JPS63501293A - アミド誘導体 - Google Patents

アミド誘導体

Info

Publication number: JPS63501293A
Authority: JP; Japan
Prior art keywords: formula; methyl; group; compound; pharmaceutically acceptable
Prior art date: 1985-11-12
Legal status (The legal status 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 status listed.): Pending

Application number

JP61505873A

Other languages

English (en)

Japanese (ja)

Inventor

スミサーズ，マイケル　ジエームズ

Original Assignee

インペリアル　ケミカル　インダストリ−ズ　ピ−エルシ−

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.)

1985-11-12

Filing date

1986-11-06

Publication date

1988-05-19

1986-11-06 Application filed by インペリアル　ケミカル　インダストリ−ズ　ピ−エルシ− filed Critical インペリアル　ケミカル　インダストリ−ズ　ピ−エルシ−

1988-05-19 Publication of JPS63501293A publication Critical patent/JPS63501293A/ja

Status Pending legal-status Critical Current

Links

150000001408 amides Chemical class 0.000 title claims description 5
150000001875 compounds Chemical class 0.000 claims description 44
-1 chloro, bromo, Methyl Chemical group 0.000 claims description 24
150000003839 salts Chemical class 0.000 claims description 23
125000000217 alkyl group Chemical group 0.000 claims description 19
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
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 claims description 17
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 16
238000000034 method Methods 0.000 claims description 16
239000000203 mixture Substances 0.000 claims description 14
239000002253 acid Substances 0.000 claims description 13
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
239000007858 starting material Substances 0.000 claims description 10
239000000126 substance Substances 0.000 claims description 10
125000001424 substituent group Chemical group 0.000 claims description 10
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 9
125000006239 protecting group Chemical group 0.000 claims description 9
239000003085 diluting agent Substances 0.000 claims description 8
239000002585 base Chemical group 0.000 claims description 7
239000008194 pharmaceutical composition Substances 0.000 claims description 7
229940124530 sulfonamide Drugs 0.000 claims description 7
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
125000003545 alkoxy group Chemical group 0.000 claims description 6
125000001246 bromo group Chemical group Br* 0.000 claims description 6
150000001768 cations Chemical class 0.000 claims description 6
125000001309 chloro group Chemical group Cl* 0.000 claims description 6
125000004093 cyano group Chemical group *C#N 0.000 claims description 6
125000001153 fluoro group Chemical group F* 0.000 claims description 6
125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims description 6
150000003456 sulfonamides Chemical class 0.000 claims description 6
BZEUYEFVVDTLOD-SNAWJCMRSA-N (e)-hex-2-enamide Chemical compound CCC\C=C\C(N)=O BZEUYEFVVDTLOD-SNAWJCMRSA-N 0.000 claims description 5
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 4
238000006243 chemical reaction Methods 0.000 claims description 4
150000002373 hemiacetals Chemical class 0.000 claims description 4
238000004519 manufacturing process Methods 0.000 claims description 4
150000002989 phenols Chemical class 0.000 claims description 4
229910052783 alkali metal Inorganic materials 0.000 claims description 3
125000000532 dioxanyl group Chemical group 0.000 claims description 3
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
239000000546 pharmaceutical excipient Substances 0.000 claims description 3
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 claims description 2
239000004480 active ingredient Substances 0.000 claims description 2
229910052784 alkaline earth metal Inorganic materials 0.000 claims description 2
AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 claims description 2
150000001412 amines Chemical class 0.000 claims description 2
150000003863 ammonium salts Chemical class 0.000 claims description 2
125000003118 aryl group Chemical group 0.000 claims description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
239000003153 chemical reaction reagent Substances 0.000 claims description 2
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
239000003112 inhibitor Substances 0.000 claims description 2
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims 2
230000015572 biosynthetic process Effects 0.000 claims 1
238000003786 synthesis reaction Methods 0.000 claims 1
GEGIENATMYITAP-UHFFFAOYSA-N trifluoro(nitro)methane Chemical compound [O-][N+](=O)C(F)(F)F GEGIENATMYITAP-UHFFFAOYSA-N 0.000 claims 1
238000012360 testing method Methods 0.000 description 22
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 19
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 11
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 8
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
229960000583 acetic acid Drugs 0.000 description 8
239000000243 solution Substances 0.000 description 8
239000002904 solvent Substances 0.000 description 8
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
230000000694 effects Effects 0.000 description 7
238000011282 treatment Methods 0.000 description 7
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
241001465754 Metazoa Species 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
239000000284 extract Substances 0.000 description 6
239000003921 oil Substances 0.000 description 6
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
238000007796 conventional method Methods 0.000 description 5
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 5
239000003814 drug Substances 0.000 description 5
235000019439 ethyl acetate Nutrition 0.000 description 5
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
241000700159 Rattus Species 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
230000003042 antagnostic effect Effects 0.000 description 4
230000008485 antagonism Effects 0.000 description 4
239000002775 capsule Substances 0.000 description 4
201000010099 disease Diseases 0.000 description 4
239000000543 intermediate Substances 0.000 description 4
229910052943 magnesium sulfate Inorganic materials 0.000 description 4
235000019341 magnesium sulphate Nutrition 0.000 description 4
JMANVNJQNLATNU-UHFFFAOYSA-N oxalonitrile Chemical compound N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 description 4
241000282472 Canis lupus familiaris Species 0.000 description 3
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 3
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
241000283973 Oryctolagus cuniculus Species 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
231100000673 dose–response relationship Toxicity 0.000 description 3
229940079593 drug Drugs 0.000 description 3
239000000463 material Substances 0.000 description 3
230000003278 mimic effect Effects 0.000 description 3
229910052703 rhodium Inorganic materials 0.000 description 3
238000003756 stirring Methods 0.000 description 3
239000000725 suspension Substances 0.000 description 3
CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 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
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
206010006482 Bronchospasm Diseases 0.000 description 2
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
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 2
238000003820 Medium-pressure liquid chromatography Methods 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 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
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
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
150000001241 acetals Chemical class 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
239000000556 agonist Substances 0.000 description 2
239000002220 antihypertensive agent Substances 0.000 description 2
229940127088 antihypertensive drug Drugs 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
229910052786 argon Inorganic materials 0.000 description 2
210000004369 blood Anatomy 0.000 description 2
239000008280 blood Substances 0.000 description 2
230000036772 blood pressure Effects 0.000 description 2
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239000003795 chemical substances by application Substances 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
230000001186 cumulative effect Effects 0.000 description 2
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 2
239000002552 dosage form Substances 0.000 description 2
150000002170 ethers Chemical class 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
229910052739 hydrogen Inorganic materials 0.000 description 2
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
229910000041 hydrogen chloride Inorganic materials 0.000 description 2
238000001990 intravenous administration Methods 0.000 description 2
210000004072 lung Anatomy 0.000 description 2
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
238000012986 modification Methods 0.000 description 2
230000004048 modification Effects 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
239000011591 potassium Substances 0.000 description 2
230000008569 process Effects 0.000 description 2
229910052705 radium Inorganic materials 0.000 description 2
230000004044 response Effects 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000011734 sodium Substances 0.000 description 2
PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 2
239000012312 sodium hydride Substances 0.000 description 2
229910000104 sodium hydride Inorganic materials 0.000 description 2
239000007787 solid Substances 0.000 description 2
208000010110 spontaneous platelet aggregation Diseases 0.000 description 2
210000002784 stomach Anatomy 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 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
230000001225 therapeutic effect Effects 0.000 description 2
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
NIONDZDPPYHYKY-SNAWJCMRSA-N (2E)-hexenoic acid Chemical compound CCC\C=C\C(O)=O NIONDZDPPYHYKY-SNAWJCMRSA-N 0.000 description 1
ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 description 1
VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 1
125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 description 1
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238000000354 decomposition reaction Methods 0.000 description 1
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235000011180 diphosphates Nutrition 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
GUVUOGQBMYCBQP-UHFFFAOYSA-N dmpu Chemical compound CN1CCCN(C)C1=O GUVUOGQBMYCBQP-UHFFFAOYSA-N 0.000 description 1
239000002702 enteric coating Substances 0.000 description 1
238000009505 enteric coating Methods 0.000 description 1
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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 description 1
DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 1
125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 description 1
125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
238000011156 evaluation Methods 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000001914 filtration Methods 0.000 description 1
238000001640 fractional crystallisation Methods 0.000 description 1
IRSCQMHQWWYFCW-UHFFFAOYSA-N ganciclovir Chemical compound O=C1NC(N)=NC2=C1N=CN2COC(CO)CO IRSCQMHQWWYFCW-UHFFFAOYSA-N 0.000 description 1
229960002963 ganciclovir Drugs 0.000 description 1
239000007789 gas Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
238000007429 general method Methods 0.000 description 1
238000011554 guinea pig model Methods 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
150000004677 hydrates Chemical class 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
230000003301 hydrolyzing effect Effects 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
230000006698 induction Effects 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
208000030603 inherited susceptibility to asthma Diseases 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
229910052500 inorganic mineral Inorganic materials 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
210000004731 jugular vein Anatomy 0.000 description 1
239000008101 lactose Substances 0.000 description 1
150000002632 lipids Chemical class 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000006193 liquid solution Substances 0.000 description 1
239000006194 liquid suspension Substances 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
229910003002 lithium salt Inorganic materials 0.000 description 1
159000000002 lithium salts Chemical class 0.000 description 1
238000005259 measurement Methods 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 description 1
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
206010027599 migraine Diseases 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
239000011707 mineral Substances 0.000 description 1
230000002107 myocardial effect Effects 0.000 description 1
208000031225 myocardial ischemia Diseases 0.000 description 1
PBMIETCUUSQZCG-UHFFFAOYSA-N n'-cyclohexylmethanediimine Chemical compound N=C=NC1CCCCC1 PBMIETCUUSQZCG-UHFFFAOYSA-N 0.000 description 1
239000006199 nebulizer Substances 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
150000002894 organic compounds Chemical class 0.000 description 1
229940094443 oxytocics prostaglandins Drugs 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
239000002504 physiological saline solution Substances 0.000 description 1
210000004623 platelet-rich plasma Anatomy 0.000 description 1
LJCNRYVRMXRIQR-OLXYHTOASA-L potassium sodium L-tartrate Chemical compound [Na+].[K+].[O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O LJCNRYVRMXRIQR-OLXYHTOASA-L 0.000 description 1
WSTGIAUNSWPOJM-UHFFFAOYSA-N potassium tert-butylazanide Chemical compound CC(C)(C)[NH-].[K+] WSTGIAUNSWPOJM-UHFFFAOYSA-N 0.000 description 1
239000000843 powder Substances 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
230000002315 pressor effect Effects 0.000 description 1
230000002265 prevention Effects 0.000 description 1
150000003180 prostaglandins Chemical class 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
238000002390 rotary evaporation Methods 0.000 description 1
229910052701 rubidium Inorganic materials 0.000 description 1
229910000077 silane Inorganic materials 0.000 description 1
239000011775 sodium fluoride Substances 0.000 description 1
235000013024 sodium fluoride Nutrition 0.000 description 1
239000001476 sodium potassium tartrate Substances 0.000 description 1
235000011006 sodium potassium tartrate Nutrition 0.000 description 1
159000000000 sodium salts Chemical class 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
239000010902 straw Substances 0.000 description 1
125000003107 substituted aryl group Chemical group 0.000 description 1
HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
150000003462 sulfoxides Chemical class 0.000 description 1
239000013589 supplement Substances 0.000 description 1
239000000829 suppository Substances 0.000 description 1
230000001629 suppression Effects 0.000 description 1
229940127230 sympathomimetic drug Drugs 0.000 description 1
230000035488 systolic blood pressure Effects 0.000 description 1
239000003826 tablet Substances 0.000 description 1
DLNOIRAFPPLAPE-UHFFFAOYSA-L tetramethylazanium dihydroxide Chemical compound [OH-].[OH-].C[N+](C)(C)C.C[N+](C)(C)C DLNOIRAFPPLAPE-UHFFFAOYSA-L 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
210000005090 tracheal smooth muscle Anatomy 0.000 description 1
238000012546 transfer Methods 0.000 description 1
201000010875 transient cerebral ischemia Diseases 0.000 description 1
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
229960004418 trolamine Drugs 0.000 description 1
WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
229910052721 tungsten Inorganic materials 0.000 description 1
239000010937 tungsten Substances 0.000 description 1
230000002792 vascular Effects 0.000 description 1
208000019553 vascular disease Diseases 0.000 description 1
210000005166 vasculature Anatomy 0.000 description 1
239000005526 vasoconstrictor agent Substances 0.000 description 1
229940124549 vasodilator Drugs 0.000 description 1
239000003071 vasodilator agent Substances 0.000 description 1
210000003462 vein Anatomy 0.000 description 1
230000035899 viability Effects 0.000 description 1
239000000052 vinegar Substances 0.000 description 1
235000021419 vinegar Nutrition 0.000 description 1
238000010792 warming Methods 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Landscapes

Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)

JP61505873A 1985-11-12 1986-11-06 アミド誘導体 Pending JPS63501293A (ja)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
GB8527862		1985-11-12
GB858527862A GB8527862D0 (en)	1985-11-12	1985-11-12	Ether derivatives
GB8611174		1986-05-08

Publications (1)

Publication Number	Publication Date
JPS63501293A true JPS63501293A (ja)	1988-05-19

Family

ID=10588096

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP61505873A Pending JPS63501293A (ja)	1985-11-12	1986-11-06	アミド誘導体

Country Status (6)

Country	Link
JP (1)	JPS63501293A (de)
DD (1)	DD259864A5 (de)
GB (1)	GB8527862D0 (de)
PH (1)	PH23183A (de)
SU (1)	SU1600629A3 (de)
ZA (1)	ZA868508B (de)

1985
- 1985-11-12 GB GB858527862A patent/GB8527862D0/en active Pending
1986
- 1986-11-05 PH PH34440A patent/PH23183A/en unknown
- 1986-11-06 DD DD29600886A patent/DD259864A5/de not_active IP Right Cessation
- 1986-11-06 JP JP61505873A patent/JPS63501293A/ja active Pending
- 1986-11-07 ZA ZA868508A patent/ZA868508B/xx unknown
- 1986-11-11 SU SU864028607A patent/SU1600629A3/ru active

Also Published As

Publication number	Publication date
ZA868508B (en)	1987-06-24
GB8527862D0 (en)	1985-12-18
SU1600629A3 (ru)	1990-10-15
DD259864A5 (de)	1988-09-07
PH23183A (en)	1989-05-29

Publication	Publication Date	Title
US4567197A (en)	1986-01-28	1,3-Dioxan-5-ylalkenoic acids
JP2013508385A (ja)	2013-03-07	治療上有用な、受容体修飾薬としてのクマリン化合物
EP0351255B1 (de)	1993-10-13	2-[(4-Piperidinyl)methyl]-1,2,3,4-tetrahydroisochinolin-Derivate, ihre Herstellung und ihre therapeutische Verwendung
EP0201354B1 (de)	1990-09-19	2,4-Diphenyl-1,3-dioxane
FR2611139A1 (fr)	1988-08-26	Medicaments a base de nouveaux derives oxy-5 du tetrahydrofurane
EP0223518B1 (de)	1990-09-26	Amidderivate
EP0266980B1 (de)	1992-10-28	Pharmazeutische Zusammensetzungen, enthaltend ein 2,4-diphenyl-1,3-dioxane derivat und einen Inhibitor des Thromboxan A2 Synthese
JPS63501293A (ja)	1988-05-19	アミド誘導体
PL184060B1 (pl)	2002-08-30	Podstawione związki fenylowe do zastosowania jako środki antagonistyczne endoteliny
JP2812697B2 (ja)	1998-10-22	１，３―ジオキサンアルケン酸誘導体、その製造方法、中間体、および虚血性心臓、大悩血管性、喘息性および／または炎症性疾患の治療用薬学的組成物
US4831046A (en)	1989-05-16	Tetrazole derivatives of 1,3-dioxane and thromboxane A2 antigonizing use thereof
EP0246002B1 (de)	1991-11-27	Alkenamid-Derivate
JPS6212775A (ja)	1987-01-21	〔５，６〕‐シス‐１，３‐オキサチアン誘導体、その製造法、および該化合物を含有する医薬組成物
JPS62215584A (ja)	1987-09-22	１，３−ジオキサンヘキセン酸、その製造法、および該化合物を含有する医薬組成物
US5248780A (en)	1993-09-28	Pyridyl substituted alkenoic acid derivatives
JPS61280487A (ja)	1986-12-11	フルオロアルカン誘導体、その製造法およびこの誘導体を含有する肺および血管疾病を治療する医薬組成物
JPS63130531A (ja)	1988-06-02	トロンボキサンａ↓２又は関連プロスタノイド収縮物質により誘起される疾病の治療及び予防用の医薬組成物
JPS6216475A (ja)	1987-01-24	〔２，４，５−シス〕−ジオキサン、その製法及びこれを含有する医薬組成物
FR2539127A1 (fr)	1984-07-13	Nouveaux derives du 4h-1,2,4-triazole, leur procede de preparation et leur application comme medicaments
RU2040525C1 (ru)	1995-07-25	1,3-дииоксаноновые производные алкеновой кислоты или их фармацевтически приемлемая соль
JPS61280488A (ja)	1986-12-11	オクテン酸誘導体、その製造法およびこの誘導体を含有する肺および血管疾病を治療する医薬組成物
JPH03120283A (ja)	1991-05-22	ジオキシノキノリン誘導体および該化合物を有効成分とする医薬組成物
FR2634205A2 (fr)	1990-01-19	Derives de me thyl-4 ((piperidinyl-4)methyl)-2 tetrahydro-1,2,3,4 isoquinoleine, leur preparation et leur application en therapeutique