DD251749A5 - Verfahren zur herstellung von 2,4-diphenyl-1,3-dioxian-derivaten - Google Patents

Verfahren zur herstellung von 2,4-diphenyl-1,3-dioxian-derivaten Download PDF

Info

Publication number: DD251749A5
Authority: DD; German Democratic Republic
Prior art keywords: formula; cis; acid; hydrogen; compound
Prior art date: 1985-05-10

Application number

DD86290093A

Other languages

German (de)

English (en)

Inventor

Andrew G Brewster

George R Brown

Michael J Smithers

Original Assignee

��@��@��@��k��

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1985-05-10

Filing date

1986-05-09

Publication date

1987-11-25

1986-05-09 Application filed by ��@��@��@��k�� filed Critical ��@��@��@��k��

1987-11-25 Publication of DD251749A5 publication Critical patent/DD251749A5/de

Links

238000000034 method Methods 0.000 title claims abstract description 40
230000008569 process Effects 0.000 title claims abstract description 13
238000002360 preparation method Methods 0.000 title claims abstract description 7
150000001875 compounds Chemical class 0.000 claims abstract description 71
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 40
239000001257 hydrogen Substances 0.000 claims abstract description 22
150000003839 salts Chemical class 0.000 claims abstract description 20
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 9
229910052731 fluorine Inorganic materials 0.000 claims abstract description 7
150000002431 hydrogen Chemical group 0.000 claims abstract description 7
239000011737 fluorine Substances 0.000 claims abstract description 6
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract description 5
TUJMFENFEJTHDG-UHFFFAOYSA-N 2,4-diphenyl-1,3-dioxane Chemical class O1CCC(C=2C=CC=CC=2)OC1C1=CC=CC=C1 TUJMFENFEJTHDG-UHFFFAOYSA-N 0.000 claims abstract description 4
229910052794 bromium Inorganic materials 0.000 claims abstract 2
229910052801 chlorine Inorganic materials 0.000 claims abstract 2
-1 cyano, methoxy Chemical group 0.000 claims description 13
239000007858 starting material Substances 0.000 claims description 12
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
NIONDZDPPYHYKY-SNAWJCMRSA-N (2E)-hexenoic acid Chemical compound CCC\C=C\C(O)=O NIONDZDPPYHYKY-SNAWJCMRSA-N 0.000 claims description 9
125000000217 alkyl group Chemical group 0.000 claims description 8
125000003118 aryl group Chemical group 0.000 claims description 8
125000004432 carbon atom Chemical group C* 0.000 claims description 8
239000002585 base Substances 0.000 claims description 6
150000001768 cations Chemical class 0.000 claims description 6
238000007796 conventional method Methods 0.000 claims description 6
125000000532 dioxanyl group Chemical group 0.000 claims description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
125000006239 protecting group Chemical group 0.000 claims description 6
229910052705 radium Inorganic materials 0.000 claims description 6
229910052701 rubidium Inorganic materials 0.000 claims description 6
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 5
150000001299 aldehydes Chemical class 0.000 claims description 5
150000003935 benzaldehydes Chemical class 0.000 claims description 5
150000002373 hemiacetals Chemical class 0.000 claims description 5
XMVJITFPVVRMHC-UHFFFAOYSA-N roxarsone Chemical group OC1=CC=C([As](O)(O)=O)C=C1[N+]([O-])=O XMVJITFPVVRMHC-UHFFFAOYSA-N 0.000 claims description 5
125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 claims description 3
229910052783 alkali metal Inorganic materials 0.000 claims description 3
239000003153 chemical reaction reagent Substances 0.000 claims description 3
150000002989 phenols Chemical class 0.000 claims description 3
230000002378 acidificating effect Effects 0.000 claims description 2
150000001340 alkali metals Chemical class 0.000 claims description 2
229910052784 alkaline earth metal Inorganic materials 0.000 claims description 2
229910052782 aluminium Inorganic materials 0.000 claims description 2
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical class [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 2
150000001412 amines Chemical class 0.000 claims description 2
PSZDOEIIIJFCFE-OSQDELBUSA-N erythrodiol Chemical class C1C[C@H](O)C(C)(C)[C@@H]2CC[C@@]3(C)[C@]4(C)CC[C@@]5(CO)CCC(C)(C)C[C@H]5C4=CC[C@@H]3[C@]21C PSZDOEIIIJFCFE-OSQDELBUSA-N 0.000 claims description 2
125000001153 fluoro group Chemical group F* 0.000 claims description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical class [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
150000001342 alkaline earth metals Chemical class 0.000 claims 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
239000003054 catalyst Substances 0.000 claims 1
239000000460 chlorine Chemical group 0.000 claims 1
230000008485 antagonism Effects 0.000 abstract description 7
239000008194 pharmaceutical composition Substances 0.000 abstract description 6
201000010099 disease Diseases 0.000 abstract description 5
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 5
239000003814 drug Substances 0.000 abstract description 3
230000000144 pharmacologic effect Effects 0.000 abstract description 3
DSNBHJFQCNUKMA-SCKDECHMSA-N thromboxane A2 Chemical compound OC(=O)CCC\C=C/C[C@@H]1[C@@H](/C=C/[C@@H](O)CCCCC)O[C@@H]2O[C@H]1C2 DSNBHJFQCNUKMA-SCKDECHMSA-N 0.000 abstract description 3
NIONDZDPPYHYKY-UHFFFAOYSA-N 2-hexenoic acid Chemical class CCCC=CC(O)=O NIONDZDPPYHYKY-UHFFFAOYSA-N 0.000 abstract description 2
GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 abstract 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 193
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 93
239000000203 mixture Substances 0.000 description 73
235000019439 ethyl acetate Nutrition 0.000 description 66
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 57
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 55
239000000243 solution Substances 0.000 description 55
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 44
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 44
239000003921 oil Substances 0.000 description 38
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
238000005481 NMR spectroscopy Methods 0.000 description 33
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 32
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 29
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 26
238000012360 testing method Methods 0.000 description 26
239000007787 solid Substances 0.000 description 25
239000000284 extract Substances 0.000 description 23
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 23
239000002253 acid Substances 0.000 description 22
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 22
238000003818 flash chromatography Methods 0.000 description 21
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 17
239000002904 solvent Substances 0.000 description 16
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 16
229910052786 argon Inorganic materials 0.000 description 13
238000002844 melting Methods 0.000 description 13
230000008018 melting Effects 0.000 description 13
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
239000012230 colorless oil Substances 0.000 description 12
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 11
238000006243 chemical reaction Methods 0.000 description 11
230000000694 effects Effects 0.000 description 11
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 11
239000000725 suspension Substances 0.000 description 11
DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 10
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 9
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 9
239000008346 aqueous phase Substances 0.000 description 9
238000001816 cooling Methods 0.000 description 9
GUVUOGQBMYCBQP-UHFFFAOYSA-N dmpu Chemical compound CN1CCCN(C)C1=O GUVUOGQBMYCBQP-UHFFFAOYSA-N 0.000 description 9
239000000463 material Substances 0.000 description 9
238000003756 stirring Methods 0.000 description 9
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 8
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 8
239000000377 silicon dioxide Substances 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
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 7
239000000443 aerosol Substances 0.000 description 7
239000005557 antagonist Substances 0.000 description 7
239000003085 diluting agent Substances 0.000 description 7
238000001914 filtration Methods 0.000 description 7
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 7
238000001953 recrystallisation Methods 0.000 description 7
206010006482 Bronchospasm Diseases 0.000 description 6
241001465754 Metazoa Species 0.000 description 6
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 6
230000007885 bronchoconstriction Effects 0.000 description 6
230000005764 inhibitory process Effects 0.000 description 6
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
229910052708 sodium Inorganic materials 0.000 description 6
239000011734 sodium Substances 0.000 description 6
239000012312 sodium hydride Substances 0.000 description 6
229910000104 sodium hydride Inorganic materials 0.000 description 6
239000003826 tablet Substances 0.000 description 6
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 5
239000002775 capsule Substances 0.000 description 5
239000006185 dispersion Substances 0.000 description 5
239000000706 filtrate Substances 0.000 description 5
239000005457 ice water Substances 0.000 description 5
239000008101 lactose Substances 0.000 description 5
239000010410 layer Substances 0.000 description 5
229910052744 lithium Inorganic materials 0.000 description 5
239000002480 mineral oil Substances 0.000 description 5
235000010446 mineral oil Nutrition 0.000 description 5
FPYUJUBAXZAQNL-UHFFFAOYSA-N 2-chlorobenzaldehyde Chemical compound ClC1=CC=CC=C1C=O FPYUJUBAXZAQNL-UHFFFAOYSA-N 0.000 description 4
NKVJKVMGJABKHV-UHFFFAOYSA-N 3-carboxypropyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CCCC(=O)O)C1=CC=CC=C1 NKVJKVMGJABKHV-UHFFFAOYSA-N 0.000 description 4
239000004338 Dichlorodifluoromethane Substances 0.000 description 4
241000283973 Oryctolagus cuniculus Species 0.000 description 4
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
241000700159 Rattus Species 0.000 description 4
239000004147 Sorbitan trioleate Substances 0.000 description 4
PRXRUNOAOLTIEF-ADSICKODSA-N Sorbitan trioleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](OC(=O)CCCCCCC\C=C/CCCCCCCC)[C@H]1OC[C@H](O)[C@H]1OC(=O)CCCCCCC\C=C/CCCCCCCC PRXRUNOAOLTIEF-ADSICKODSA-N 0.000 description 4
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 4
239000012267 brine Substances 0.000 description 4
239000003795 chemical substances by application Substances 0.000 description 4
125000004093 cyano group Chemical group *C#N 0.000 description 4
PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 4
235000019404 dichlorodifluoromethane Nutrition 0.000 description 4
238000009472 formulation Methods 0.000 description 4
238000004128 high performance liquid chromatography Methods 0.000 description 4
238000002347 injection Methods 0.000 description 4
239000007924 injection Substances 0.000 description 4
239000000543 intermediate Substances 0.000 description 4
235000019359 magnesium stearate Nutrition 0.000 description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
238000010992 reflux Methods 0.000 description 4
235000017557 sodium bicarbonate Nutrition 0.000 description 4
229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
235000019337 sorbitan trioleate Nutrition 0.000 description 4
229960000391 sorbitan trioleate Drugs 0.000 description 4
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 4
229940029284 trichlorofluoromethane Drugs 0.000 description 4
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 4
DDMOUSALMHHKOS-UHFFFAOYSA-N 1,2-dichloro-1,1,2,2-tetrafluoroethane Chemical compound FC(F)(Cl)C(F)(F)Cl DDMOUSALMHHKOS-UHFFFAOYSA-N 0.000 description 3
HEWZVZIVELJPQZ-UHFFFAOYSA-N 2,2-dimethoxypropane Chemical compound COC(C)(C)OC HEWZVZIVELJPQZ-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
241000282472 Canis lupus familiaris Species 0.000 description 3
WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 3
229920002261 Corn starch Polymers 0.000 description 3
206010020772 Hypertension Diseases 0.000 description 3
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 3
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
150000001241 acetals Chemical class 0.000 description 3
230000002776 aggregation Effects 0.000 description 3
238000004220 aggregation Methods 0.000 description 3
230000003042 antagnostic effect Effects 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
239000012300 argon atmosphere Substances 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
239000008120 corn starch Substances 0.000 description 3
238000010511 deprotection reaction Methods 0.000 description 3
229940087091 dichlorotetrafluoroethane Drugs 0.000 description 3
231100000673 dose–response relationship Toxicity 0.000 description 3
238000010828 elution Methods 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
238000001990 intravenous administration Methods 0.000 description 3
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 3
230000036961 partial effect Effects 0.000 description 3
229910052700 potassium Inorganic materials 0.000 description 3
239000011591 potassium Substances 0.000 description 3
229960003975 potassium Drugs 0.000 description 3
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical class [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 3
208000010110 spontaneous platelet aggregation Diseases 0.000 description 3
125000001424 substituent group Chemical group 0.000 description 3
238000010998 test method Methods 0.000 description 3
239000008215 water for injection Substances 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
DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 2
LADRVCLLYUDKSH-UHFFFAOYSA-N 2-(5-fluoro-2-methoxyphenyl)-5-oxooxolane-3-carboxylic acid Chemical compound COC1=CC=C(F)C=C1C1C(C(O)=O)CC(=O)O1 LADRVCLLYUDKSH-UHFFFAOYSA-N 0.000 description 2
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
PKZJLOCLABXVMC-UHFFFAOYSA-N 2-Methoxybenzaldehyde Chemical compound COC1=CC=CC=C1C=O PKZJLOCLABXVMC-UHFFFAOYSA-N 0.000 description 2
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
229920000623 Cellulose acetate phthalate Polymers 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
239000005977 Ethylene Substances 0.000 description 2
208000019693 Lung disease Diseases 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 2
XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
239000003377 acid catalyst Substances 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
230000009471 action Effects 0.000 description 2
125000002252 acyl group Chemical group 0.000 description 2
238000006136 alcoholysis reaction Methods 0.000 description 2
239000006286 aqueous extract Substances 0.000 description 2
YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 description 2
GONOPSZTUGRENK-UHFFFAOYSA-N benzyl(trichloro)silane Chemical compound Cl[Si](Cl)(Cl)CC1=CC=CC=C1 GONOPSZTUGRENK-UHFFFAOYSA-N 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 2
210000004369 blood Anatomy 0.000 description 2
239000008280 blood Substances 0.000 description 2
125000001246 bromo group Chemical group Br* 0.000 description 2
229940081734 cellulose acetate phthalate Drugs 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
239000012141 concentrate Substances 0.000 description 2
239000013078 crystal Substances 0.000 description 2
230000001186 cumulative effect Effects 0.000 description 2
KWGRBVOPPLSCSI-UHFFFAOYSA-N d-ephedrine Natural products CNC(C)C(O)C1=CC=CC=C1 KWGRBVOPPLSCSI-UHFFFAOYSA-N 0.000 description 2
238000004821 distillation Methods 0.000 description 2
239000002552 dosage form Substances 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
125000004356 hydroxy functional group Chemical group O* 0.000 description 2
229910052500 inorganic mineral Inorganic materials 0.000 description 2
239000002198 insoluble material Substances 0.000 description 2
210000004731 jugular vein Anatomy 0.000 description 2
ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 2
235000010755 mineral Nutrition 0.000 description 2
239000011707 mineral Substances 0.000 description 2
FUZZWVXGSFPDMH-UHFFFAOYSA-N n-hexanoic acid Natural products CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 2
230000003287 optical effect Effects 0.000 description 2
239000012044 organic layer Substances 0.000 description 2
235000006408 oxalic acid Nutrition 0.000 description 2
229940068918 polyethylene glycol 400 Drugs 0.000 description 2
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
238000000746 purification Methods 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
239000012047 saturated solution Substances 0.000 description 2
PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 2
239000001488 sodium phosphate Substances 0.000 description 2
229910000162 sodium phosphate Inorganic materials 0.000 description 2
QJDUDPQVDAASMV-UHFFFAOYSA-M sodium;ethanethiolate Chemical compound [Na+].CC[S-] QJDUDPQVDAASMV-UHFFFAOYSA-M 0.000 description 2
239000011343 solid material Substances 0.000 description 2
239000000375 suspending agent Substances 0.000 description 2
FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 2
125000004187 tetrahydropyran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 2
WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 2
CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 2
229940124597 therapeutic agent Drugs 0.000 description 2
230000001225 therapeutic effect Effects 0.000 description 2
238000002560 therapeutic procedure Methods 0.000 description 2
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 2
230000002792 vascular Effects 0.000 description 2
239000011592 zinc chloride Substances 0.000 description 2
235000005074 zinc chloride Nutrition 0.000 description 2
KWGRBVOPPLSCSI-PSASIEDQSA-N (1s,2r)-2-(methylamino)-1-phenylpropan-1-ol Chemical compound CN[C@H](C)[C@@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-PSASIEDQSA-N 0.000 description 1
CUNWUEBNSZSNRX-RKGWDQTMSA-N (2r,3r,4r,5s)-hexane-1,2,3,4,5,6-hexol;(z)-octadec-9-enoic acid Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.CCCCCCCC\C=C/CCCCCCCC(O)=O.CCCCCCCC\C=C/CCCCCCCC(O)=O.CCCCCCCC\C=C/CCCCCCCC(O)=O CUNWUEBNSZSNRX-RKGWDQTMSA-N 0.000 description 1
WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
ZORQXIQZAOLNGE-UHFFFAOYSA-N 1,1-difluorocyclohexane Chemical compound FC1(F)CCCCC1 ZORQXIQZAOLNGE-UHFFFAOYSA-N 0.000 description 1
NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
150000000093 1,3-dioxanes Chemical class 0.000 description 1
YZUPZGFPHUVJKC-UHFFFAOYSA-N 1-bromo-2-methoxyethane Chemical compound COCCBr YZUPZGFPHUVJKC-UHFFFAOYSA-N 0.000 description 1
JLPULHDHAOZNQI-ZTIMHPMXSA-N 1-hexadecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C/C\C=C/CCCCC JLPULHDHAOZNQI-ZTIMHPMXSA-N 0.000 description 1
PZNPLUBHRSSFHT-RRHRGVEJSA-N 1-hexadecanoyl-2-octadecanoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCCCC(=O)O[C@@H](COP([O-])(=O)OCC[N+](C)(C)C)COC(=O)CCCCCCCCCCCCCCC PZNPLUBHRSSFHT-RRHRGVEJSA-N 0.000 description 1
RQEUFEKYXDPUSK-UHFFFAOYSA-N 1-phenylethylamine Chemical compound CC(N)C1=CC=CC=C1 RQEUFEKYXDPUSK-UHFFFAOYSA-N 0.000 description 1
RPLSBADGISFNSI-UHFFFAOYSA-N 2,2-dimethyl-1,3-dioxane Chemical class CC1(C)OCCCO1 RPLSBADGISFNSI-UHFFFAOYSA-N 0.000 description 1
LMMNYYZCVYAOOF-UHFFFAOYSA-N 2-(2-methoxyphenyl)-5-oxooxolane-3-carboxylic acid Chemical compound COC1=CC=CC=C1C1C(C(O)=O)CC(=O)O1 LMMNYYZCVYAOOF-UHFFFAOYSA-N 0.000 description 1
FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 1
QVTPWONEVZJCCS-UHFFFAOYSA-N 2-formylbenzonitrile Chemical compound O=CC1=CC=CC=C1C#N QVTPWONEVZJCCS-UHFFFAOYSA-N 0.000 description 1
YURNCBVQZBJDAJ-UHFFFAOYSA-N 2-heptenoic acid Chemical compound CCCCC=CC(O)=O YURNCBVQZBJDAJ-UHFFFAOYSA-N 0.000 description 1
LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
GFHCXVJXSLGRJR-UHFFFAOYSA-N 3-fluoro-2-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=CC(F)=C1O GFHCXVJXSLGRJR-UHFFFAOYSA-N 0.000 description 1
MEOOXZGGYVXUSG-UHFFFAOYSA-N 3-fluoro-2-methoxybenzoic acid Chemical compound COC1=C(F)C=CC=C1C(O)=O MEOOXZGGYVXUSG-UHFFFAOYSA-N 0.000 description 1
WJLYPIGIRQBXFF-UHFFFAOYSA-N 3-fluoro-2-methoxybenzoyl chloride Chemical compound COC1=C(F)C=CC=C1C(Cl)=O WJLYPIGIRQBXFF-UHFFFAOYSA-N 0.000 description 1
125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 description 1
JLNTXIRAZPRKMD-UHFFFAOYSA-N 4-[bromo(triphenyl)-$l^{5}-phosphanyl]butanoic acid Chemical compound C=1C=CC=CC=1P(Br)(C=1C=CC=CC=1)(CCCC(=O)O)C1=CC=CC=C1 JLNTXIRAZPRKMD-UHFFFAOYSA-N 0.000 description 1
125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 description 1
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
XTWYTFMLZFPYCI-KQYNXXCUSA-N 5'-adenylphosphoric acid Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O XTWYTFMLZFPYCI-KQYNXXCUSA-N 0.000 description 1
CRLDWFVRQNUUSZ-UHFFFAOYSA-N 5-fluoro-2-methoxybenzaldehyde Chemical compound COC1=CC=C(F)C=C1C=O CRLDWFVRQNUUSZ-UHFFFAOYSA-N 0.000 description 1
RVDLHGSZWAELAU-UHFFFAOYSA-N 5-tert-butylthiophene-2-carbonyl chloride Chemical compound CC(C)(C)C1=CC=C(C(Cl)=O)S1 RVDLHGSZWAELAU-UHFFFAOYSA-N 0.000 description 1
QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
206010000060 Abdominal distension Diseases 0.000 description 1
XTWYTFMLZFPYCI-UHFFFAOYSA-N Adenosine diphosphate Natural products C1=NC=2C(N)=NC=NC=2N1C1OC(COP(O)(=O)OP(O)(O)=O)C(O)C1O XTWYTFMLZFPYCI-UHFFFAOYSA-N 0.000 description 1
206010002383 Angina Pectoris Diseases 0.000 description 1
201000001320 Atherosclerosis Diseases 0.000 description 1
208000012639 Balance disease Diseases 0.000 description 1
KUVIULQEHSCUHY-XYWKZLDCSA-N Beclometasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(Cl)[C@@H]1[C@@H]1C[C@H](C)[C@@](C(=O)COC(=O)CC)(OC(=O)CC)[C@@]1(C)C[C@@H]2O KUVIULQEHSCUHY-XYWKZLDCSA-N 0.000 description 1
COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
241000700199 Cavia porcellus Species 0.000 description 1
241000282693 Cercopithecidae Species 0.000 description 1
229940126062 Compound A Drugs 0.000 description 1
101000783577 Dendroaspis angusticeps Thrombostatin Proteins 0.000 description 1
101000783578 Dendroaspis jamesoni kaimosae Dendroaspin Proteins 0.000 description 1
208000000059 Dyspnea Diseases 0.000 description 1
206010013975 Dyspnoeas Diseases 0.000 description 1
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
241000282326 Felis catus Species 0.000 description 1
NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
239000012448 Lithium borohydride Substances 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
238000003820 Medium-pressure liquid chromatography Methods 0.000 description 1
208000019695 Migraine disease Diseases 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
239000005642 Oleic acid Substances 0.000 description 1
ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
QGMRQYFBGABWDR-UHFFFAOYSA-M Pentobarbital sodium Chemical compound [Na+].CCCC(C)C1(CC)C(=O)NC(=O)[N-]C1=O QGMRQYFBGABWDR-UHFFFAOYSA-M 0.000 description 1
208000018262 Peripheral vascular disease Diseases 0.000 description 1
229940099471 Phosphodiesterase inhibitor Drugs 0.000 description 1
206010035664 Pneumonia Diseases 0.000 description 1
NPYPAHLBTDXSSS-UHFFFAOYSA-N Potassium ion Chemical compound [K+] NPYPAHLBTDXSSS-UHFFFAOYSA-N 0.000 description 1
208000010378 Pulmonary Embolism Diseases 0.000 description 1
GUGOEEXESWIERI-UHFFFAOYSA-N Terfenadine Chemical compound C1=CC(C(C)(C)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 GUGOEEXESWIERI-UHFFFAOYSA-N 0.000 description 1
GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
241000009298 Trigla lyra Species 0.000 description 1
OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 1
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
CSCPPACGZOOCGX-WFGJKAKNSA-N acetone d6 Chemical compound [2H]C([2H])([2H])C(=O)C([2H])([2H])[2H] CSCPPACGZOOCGX-WFGJKAKNSA-N 0.000 description 1
238000005903 acid hydrolysis reaction Methods 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
239000004479 aerosol dispenser Substances 0.000 description 1
125000003342 alkenyl group Chemical group 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
235000019270 ammonium chloride Nutrition 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
238000010171 animal model Methods 0.000 description 1
230000001387 anti-histamine Effects 0.000 description 1
239000000739 antihistaminic agent Substances 0.000 description 1
239000002220 antihypertensive agent Substances 0.000 description 1
229940030600 antihypertensive agent Drugs 0.000 description 1
239000003524 antilipemic agent Substances 0.000 description 1
229940127218 antiplatelet drug Drugs 0.000 description 1
239000003125 aqueous solvent Substances 0.000 description 1
229940114079 arachidonic acid Drugs 0.000 description 1
235000021342 arachidonic acid Nutrition 0.000 description 1
239000003849 aromatic solvent Substances 0.000 description 1
125000003710 aryl alkyl group Chemical group 0.000 description 1
238000003556 assay Methods 0.000 description 1
208000006673 asthma Diseases 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
238000010945 base-catalyzed hydrolysis reactiony Methods 0.000 description 1
229950000210 beclometasone dipropionate Drugs 0.000 description 1
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 description 1
239000002876 beta blocker Substances 0.000 description 1
229940030611 beta-adrenergic blocking agent Drugs 0.000 description 1
239000004305 biphenyl Substances 0.000 description 1
235000010290 biphenyl Nutrition 0.000 description 1
208000024330 bloating Diseases 0.000 description 1
230000023555 blood coagulation Effects 0.000 description 1
230000036772 blood pressure Effects 0.000 description 1
210000004204 blood vessel Anatomy 0.000 description 1
230000037396 body weight Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 1
229910010277 boron hydride Inorganic materials 0.000 description 1
UWTDFICHZKXYAC-UHFFFAOYSA-N boron;oxolane Chemical compound [B].C1CCOC1 UWTDFICHZKXYAC-UHFFFAOYSA-N 0.000 description 1
206010006451 bronchitis Diseases 0.000 description 1
159000000007 calcium salts Chemical class 0.000 description 1
238000004364 calculation method Methods 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 1
210000001715 carotid artery Anatomy 0.000 description 1
239000000969 carrier Substances 0.000 description 1
208000026106 cerebrovascular disease Diseases 0.000 description 1
238000001311 chemical methods and process Methods 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
YYDZNOUMWKJXMG-UHFFFAOYSA-N chloro(phenyl)phosphane Chemical compound ClPC1=CC=CC=C1 YYDZNOUMWKJXMG-UHFFFAOYSA-N 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
239000011248 coating agent Substances 0.000 description 1
238000000576 coating method Methods 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
229960000265 cromoglicic acid Drugs 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
238000010908 decantation Methods 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
230000007547 defect Effects 0.000 description 1
238000011161 development Methods 0.000 description 1
ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 1
230000006806 disease prevention Effects 0.000 description 1
VLARUOGDXDTHEH-UHFFFAOYSA-L disodium cromoglycate Chemical compound [Na+].[Na+].O1C(C([O-])=O)=CC(=O)C2=C1C=CC=C2OCC(O)COC1=CC=CC2=C1C(=O)C=C(C([O-])=O)O2 VLARUOGDXDTHEH-UHFFFAOYSA-L 0.000 description 1
230000009429 distress Effects 0.000 description 1
239000002702 enteric coating Substances 0.000 description 1
238000009505 enteric coating Methods 0.000 description 1
229960002179 ephedrine Drugs 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 description 1
239000012259 ether extract Substances 0.000 description 1
239000002038 ethyl acetate fraction Substances 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000006260 foam Substances 0.000 description 1
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
238000001640 fractional crystallisation Methods 0.000 description 1
150000002240 furans Chemical class 0.000 description 1
210000004211 gastric acid Anatomy 0.000 description 1
238000011554 guinea pig model Methods 0.000 description 1
125000001188 haloalkyl group Chemical group 0.000 description 1
208000019622 heart disease Diseases 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
230000001631 hypertensive effect Effects 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
208000030603 inherited susceptibility to asthma Diseases 0.000 description 1
238000007918 intramuscular administration Methods 0.000 description 1
238000010255 intramuscular injection Methods 0.000 description 1
239000007927 intramuscular injection Substances 0.000 description 1
238000010253 intravenous injection Methods 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
239000003456 ion exchange resin Substances 0.000 description 1
229920003303 ion-exchange polymer Polymers 0.000 description 1
QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
230000000670 limiting effect Effects 0.000 description 1
125000005647 linker group Chemical group 0.000 description 1
150000002632 lipids Chemical class 0.000 description 1
210000004072 lung Anatomy 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
238000012423 maintenance Methods 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-N methanesulfonic acid Substances CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
PXGWESGJXYODOO-UHFFFAOYSA-N methyl 3-fluoro-2-methoxybenzoate Chemical compound COC(=O)C1=CC=CC(F)=C1OC PXGWESGJXYODOO-UHFFFAOYSA-N 0.000 description 1
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
206010062198 microangiopathy Diseases 0.000 description 1
206010027599 migraine Diseases 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
210000003205 muscle Anatomy 0.000 description 1
208000010125 myocardial infarction Diseases 0.000 description 1
208000031225 myocardial ischemia Diseases 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
229940049964 oleate Drugs 0.000 description 1
DBSMLQTUDJVICQ-CJODITQLSA-N onametostat Chemical compound NC1=C2C=CN([C@@H]3C[C@H](CCC4=CC=C5C=C(Br)C(N)=NC5=C4)[C@@H](O)[C@H]3O)C2=NC=N1 DBSMLQTUDJVICQ-CJODITQLSA-N 0.000 description 1
210000000056 organ Anatomy 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
229960001412 pentobarbital Drugs 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
239000012071 phase Substances 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
239000002571 phosphodiesterase inhibitor Substances 0.000 description 1
229910000073 phosphorus hydride Inorganic materials 0.000 description 1
150000003053 piperidines Chemical class 0.000 description 1
210000002381 plasma Anatomy 0.000 description 1
239000000106 platelet aggregation inhibitor Substances 0.000 description 1
210000004623 platelet-rich plasma Anatomy 0.000 description 1
229920000223 polyglycerol Polymers 0.000 description 1
239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 1
235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
229940068968 polysorbate 80 Drugs 0.000 description 1
229920000053 polysorbate 80 Polymers 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
235000015497 potassium bicarbonate Nutrition 0.000 description 1
229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
239000011736 potassium bicarbonate Substances 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
235000011181 potassium carbonates Nutrition 0.000 description 1
229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
230000002265 prevention Effects 0.000 description 1
239000000047 product Substances 0.000 description 1
230000000069 prophylactic effect Effects 0.000 description 1
229940127293 prostanoid Drugs 0.000 description 1
150000003814 prostanoids Chemical class 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
230000002829 reductive effect Effects 0.000 description 1
230000000284 resting effect Effects 0.000 description 1
238000002390 rotary evaporation Methods 0.000 description 1
208000013220 shortness of breath Diseases 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000011775 sodium fluoride Substances 0.000 description 1
235000013024 sodium fluoride Nutrition 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
239000001593 sorbitan monooleate Substances 0.000 description 1
235000011069 sorbitan monooleate Nutrition 0.000 description 1
229940035049 sorbitan monooleate Drugs 0.000 description 1
229960005078 sorbitan sesquioleate Drugs 0.000 description 1
229940083466 soybean lecithin Drugs 0.000 description 1
239000008347 soybean phospholipid Substances 0.000 description 1
230000003595 spectral effect Effects 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
239000008174 sterile solution Substances 0.000 description 1
150000003431 steroids Chemical class 0.000 description 1
239000012258 stirred mixture Substances 0.000 description 1
210000002784 stomach Anatomy 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000003107 substituted aryl group Chemical group 0.000 description 1
229940014800 succinic anhydride Drugs 0.000 description 1
HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
239000000829 suppository Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
230000035488 systolic blood pressure Effects 0.000 description 1
239000007916 tablet composition Substances 0.000 description 1
201000010875 transient cerebral ischemia Diseases 0.000 description 1
238000002054 transplantation Methods 0.000 description 1
MDJHNFZNJNDPTM-UHFFFAOYSA-M trimethyl(1-phenylethyl)azanium;hydroxide Chemical compound [OH-].C[N+](C)(C)C(C)C1=CC=CC=C1 MDJHNFZNJNDPTM-UHFFFAOYSA-M 0.000 description 1
238000001665 trituration Methods 0.000 description 1
208000019553 vascular disease Diseases 0.000 description 1
229940124549 vasodilator Drugs 0.000 description 1
239000003071 vasodilator agent Substances 0.000 description 1
230000035899 viability Effects 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/04—1,3-Dioxanes; Hydrogenated 1,3-dioxanes
- C07D319/06—1,3-Dioxanes; Hydrogenated 1,3-dioxanes not condensed with other rings
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/08—Vasodilators for multiple indications
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Heart & Thoracic Surgery (AREA)
Cardiology (AREA)
Diabetes (AREA)
Hematology (AREA)
Urology & Nephrology (AREA)
Vascular Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Plural Heterocyclic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
Medicinal Preparation (AREA)
Liquid Crystal Substances (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

DD86290093A 1985-05-10 1986-05-09 Verfahren zur herstellung von 2,4-diphenyl-1,3-dioxian-derivaten DD251749A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB858511890A GB8511890D0 (en)	1985-05-10	1985-05-10	Benzene derivatives

Publications (1)

Publication Number	Publication Date
DD251749A5 true DD251749A5 (de)	1987-11-25

Family

ID=10578944

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD86290093A DD251749A5 (de)	1985-05-10	1986-05-09	Verfahren zur herstellung von 2,4-diphenyl-1,3-dioxian-derivaten

Country Status (22)

Country	Link
US (2)	US4775685A (fr)
EP (1)	EP0201354B1 (fr)
JP (1)	JPS6212772A (fr)
KR (1)	KR860009003A (fr)
AT (1)	ATE56716T1 (fr)
AU (1)	AU583375B2 (fr)
CA (1)	CA1284330C (fr)
DD (1)	DD251749A5 (fr)
DE (1)	DE3674240D1 (fr)
DK (1)	DK164164C (fr)
ES (4)	ES8708221A1 (fr)
FI (1)	FI84602C (fr)
GB (2)	GB8511890D0 (fr)
GR (1)	GR861210B (fr)
HU (1)	HU198467B (fr)
IL (1)	IL78776A (fr)
NO (1)	NO169840C (fr)
NZ (1)	NZ216112A (fr)
PH (1)	PH23667A (fr)
PT (1)	PT82546B (fr)
ZA (1)	ZA863096B (fr)
ZW (1)	ZW9386A1 (fr)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
HU198706B (en) *	1985-05-10	1989-11-28	Ici Plc	Process for producing 1,3-dioxan-ethers and pharmaceutical compositions containing them
GB8511891D0 (en) *	1985-05-10	1985-06-19	Ici Plc	Alkenoic acids
GB8626297D0 (en) *	1986-11-04	1986-12-03	Ici Plc	Pharmaceutical compositions
GB8709794D0 (en) *	1987-04-24	1987-05-28	Ici Plc	Heterocyclic acids
US5248780A (en) *	1988-02-16	1993-09-28	Imperial Chemical Industries, Plc	Pyridyl substituted alkenoic acid derivatives
GB8901201D0 (en) *	1988-02-16	1989-03-15	Ici Plc	Pyridine derivatives
GB8814340D0 (en) *	1988-06-16	1988-07-20	Ici Plc	Process
GB9021571D0 (en) *	1990-10-04	1990-11-21	Ici Plc	Heterocyclic acids
JP2009523781A (ja) *	2006-01-18	2009-06-25	エヴォルヴァエスアー	Ｐｐａｒ調節因子
JP2010516702A (ja) *	2007-01-18	2010-05-20	エヴォルヴァエスアー	置換１，３−ジオキサンのプロドラッグおよびそれらの使用
US20100273824A1 (en) *	2007-01-18	2010-10-28	Evolva Sa	Substituted 1,3-dioxanes and their uses

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB8310407D0 (en) *	1982-05-12	1983-05-25	Ici Plc	1 3 - dioxan -5- ylalkenoic acids
GB8330120D0 (en) *	1983-11-11	1983-12-21	Ici Plc	Chemical process

1985
- 1985-05-10 GB GB858511890A patent/GB8511890D0/en active Pending
1986
- 1986-04-17 GB GB868609451A patent/GB8609451D0/en active Pending
- 1986-04-23 PH PH33695A patent/PH23667A/en unknown
- 1986-04-24 ZA ZA863096A patent/ZA863096B/xx unknown
- 1986-04-28 ZW ZW93/86A patent/ZW9386A1/xx unknown
- 1986-05-02 AU AU57044/86A patent/AU583375B2/en not_active Ceased
- 1986-05-07 HU HU861875A patent/HU198467B/hu not_active IP Right Cessation
- 1986-05-09 DD DD86290093A patent/DD251749A5/de not_active IP Right Cessation
- 1986-05-09 KR KR1019860003597A patent/KR860009003A/ko not_active Ceased
- 1986-05-09 PT PT82546A patent/PT82546B/pt not_active IP Right Cessation
- 1986-05-09 AT AT86303562T patent/ATE56716T1/de not_active IP Right Cessation
- 1986-05-09 US US06/861,329 patent/US4775685A/en not_active Expired - Lifetime
- 1986-05-09 ES ES554826A patent/ES8708221A1/es not_active Expired
- 1986-05-09 GR GR861210A patent/GR861210B/el unknown
- 1986-05-09 DE DE8686303562T patent/DE3674240D1/de not_active Expired - Lifetime
- 1986-05-09 JP JP61105049A patent/JPS6212772A/ja active Pending
- 1986-05-09 CA CA000508782A patent/CA1284330C/fr not_active Expired - Lifetime
- 1986-05-09 FI FI861949A patent/FI84602C/fi not_active IP Right Cessation
- 1986-05-09 DK DK216286A patent/DK164164C/da not_active IP Right Cessation
- 1986-05-09 NO NO861869A patent/NO169840C/no unknown
- 1986-05-09 EP EP86303562A patent/EP0201354B1/fr not_active Expired - Lifetime
- 1986-05-09 NZ NZ216112A patent/NZ216112A/xx unknown
- 1986-05-13 IL IL78776A patent/IL78776A/xx not_active IP Right Cessation
1987
- 1987-06-16 ES ES557601A patent/ES8800193A1/es not_active Expired
- 1987-06-16 ES ES557599A patent/ES8801812A1/es not_active Expired
- 1987-06-16 ES ES557600A patent/ES8801813A1/es not_active Expired
1988
- 1988-07-13 US US07/218,251 patent/US4895962A/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
JPS6212772A (ja)	1987-01-21
HU198467B (en)	1989-10-30
EP0201354B1 (fr)	1990-09-19
ES8800193A1 (es)	1987-10-16
DK216286A (da)	1986-11-11
NO169840B (no)	1992-05-04
DK216286D0 (da)	1986-05-09
FI84602B (fi)	1991-09-13
DE3674240D1 (en)	1990-10-25
ZW9386A1 (en)	1987-11-25
AU5704486A (en)	1986-11-13
ES557600A0 (es)	1988-02-16
ES8801812A1 (es)	1988-02-16
IL78776A (en)	1990-04-29
FI84602C (fi)	1991-12-27
ES8708221A1 (es)	1987-10-01
NO861869L (no)	1986-11-11
DK164164C (da)	1992-10-26
ES8801813A1 (es)	1988-02-16
ATE56716T1 (de)	1990-10-15
ES557599A0 (es)	1988-02-16
EP0201354A3 (en)	1987-04-01
NO169840C (no)	1992-08-12
ES557601A0 (es)	1987-10-16
GB8609451D0 (en)	1986-05-21
AU583375B2 (en)	1989-04-27
FI861949A0 (fi)	1986-05-09
GB8511890D0 (en)	1985-06-19
NZ216112A (en)	1989-04-26
ES554826A0 (es)	1987-10-01
HUT40794A (en)	1987-02-27
FI861949L (fi)	1986-11-11
US4775685A (en)	1988-10-04
PT82546A (en)	1986-06-01
CA1284330C (fr)	1991-05-21
EP0201354A2 (fr)	1986-11-12
US4895962A (en)	1990-01-23
PH23667A (en)	1989-09-27
ZA863096B (en)	1986-12-30
GR861210B (en)	1986-08-29
DK164164B (da)	1992-05-18
PT82546B (pt)	1988-08-17
KR860009003A (ko)	1986-12-19

Legal Events

Date	Code	Title	Description
1994-05-05	ENJ	Ceased due to non-payment of renewal fee

Publication	Publication Date	Title
CA1267417A (fr)	1990-04-03	2,5-diaryltetrahydrofuranes et leurs analogues, antagonistes du facteur d'activation plaquettaire
DE68926144T2 (de)	1996-10-17	Pyridinderivate
DD219769A5 (de)	1985-03-13	Verfahren zur herstellung von 1,3-dioxan-5-yl-alkansaeure-derivaten
DE60103927T2 (de)	2005-06-23	Piperazinderivate, deren Herstellung und deren Verwendung in der Behandlung von Störungen des Zentralnervensystems
DE69132167T2 (de)	2000-12-14	Kondensierte benzoxa-ringverbindung, deren herstellung sowie diese enthaltendes arzneimittel
DE69008205T2 (de)	1994-10-06	Abkömmlinge von Benzocycloalkenyldihydroxyalkansäuren, Verfahren zu deren Herstellung und diese enthaltende Pharmazeutika.
DE3884133T2 (de)	1994-02-03	Antihypertensive Benzopyran-Derivate.
DD251749A5 (de)	1987-11-25	Verfahren zur herstellung von 2,4-diphenyl-1,3-dioxian-derivaten
EP0025192B1 (fr)	1983-05-11	Acides oxiranne-carboxyliques substitués, procédé pour leur préparation, leur utilisation et médicaments les contenant
DE3411993A1 (de)	1985-10-10	Substituierte benzopyrane, verfahren zu ihrer herstellung sowie ihre verwendung in arzneimittel
DE69405624T2 (de)	1998-01-15	Pharmazeutische Verbindungen
DE60121809T2 (de)	2007-02-01	Materialien und verfahren zur herstellung von stilbenen
DE3782396T2 (de)	1993-07-08	Pharmazeutische zusammensetzungen, enthaltend ein 2,4-diphenyl-1,3-dioxane derivat und einen inhibitor des thromboxan a2 synthese.
EP0539803B1 (fr)	1999-01-07	Triazaspirodecanone-méthyl-chromanes pour le traitement des maladies du système nerveux central
DE3685775T2 (de)	1993-01-21	Alkenderivate.
DE3874394T2 (de)	1993-02-25	1,3-dioxane.
DE69130266T2 (de)	1999-03-18	Optisch wirksame Alkylendioxybenzolderivate und ihre Verwendung als Arzneimittel
US4772625A (en)	1988-09-20	1,3-dioxan-5-yl-hexenoic acids
DE68917170T2 (de)	1994-12-15	Pyridin-Derivate.
CH619208A5 (fr)	1980-09-15
DD242804A5 (de)	1987-02-11	Verfahren zur herstellung von dihydropyridinderivaten
DE69205886T2 (de)	1996-06-13	Benzopyranderivate und Verfahren zu deren Herstellung.
JPS62273973A (ja)	1987-11-28	スルホナミド誘導体、その製法及び該誘導体を含有するトロンボキサンａ↓２拮抗剤
EP0030030A1 (fr)	1981-06-10	Dérivés du 2-aminoéthanol, procédés pour leur préparation, préparations pharmaceutiques contenant de tels composés et utilisation de ces dernières
HU198468B (en)	1989-10-30	Process for producing 1,3-dioxane derivative and pharmaceutical compositions comprising the compound