-18-[3-(3,4,5-trimethoxy-phenyl)-acryloyloxy]-yohimbane-16-carboxylic acid methyl ester Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(C(=O)OC)C(OC)C1OC(=O)C=CC1=CC(OC)=C(OC)C(OC)=C1 SZLZWPPUNLXJEA-UHFFFAOYSA-N 0.000 description 3
- GAZNVVBKELWTBC-UHFFFAOYSA-N 2,3,4-trimethoxybenzoyl chloride Chemical compound COC1=CC=C(C(Cl)=O)C(OC)=C1OC GAZNVVBKELWTBC-UHFFFAOYSA-N 0.000 description 3
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- SZLZWPPUNLXJEA-FMCDHCOASA-N Rescinnamine Natural products O=C(O[C@H]1[C@@H](OC)[C@@H](C(=O)OC)[C@@H]2[C@H](C1)CN1[C@@H](c3[nH]c4c(c3CC1)ccc(OC)c4)C2)/C=C/c1cc(OC)c(OC)c(OC)c1 SZLZWPPUNLXJEA-FMCDHCOASA-N 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- 241001279009 Strychnos toxifera Species 0.000 description 3
- 229940040526 anhydrous sodium acetate Drugs 0.000 description 3
- 239000006286 aqueous extract Substances 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- QFFVPLLCYGOFPU-UHFFFAOYSA-N barium chromate Chemical compound [Ba+2].[O-][Cr]([O-])(=O)=O QFFVPLLCYGOFPU-UHFFFAOYSA-N 0.000 description 3
- 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 3
- CVBMAZKKCSYWQR-WCGOZPBSSA-N deserpidine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C(C5=CC=CC=C5N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 CVBMAZKKCSYWQR-WCGOZPBSSA-N 0.000 description 3
- 238000009826 distribution Methods 0.000 description 3
- 230000007717 exclusion Effects 0.000 description 3
- 239000012452 mother liquor Substances 0.000 description 3
- SZLZWPPUNLXJEA-QEGASFHISA-N rescinnamine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C(C5=CC=C(OC)C=C5N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)\C=C\C1=CC(OC)=C(OC)C(OC)=C1 SZLZWPPUNLXJEA-QEGASFHISA-N 0.000 description 3
- 229960001965 rescinnamine Drugs 0.000 description 3
- 229960005453 strychnine Drugs 0.000 description 3
- 229940095064 tartrate Drugs 0.000 description 3
- AAFCKKQTWKKGJW-UHFFFAOYSA-N 2-(3-methylindol-3-yl)ethanamine Chemical compound CC1(CCN)C=NC2=CC=CC=C12 AAFCKKQTWKKGJW-UHFFFAOYSA-N 0.000 description 2
- QJRWYBIKLXNYLF-UHFFFAOYSA-N 6-methoxy-1h-indole Chemical compound COC1=CC=C2C=CNC2=C1 QJRWYBIKLXNYLF-UHFFFAOYSA-N 0.000 description 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 description 2
- 241000208332 Rauvolfia Species 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 2
- 229950010765 pivalate Drugs 0.000 description 2
- 229940080360 rauwolfia alkaloid Drugs 0.000 description 2
- 238000006722 reduction reaction Methods 0.000 description 2
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- LXHGIGAROAJZRR-UHFFFAOYSA-N (3-ethoxyphenyl)hydrazine Chemical compound CCOC1=CC=CC(NN)=C1 LXHGIGAROAJZRR-UHFFFAOYSA-N 0.000 description 1
- KPIOFCJOKUHZPF-UHFFFAOYSA-N (3-methoxyphenyl)hydrazine Chemical compound COC1=CC=CC(NN)=C1 KPIOFCJOKUHZPF-UHFFFAOYSA-N 0.000 description 1
- DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical compound C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 description 1
- MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical class C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 description 1
- CJDRUOGAGYHKKD-RQBLFBSQSA-N 1pon08459r Chemical compound CN([C@H]1[C@@]2(C[C@@]3([H])[C@@H]([C@@H](O)N42)CC)[H])C2=CC=CC=C2[C@]11C[C@@]4([H])[C@H]3[C@H]1O CJDRUOGAGYHKKD-RQBLFBSQSA-N 0.000 description 1
- JVSFQJZRHXAUGT-UHFFFAOYSA-N 2,2-dimethylpropanoyl chloride Chemical compound CC(C)(C)C(Cl)=O JVSFQJZRHXAUGT-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
- DPTCPATURPWAEC-UHFFFAOYSA-N 3-bromo-1,1-diethoxybutane Chemical compound CCOC(CC(C)Br)OCC DPTCPATURPWAEC-UHFFFAOYSA-N 0.000 description 1
- 241000208327 Apocynaceae Species 0.000 description 1
- 206010012735 Diarrhoea Diseases 0.000 description 1
- 208000000059 Dyspnea Diseases 0.000 description 1
- 206010013975 Dyspnoeas Diseases 0.000 description 1
- 208000034308 Grand mal convulsion Diseases 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- CJDRUOGAGYHKKD-UHFFFAOYSA-N Iso-ajmalin Natural products CN1C2=CC=CC=C2C2(C(C34)O)C1C1CC3C(CC)C(O)N1C4C2 CJDRUOGAGYHKKD-UHFFFAOYSA-N 0.000 description 1
- 238000006219 Matteson homologation reaction Methods 0.000 description 1
- 206010030113 Oedema Diseases 0.000 description 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
- 208000027089 Parkinsonian disease Diseases 0.000 description 1
- 206010034010 Parkinsonism Diseases 0.000 description 1
- 208000008469 Peptic Ulcer Diseases 0.000 description 1
- 244000061121 Rauvolfia serpentina Species 0.000 description 1
- 241000220317 Rosa Species 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 229960004332 ajmaline Drugs 0.000 description 1
- 150000003797 alkaloid derivatives Chemical class 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 230000002686 anti-diuretic effect Effects 0.000 description 1
- 208000006673 asthma Diseases 0.000 description 1
- 230000004531 blood pressure lowering effect Effects 0.000 description 1
- 230000001914 calming effect Effects 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000012505 colouration Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 229960001270 d- tartaric acid Drugs 0.000 description 1
- WLXALCKAKGDNAT-UHFFFAOYSA-N diazoethane Chemical compound CC=[N+]=[N-] WLXALCKAKGDNAT-UHFFFAOYSA-N 0.000 description 1
- LBVWYGNGGJURHQ-UHFFFAOYSA-N dicarbon Chemical compound [C-]#[C+] LBVWYGNGGJURHQ-UHFFFAOYSA-N 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 208000020016 psychiatric disease Diseases 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 238000006257 total synthesis reaction Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- JUPDIHMJFPDGMY-DEYYWGMASA-N yohimban Chemical group C1=CC=C2C(CCN3C[C@@H]4CCCC[C@H]4C[C@H]33)=C3NC2=C1 JUPDIHMJFPDGMY-DEYYWGMASA-N 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
Classifications
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01S—RADIO DIRECTION-FINDING; RADIO NAVIGATION; DETERMINING DISTANCE OR VELOCITY BY USE OF RADIO WAVES; LOCATING OR PRESENCE-DETECTING BY USE OF THE REFLECTION OR RERADIATION OF RADIO WAVES; ANALOGOUS ARRANGEMENTS USING OTHER WAVES
- G01S13/00—Systems using the reflection or reradiation of radio waves, e.g. radar systems; Analogous systems using reflection or reradiation of waves whose nature or wavelength is irrelevant or unspecified
- G01S13/02—Systems using reflection of radio waves, e.g. primary radar systems; Analogous systems
- G01S13/50—Systems of measurement based on relative movement of target
- G01S13/52—Discriminating between fixed and moving objects or between objects moving at different speeds
- G01S13/522—Discriminating between fixed and moving objects or between objects moving at different speeds using transmissions of interrupted pulse modulated waves
- G01S13/524—Discriminating between fixed and moving objects or between objects moving at different speeds using transmissions of interrupted pulse modulated waves based upon the phase or frequency shift resulting from movement of objects, with reference to the transmitted signals, e.g. coherent MTi
- G01S13/526—Discriminating between fixed and moving objects or between objects moving at different speeds using transmissions of interrupted pulse modulated waves based upon the phase or frequency shift resulting from movement of objects, with reference to the transmitted signals, e.g. coherent MTi performing filtering on the whole spectrum without loss of range information, e.g. using delay line cancellers or comb filters
- G01S13/528—Discriminating between fixed and moving objects or between objects moving at different speeds using transmissions of interrupted pulse modulated waves based upon the phase or frequency shift resulting from movement of objects, with reference to the transmitted signals, e.g. coherent MTi performing filtering on the whole spectrum without loss of range information, e.g. using delay line cancellers or comb filters with elimination of blind speeds
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01S—RADIO DIRECTION-FINDING; RADIO NAVIGATION; DETERMINING DISTANCE OR VELOCITY BY USE OF RADIO WAVES; LOCATING OR PRESENCE-DETECTING BY USE OF THE REFLECTION OR RERADIATION OF RADIO WAVES; ANALOGOUS ARRANGEMENTS USING OTHER WAVES
- G01S13/00—Systems using the reflection or reradiation of radio waves, e.g. radar systems; Analogous systems using reflection or reradiation of waves whose nature or wavelength is irrelevant or unspecified
- G01S13/02—Systems using reflection of radio waves, e.g. primary radar systems; Analogous systems
- G01S13/50—Systems of measurement based on relative movement of target
- G01S13/52—Discriminating between fixed and moving objects or between objects moving at different speeds
- G01S13/522—Discriminating between fixed and moving objects or between objects moving at different speeds using transmissions of interrupted pulse modulated waves
- G01S13/524—Discriminating between fixed and moving objects or between objects moving at different speeds using transmissions of interrupted pulse modulated waves based upon the phase or frequency shift resulting from movement of objects, with reference to the transmitted signals, e.g. coherent MTi
- G01S13/5242—Discriminating between fixed and moving objects or between objects moving at different speeds using transmissions of interrupted pulse modulated waves based upon the phase or frequency shift resulting from movement of objects, with reference to the transmitted signals, e.g. coherent MTi with means for platform motion or scan motion compensation, e.g. airborne MTI
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01S—RADIO DIRECTION-FINDING; RADIO NAVIGATION; DETERMINING DISTANCE OR VELOCITY BY USE OF RADIO WAVES; LOCATING OR PRESENCE-DETECTING BY USE OF THE REFLECTION OR RERADIATION OF RADIO WAVES; ANALOGOUS ARRANGEMENTS USING OTHER WAVES
- G01S13/00—Systems using the reflection or reradiation of radio waves, e.g. radar systems; Analogous systems using reflection or reradiation of waves whose nature or wavelength is irrelevant or unspecified
- G01S13/02—Systems using reflection of radio waves, e.g. primary radar systems; Analogous systems
- G01S13/50—Systems of measurement based on relative movement of target
- G01S13/58—Velocity or trajectory determination systems; Sense-of-movement determination systems
- G01S13/64—Velocity measuring systems using range gates
Landscapes
- Engineering & Computer Science (AREA)
- Radar, Positioning & Navigation (AREA)
- Remote Sensing (AREA)
- Computer Networks & Wireless Communication (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Radar Systems Or Details Thereof (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US552556A US3341847A (en) | 1966-05-24 | 1966-05-24 | Platform motion compensation of a coherent mti system |
Publications (2)
Publication Number | Publication Date |
---|---|
NO133209B true NO133209B (de) | 1975-12-15 |
NO133209C NO133209C (de) | 1976-03-24 |
Family
ID=24205847
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO168085A NO133209C (de) | 1966-05-24 | 1967-05-10 |
Country Status (7)
Country | Link |
---|---|
US (1) | US3341847A (de) |
BE (1) | BE695181A (de) |
DE (1) | DE1591312A1 (de) |
DK (1) | DK129812B (de) |
NL (1) | NL6703153A (de) |
NO (1) | NO133209C (de) |
SE (2) | SE354125B (de) |
Families Citing this family (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3707718A (en) * | 1969-02-18 | 1972-12-26 | Westinghouse Electric Corp | Radar system |
US3611139A (en) * | 1970-02-25 | 1971-10-05 | Us Navy | Orthogonal mixer f{11 {0 f{11 {0 repeater |
US3706989A (en) * | 1970-10-28 | 1972-12-19 | Us Air Force | Digital motion compensation system for radar platforms |
US3755813A (en) * | 1971-11-01 | 1973-08-28 | Hughes Aircraft Co | Moving target signal processor |
JPS4859791A (de) * | 1971-11-24 | 1973-08-22 | ||
US4062011A (en) * | 1972-08-21 | 1977-12-06 | Control Data Corporation | MTI System processor and method |
US3866219A (en) * | 1973-07-05 | 1975-02-11 | Hughes Aircraft Co | Radar system with target illumination by different waveforms |
US3990076A (en) * | 1975-05-22 | 1976-11-02 | United Technologies Corporation | Pseudo pulse doppler radar |
FR2315703A1 (fr) * | 1975-06-24 | 1977-01-21 | Thomson Csf | Systeme radar a vision laterale |
US4642641A (en) * | 1976-07-29 | 1987-02-10 | Westinghouse Electric Corp. | Variable PRF target tracking radar |
US4084158A (en) * | 1977-01-03 | 1978-04-11 | Raytheon Company | Method of operating synthetic aperture radar |
US4217581A (en) * | 1978-09-22 | 1980-08-12 | The United States Of America As Represented By The Secretary Of The Navy | High range resolution radar rate aided range tracker |
US4290066A (en) * | 1979-10-12 | 1981-09-15 | Motorola Inc. | High speed adaptive clutter filter |
FR2501378B1 (fr) * | 1981-03-06 | 1985-07-26 | Dassault Electronique | Procede et dispositif pour ameliorer la visibilite doppler d'un radar |
FR2629923A1 (fr) * | 1982-05-14 | 1989-10-13 | Dassault Electronique | Procede et dispositif notamment pour l'amelioration de la selectivite angulaire d'un radar aeroporte utilise en detection de sol |
US7068215B2 (en) * | 2004-10-08 | 2006-06-27 | Raytheon Company | Reducing antenna boresight error |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE977246C (de) * | 1954-05-18 | 1965-07-29 | Ernst Dr Schulze | Verfahren zur Beschraenkung der Anzeige von Impulsradargeraeten auf bestimmte Flugziele |
US3011166A (en) * | 1956-08-29 | 1961-11-28 | Westinghouse Electric Corp | Pulse doppler radar system |
DE1033281B (de) * | 1957-03-09 | 1958-07-03 | Telefunken Gmbh | Verfahren zur Festzeichenunterdrueckung in einem Impulsrueckstrahlgeraet mit Sichtanzeige |
-
1966
- 1966-05-24 US US552556A patent/US3341847A/en not_active Expired - Lifetime
-
1967
- 1967-02-28 NL NL6703153A patent/NL6703153A/xx unknown
- 1967-03-08 BE BE695181D patent/BE695181A/xx unknown
- 1967-05-10 NO NO168085A patent/NO133209C/no unknown
- 1967-05-22 DE DE19671591312 patent/DE1591312A1/de active Pending
- 1967-05-23 SE SE07203/67A patent/SE354125B/xx unknown
- 1967-05-23 SE SE7209303*3A patent/SE377503B/xx unknown
- 1967-05-23 DK DK269167AA patent/DK129812B/da unknown
Also Published As
Publication number | Publication date |
---|---|
SE354125B (de) | 1973-02-26 |
DK129812B (da) | 1974-11-18 |
NO133209C (de) | 1976-03-24 |
NL6703153A (de) | 1967-11-27 |
DE1591312A1 (de) | 1971-12-30 |
SE377503B (de) | 1975-07-07 |
BE695181A (de) | 1967-08-14 |
US3341847A (en) | 1967-09-12 |
DK129812C (de) | 1975-05-26 |
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