NL8004609A - Carbonzuuramiden en farmaceutisch preparaat alsmede werkwijze voor het bereiden daarvan. - Google Patents

Carbonzuuramiden en farmaceutisch preparaat alsmede werkwijze voor het bereiden daarvan. Download PDF

Info

Publication number: NL8004609A
Authority: NL; Netherlands
Prior art keywords: compound; formula; morpholine; group; tetramethyl
Prior art date: 1979-08-14

Application number

NL8004609A

Other languages

English (en)

Dutch (nl)

Original Assignee

Eisai Co Ltd

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.)

1979-08-14

Filing date

1980-08-14

Publication date

1981-02-17

1979-08-14 Priority claimed from JP10274779A external-priority patent/JPS5626852A/ja

1979-08-28 Priority claimed from JP10866879A external-priority patent/JPS5632442A/ja

1980-08-14 Application filed by Eisai Co Ltd filed Critical Eisai Co Ltd

1981-02-17 Publication of NL8004609A publication Critical patent/NL8004609A/nl

Links

238000000034 method Methods 0.000 title claims description 20
239000000825 pharmaceutical preparation Substances 0.000 title description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 title 1
150000001875 compounds Chemical class 0.000 claims description 135
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 36
-1 hexadecaenoyl Chemical group 0.000 claims description 16
125000004432 carbon atom Chemical group C* 0.000 claims description 14
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
239000003153 chemical reaction reagent Substances 0.000 claims description 8
150000001408 amides Chemical class 0.000 claims description 7
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
125000000217 alkyl group Chemical group 0.000 claims description 6
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 6
208000019423 liver disease Diseases 0.000 claims description 6
230000005976 liver dysfunction Effects 0.000 claims description 6
125000003710 aryl alkyl group Chemical group 0.000 claims description 4
125000005843 halogen group Chemical group 0.000 claims description 4
125000005842 heteroatom Chemical group 0.000 claims description 3
125000000623 heterocyclic group Chemical group 0.000 claims description 3
229920001550 polyprenyl Polymers 0.000 claims description 3
125000001185 polyprenyl group Polymers 0.000 claims description 3
IVAXYKPQCGJMHY-UHFFFAOYSA-N 3,7,11-trimethyl-1-morpholin-4-yldodeca-2,6,10-trien-1-one Chemical compound CC(C)=CCCC(C)=CCCC(C)=CC(=O)N1CCOCC1 IVAXYKPQCGJMHY-UHFFFAOYSA-N 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims description 2
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 2
239000008194 pharmaceutical composition Substances 0.000 claims description 2
239000004480 active ingredient Substances 0.000 claims 1
125000004429 atom Chemical group 0.000 claims 1
239000000546 pharmaceutical excipient Substances 0.000 claims 1
239000000203 mixture Substances 0.000 description 43
229910052739 hydrogen Inorganic materials 0.000 description 41
229910052757 nitrogen Inorganic materials 0.000 description 41
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 32
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 30
230000015572 biosynthetic process Effects 0.000 description 30
238000003786 synthesis reaction Methods 0.000 description 30
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 29
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 28
239000011541 reaction mixture Substances 0.000 description 27
239000007788 liquid Substances 0.000 description 26
239000002904 solvent Substances 0.000 description 25
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
238000004821 distillation Methods 0.000 description 22
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 20
238000000862 absorption spectrum Methods 0.000 description 20
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 20
239000000243 solution Substances 0.000 description 20
238000001819 mass spectrum Methods 0.000 description 19
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 16
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 15
239000000284 extract Substances 0.000 description 14
229940113083 morpholine Drugs 0.000 description 14
238000004458 analytical method Methods 0.000 description 13
238000004440 column chromatography Methods 0.000 description 13
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
239000000741 silica gel Substances 0.000 description 12
229910002027 silica gel Inorganic materials 0.000 description 12
238000006243 chemical reaction Methods 0.000 description 11
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 10
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 10
239000012312 sodium hydride Substances 0.000 description 10
229910000104 sodium hydride Inorganic materials 0.000 description 10
241000700159 Rattus Species 0.000 description 9
WMFYOYKPJLRMJI-UHFFFAOYSA-N Lercanidipine hydrochloride Chemical compound Cl.COC(=O)C1=C(C)NC(C)=C(C(=O)OC(C)(C)CN(C)CCC(C=2C=CC=CC=2)C=2C=CC=CC=2)C1C1=CC=CC([N+]([O-])=O)=C1 WMFYOYKPJLRMJI-UHFFFAOYSA-N 0.000 description 8
LTUMRKDLVGQMJU-UHFFFAOYSA-N famesylacetone Natural products CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=O LTUMRKDLVGQMJU-UHFFFAOYSA-N 0.000 description 8
LTUMRKDLVGQMJU-IUBLYSDUSA-N farnesyl acetone Chemical compound CC(C)=CCC\C(C)=C\CC\C(C)=C\CCC(C)=O LTUMRKDLVGQMJU-IUBLYSDUSA-N 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
238000000921 elemental analysis Methods 0.000 description 7
239000000377 silicon dioxide Substances 0.000 description 7
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 6
XZXLYGAUEAPJET-UHFFFAOYSA-N 5-amino-3h-1-benzofuran-2-one Chemical compound NC1=CC=C2OC(=O)CC2=C1 XZXLYGAUEAPJET-UHFFFAOYSA-N 0.000 description 6
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
210000000683 abdominal cavity Anatomy 0.000 description 6
239000002253 acid Substances 0.000 description 6
239000003513 alkali Substances 0.000 description 6
238000007796 conventional method Methods 0.000 description 6
229910000033 sodium borohydride Inorganic materials 0.000 description 6
239000012279 sodium borohydride Substances 0.000 description 6
239000000725 suspension Substances 0.000 description 6
108090000608 Phosphoric Monoester Hydrolases Proteins 0.000 description 5
102000004160 Phosphoric Monoester Hydrolases Human genes 0.000 description 5
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 4
229920002261 Corn starch Polymers 0.000 description 4
229920002153 Hydroxypropyl cellulose Polymers 0.000 description 4
101000986989 Naja kaouthia Acidic phospholipase A2 CM-II Proteins 0.000 description 4
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
239000001913 cellulose Substances 0.000 description 4
229920002678 cellulose Polymers 0.000 description 4
239000008120 corn starch Substances 0.000 description 4
239000001863 hydroxypropyl cellulose Substances 0.000 description 4
235000010977 hydroxypropyl cellulose Nutrition 0.000 description 4
230000000873 masking effect Effects 0.000 description 4
238000010898 silica gel chromatography Methods 0.000 description 4
MSSDTZLYNMFTKN-UHFFFAOYSA-N 1-Piperazinecarboxaldehyde Chemical compound O=CN1CCNCC1 MSSDTZLYNMFTKN-UHFFFAOYSA-N 0.000 description 3
WFCSWCVEJLETKA-UHFFFAOYSA-N 2-piperazin-1-ylethanol Chemical compound OCCN1CCNCC1 WFCSWCVEJLETKA-UHFFFAOYSA-N 0.000 description 3
244000215068 Acacia senegal Species 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
229920000084 Gum arabic Polymers 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
239000000205 acacia gum Substances 0.000 description 3
235000010489 acacia gum Nutrition 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
239000008280 blood Substances 0.000 description 3
210000004369 blood Anatomy 0.000 description 3
239000002775 capsule Substances 0.000 description 3
230000000694 effects Effects 0.000 description 3
125000004494 ethyl ester group Chemical group 0.000 description 3
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 3
125000000524 functional group Chemical group 0.000 description 3
229910001507 metal halide Inorganic materials 0.000 description 3
150000005309 metal halides Chemical class 0.000 description 3
229910052760 oxygen Inorganic materials 0.000 description 3
238000006722 reduction reaction Methods 0.000 description 3
239000000126 substance Substances 0.000 description 3
MSWZFWKMSRAUBD-GASJEMHNSA-N 2-amino-2-deoxy-D-galactopyranose Chemical compound N[C@H]1C(O)O[C@H](CO)[C@H](O)[C@@H]1O MSWZFWKMSRAUBD-GASJEMHNSA-N 0.000 description 2
SSXYKBHZZRYLLY-UHFFFAOYSA-N 2-chloro-1,3-oxazole Chemical compound ClC1=NC=CO1 SSXYKBHZZRYLLY-UHFFFAOYSA-N 0.000 description 2
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
125000002373 5 membered heterocyclic group Chemical group 0.000 description 2
125000004070 6 membered heterocyclic group Chemical group 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 2
239000005695 Ammonium acetate Substances 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
102100035861 Cytosolic 5'-nucleotidase 1A Human genes 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
101000802744 Homo sapiens Cytosolic 5'-nucleotidase 1A Proteins 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-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
241001465754 Metazoa Species 0.000 description 2
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
229910021586 Nickel(II) chloride Inorganic materials 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
230000002159 abnormal effect Effects 0.000 description 2
150000008065 acid anhydrides Chemical class 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
125000003545 alkoxy group Chemical group 0.000 description 2
238000010640 amide synthesis reaction Methods 0.000 description 2
229940043376 ammonium acetate Drugs 0.000 description 2
235000019257 ammonium acetate Nutrition 0.000 description 2
239000002585 base Substances 0.000 description 2
MSWZFWKMSRAUBD-UHFFFAOYSA-N beta-D-galactosamine Natural products NC1C(O)OC(CO)C(O)C1O MSWZFWKMSRAUBD-UHFFFAOYSA-N 0.000 description 2
CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 2
239000008116 calcium stearate Substances 0.000 description 2
235000013539 calcium stearate Nutrition 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
JNGZXGGOCLZBFB-IVCQMTBJSA-N compound E Chemical compound N([C@@H](C)C(=O)N[C@@H]1C(N(C)C2=CC=CC=C2C(C=2C=CC=CC=2)=N1)=O)C(=O)CC1=CC(F)=CC(F)=C1 JNGZXGGOCLZBFB-IVCQMTBJSA-N 0.000 description 2
MLIREBYILWEBDM-UHFFFAOYSA-N cyanoacetic acid Chemical compound OC(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-N 0.000 description 2
230000004064 dysfunction Effects 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
ZIUSEGSNTOUIPT-UHFFFAOYSA-N ethyl 2-cyanoacetate Chemical compound CCOC(=O)CC#N ZIUSEGSNTOUIPT-UHFFFAOYSA-N 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
238000001914 filtration Methods 0.000 description 2
239000007903 gelatin capsule Substances 0.000 description 2
FVIZARNDLVOMSU-UHFFFAOYSA-N ginsenoside K Natural products C1CC(C2(CCC3C(C)(C)C(O)CCC3(C)C2CC2O)C)(C)C2C1C(C)(CCC=C(C)C)OC1OC(CO)C(O)C(O)C1O FVIZARNDLVOMSU-UHFFFAOYSA-N 0.000 description 2
208000006454 hepatitis Diseases 0.000 description 2
231100000283 hepatitis Toxicity 0.000 description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
239000005457 ice water Substances 0.000 description 2
210000004185 liver Anatomy 0.000 description 2
QMMRZOWCJAIUJA-UHFFFAOYSA-L nickel dichloride Chemical compound Cl[Ni]Cl QMMRZOWCJAIUJA-UHFFFAOYSA-L 0.000 description 2
IZUPBVBPLAPZRR-UHFFFAOYSA-N pentachlorophenol Chemical compound OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl IZUPBVBPLAPZRR-UHFFFAOYSA-N 0.000 description 2
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000011734 sodium Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
239000000454 talc Substances 0.000 description 2
229910052623 talc Inorganic materials 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
VCGRFBXVSFAGGA-UHFFFAOYSA-N (1,1-dioxo-1,4-thiazinan-4-yl)-[6-[[3-(4-fluorophenyl)-5-methyl-1,2-oxazol-4-yl]methoxy]pyridin-3-yl]methanone Chemical compound CC=1ON=C(C=2C=CC(F)=CC=2)C=1COC(N=C1)=CC=C1C(=O)N1CCS(=O)(=O)CC1 VCGRFBXVSFAGGA-UHFFFAOYSA-N 0.000 description 1
AHKPAGWXYZOZGX-RQZCQDPDSA-N (6e)-3,7,11-trimethyl-1-morpholin-4-yldodeca-6,10-dien-1-one Chemical compound CC(C)=CCCC(/C)=C/CCC(C)CC(=O)N1CCOCC1 AHKPAGWXYZOZGX-RQZCQDPDSA-N 0.000 description 1
FVQMTDGKHQLJTO-NTEUORMPSA-N (6e)-3,7,11-trimethyldodeca-6,10-dienenitrile Chemical compound N#CCC(C)CC\C=C(/C)CCC=C(C)C FVQMTDGKHQLJTO-NTEUORMPSA-N 0.000 description 1
HDAQPCUHLCPEHS-UKTHLTGXSA-N (6e)-3,7,11-trimethyldodeca-6,10-dienoic acid Chemical compound OC(=O)CC(C)CC\C=C(/C)CCC=C(C)C HDAQPCUHLCPEHS-UKTHLTGXSA-N 0.000 description 1
WZZBNLYBHUDSHF-DHLKQENFSA-N 1-[(3s,4s)-4-[8-(2-chloro-4-pyrimidin-2-yloxyphenyl)-7-fluoro-2-methylimidazo[4,5-c]quinolin-1-yl]-3-fluoropiperidin-1-yl]-2-hydroxyethanone Chemical compound CC1=NC2=CN=C3C=C(F)C(C=4C(=CC(OC=5N=CC=CN=5)=CC=4)Cl)=CC3=C2N1[C@H]1CCN(C(=O)CO)C[C@@H]1F WZZBNLYBHUDSHF-DHLKQENFSA-N 0.000 description 1
125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
ABEXEQSGABRUHS-UHFFFAOYSA-N 16-methylheptadecyl 16-methylheptadecanoate Chemical compound CC(C)CCCCCCCCCCCCCCCOC(=O)CCCCCCCCCCCCCCC(C)C ABEXEQSGABRUHS-UHFFFAOYSA-N 0.000 description 1
CDULGHZNHURECF-UHFFFAOYSA-N 2,3-dimethylaniline 2,4-dimethylaniline 2,5-dimethylaniline 2,6-dimethylaniline 3,4-dimethylaniline 3,5-dimethylaniline Chemical group CC1=CC=C(N)C(C)=C1.CC1=CC=C(C)C(N)=C1.CC1=CC(C)=CC(N)=C1.CC1=CC=C(N)C=C1C.CC1=CC=CC(N)=C1C.CC1=CC=CC(C)=C1N CDULGHZNHURECF-UHFFFAOYSA-N 0.000 description 1
UFBJCMHMOXMLKC-UHFFFAOYSA-N 2,4-dinitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O UFBJCMHMOXMLKC-UHFFFAOYSA-N 0.000 description 1
CRYOBSXYQNJFNR-UHFFFAOYSA-N 2-(2,6-dimethylphenyl)acetamide Chemical compound CC1=CC=CC(C)=C1CC(N)=O CRYOBSXYQNJFNR-UHFFFAOYSA-N 0.000 description 1
SPNSSEKVTXYNNH-UHFFFAOYSA-N 2-diethoxyphosphoryl-n,n-dimethylacetamide Chemical compound CCOP(=O)(OCC)CC(=O)N(C)C SPNSSEKVTXYNNH-UHFFFAOYSA-N 0.000 description 1
QPVCUQOSWAXEOQ-UHFFFAOYSA-N 2-diethoxyphosphorylacetamide Chemical compound CCOP(=O)(CC(N)=O)OCC QPVCUQOSWAXEOQ-UHFFFAOYSA-N 0.000 description 1
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
WBJWXIQDBDZMAW-UHFFFAOYSA-N 2-hydroxynaphthalene-1-carbonyl chloride Chemical compound C1=CC=CC2=C(C(Cl)=O)C(O)=CC=C21 WBJWXIQDBDZMAW-UHFFFAOYSA-N 0.000 description 1
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
MFQTXLOKPQSQCV-UHFFFAOYSA-N 3,7,11-trimethyl-1-morpholin-4-yldodecan-1-one Chemical compound CC(C)CCCC(C)CCCC(C)CC(=O)N1CCOCC1 MFQTXLOKPQSQCV-UHFFFAOYSA-N 0.000 description 1
BTJIUGUIPKRLHP-UHFFFAOYSA-N 4-nitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1 BTJIUGUIPKRLHP-UHFFFAOYSA-N 0.000 description 1
QNNFQFRKIOPJRL-UHFFFAOYSA-N 6,10,13-trimethylpentadecane-2,4-dione Chemical compound CC(CC(=O)CC(C)=O)CCCC(CCC(CC)C)C QNNFQFRKIOPJRL-UHFFFAOYSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
229940126062 Compound A Drugs 0.000 description 1
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical group CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 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
206010061218 Inflammation Diseases 0.000 description 1
241000764238 Isis Species 0.000 description 1
RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical group CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 1
208000002720 Malnutrition Diseases 0.000 description 1
AYCPARAPKDAOEN-LJQANCHMSA-N N-[(1S)-2-(dimethylamino)-1-phenylethyl]-6,6-dimethyl-3-[(2-methyl-4-thieno[3,2-d]pyrimidinyl)amino]-1,4-dihydropyrrolo[3,4-c]pyrazole-5-carboxamide Chemical compound C1([C@H](NC(=O)N2C(C=3NN=C(NC=4C=5SC=CC=5N=C(C)N=4)C=3C2)(C)C)CN(C)C)=CC=CC=C1 AYCPARAPKDAOEN-LJQANCHMSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
239000007868 Raney catalyst Substances 0.000 description 1
229910000564 Raney nickel Inorganic materials 0.000 description 1
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
101150094640 Siae gene Proteins 0.000 description 1
229910003524 Sr—H Inorganic materials 0.000 description 1
244000299461 Theobroma cacao Species 0.000 description 1
235000005764 Theobroma cacao ssp. cacao Nutrition 0.000 description 1
235000005767 Theobroma cacao ssp. sphaerocarpum Nutrition 0.000 description 1
241000700605 Viruses Species 0.000 description 1
238000007239 Wittig reaction Methods 0.000 description 1
CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Substances CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
125000005036 alkoxyphenyl group Chemical group 0.000 description 1
125000005907 alkyl ester group Chemical group 0.000 description 1
PYHXGXCGESYPCW-UHFFFAOYSA-N alpha-phenylbenzeneacetic acid Natural products C=1C=CC=CC=1C(C(=O)O)C1=CC=CC=C1 PYHXGXCGESYPCW-UHFFFAOYSA-N 0.000 description 1
230000009435 amidation Effects 0.000 description 1
238000007112 amidation reaction Methods 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
230000037396 body weight Effects 0.000 description 1
235000001046 cacaotero Nutrition 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
238000010531 catalytic reduction reaction Methods 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical class OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 description 1
GVPFVAHMJGGAJG-UHFFFAOYSA-L cobalt dichloride Chemical compound [Cl-].[Cl-].[Co+2] GVPFVAHMJGGAJG-UHFFFAOYSA-L 0.000 description 1
229940125898 compound 5 Drugs 0.000 description 1
239000012050 conventional carrier Substances 0.000 description 1
239000013256 coordination polymer Substances 0.000 description 1
ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 1
IRJGZWIEFFOYJN-UHFFFAOYSA-N copper;pyridine Chemical compound [Cu].C1=CC=NC=C1 IRJGZWIEFFOYJN-UHFFFAOYSA-N 0.000 description 1
230000007850 degeneration Effects 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000010200 folin Substances 0.000 description 1
HNZUNIKWNYHEJJ-FMIVXFBMSA-N geranyl acetone Chemical compound CC(C)=CCC\C(C)=C\CCC(C)=O HNZUNIKWNYHEJJ-FMIVXFBMSA-N 0.000 description 1
HNZUNIKWNYHEJJ-UHFFFAOYSA-N geranyl acetone Natural products CC(C)=CCCC(C)=CCCC(C)=O HNZUNIKWNYHEJJ-UHFFFAOYSA-N 0.000 description 1
LTYRAPJYLUPLCI-UHFFFAOYSA-N glycolonitrile Chemical compound OCC#N LTYRAPJYLUPLCI-UHFFFAOYSA-N 0.000 description 1
239000008187 granular material Substances 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
239000007902 hard capsule Substances 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
125000002768 hydroxyalkyl group Chemical group 0.000 description 1
238000005417 image-selected in vivo spectroscopy Methods 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
230000004054 inflammatory process Effects 0.000 description 1
238000012739 integrated shape imaging system Methods 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
230000003908 liver function Effects 0.000 description 1
231100000053 low toxicity Toxicity 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
235000018343 nutrient deficiency Nutrition 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
231100000614 poison Toxicity 0.000 description 1
239000002574 poison Substances 0.000 description 1
229920000137 polyphosphoric acid Polymers 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
239000000843 powder Substances 0.000 description 1
LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
KOUKXHPPRFNWPP-UHFFFAOYSA-N pyrazine-2,5-dicarboxylic acid;hydrate Chemical compound O.OC(=O)C1=CN=C(C(O)=O)C=N1 KOUKXHPPRFNWPP-UHFFFAOYSA-N 0.000 description 1
229940081974 saccharin Drugs 0.000 description 1
235000019204 saccharin Nutrition 0.000 description 1
239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000007901 soft capsule Substances 0.000 description 1
229940124530 sulfonamide Drugs 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
239000003053 toxin Substances 0.000 description 1
231100000765 toxin Toxicity 0.000 description 1
108700012359 toxins Proteins 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids
- C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/08—Preparation of carboxylic acids or their salts, halides or anhydrides from nitriles
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/58—Preparation of carboxylic acid halides
- C07C51/60—Preparation of carboxylic acid halides by conversion of carboxylic acids or their anhydrides or esters, lactones, salts into halides with the same carboxylic acid part
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
- C07D317/58—Radicals substituted by nitrogen atoms

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Oil, Petroleum & Natural Gas (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

NL8004609A 1979-08-14 1980-08-14 Carbonzuuramiden en farmaceutisch preparaat alsmede werkwijze voor het bereiden daarvan. NL8004609A (nl)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
JP10274779		1979-08-14
JP10274779A JPS5626852A (en)	1979-08-14	1979-08-14	Alpha,beta-dihydropolyprenylcarbonamide
JP10866879		1979-08-28
JP10866879A JPS5632442A (en)	1979-08-28	1979-08-28	Polyprenylcarboxylic acid amide

Publications (1)

Publication Number	Publication Date
NL8004609A true NL8004609A (nl)	1981-02-17

Family

ID=26443426

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL8004609A NL8004609A (nl)	1979-08-14	1980-08-14	Carbonzuuramiden en farmaceutisch preparaat alsmede werkwijze voor het bereiden daarvan.

Country Status (12)

Country	Link
US (2)	US4456603A (fr)
AU (1)	AU531466B2 (fr)
CA (1)	CA1148153A (fr)
CH (1)	CH644582A5 (fr)
DE (1)	DE3030462A1 (fr)
ES (1)	ES494230A0 (fr)
FR (2)	FR2463122A1 (fr)
GB (1)	GB2058782B (fr)
IT (1)	IT1132406B (fr)
NL (1)	NL8004609A (fr)
PH (1)	PH16234A (fr)
SE (2)	SE446977B (fr)

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS5899490A (ja) *	1981-10-19	1983-06-13	Eisai Co Ltd	リン酸アミド誘導体およびその製造方法ならびにそれを含有する医薬
US4564477A (en) *	1982-02-19	1986-01-14	Kuraray Co., Ltd.	Polyprenyl compounds and method of producing the same
JPS58177953A (ja) *	1982-04-13	1983-10-18	Eisai Co Ltd	ポリプレニルカルボン酸アミドおよびその製造方法
JPS591474A (ja) *	1982-06-07	1984-01-06	Nippon Iyakuhin Kogyo Kk	ピペラジン環を有するゲラニルゲラニル酢酸アミド化合物またはその塩類
JPS59101448A (ja) *	1982-11-30	1984-06-12	Eisai Co Ltd	ポリプレニルカルボン酸アミドおよびその製造方法ならびにそれを含有する医薬
JPS59152354A (ja) *	1983-02-21	1984-08-31	Nisshin Flour Milling Co Ltd	イソプレニル酸アミド誘導体
JPS6122054A (ja) *	1984-05-09	1986-01-30	Eisai Co Ltd	ポリプレニル系化合物
AU604660B2 (en) *	1985-12-17	1991-01-03	Wellcome Foundation Limited, The	Pesticidal compounds
DE3913940A1 (de) *	1989-04-27	1990-10-31	Bayer Ag	N-formyl-n'-((meth)acryloyloxyalkyl)piperazin und n-formyl-n'-((meth)acryloylaminoalkyl)piperazin, adhaesivkomponenten zur behandlung kollagenhaltiger materialien, enthaltend diese verbindungen, sowie herstellung und anwendung dieser adhaesivkomponenten
US5254733A (en) *	1990-10-31	1993-10-19	Fujisawa Pharmaceutical Co., Ltd.	Process for producing an aliphatic amide and salts thereof
EP1158983A4 (fr) *	1999-03-03	2003-05-21	Merck & Co Inc	Inhibiteurs de prenyl-proteine transferases
EP2840077A1 (fr) *	2013-08-20	2015-02-25	DSM IP Assets B.V.	Processus de fabrication de nitriles hydrogénés
CN113453672B (zh) *	2019-02-21	2026-01-06	株式会社萩原农场生产研究所	癌细胞增殖抑制组合物和加工食品

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3147261A (en) *	1962-05-24	1964-09-01	Robert R Mod	Nu-acyl-nu'-methylpiperazines
US3621043A (en) *	1963-02-06	1971-11-16	Sumitomo Chemical Co	N-substituted octadecadienoic acid amides as cholesterol lowering agents
US3270033A (en) *	1963-02-25	1966-08-30	Evald L Skau	Nu-oleoylpyrrolidine
US3294794A (en) *	1963-12-19	1966-12-27	Raiford L Holmes	4-(2-alkenoyl, or 2 bromoalkanoyl) morpholines
US3404145A (en) *	1965-04-13	1968-10-01	Agriculture Usa	N-acyl derivatives of cyclic imines
GB1209903A (en) *	1966-09-15	1970-10-21	Zoecon Corp	Long chain hydrocarbon esters and acids and process for their production
CH508613A (de) *	1967-12-18	1971-06-15	Hoffmann La Roche	Verfahren zur Herstellung von Epoxyverbindungen
AU1648870A (en) *	1969-07-09	1971-12-23	Fmc Corporation	Method of controlling insects and compostion therefor
US3649590A (en) *	1969-09-02	1972-03-14	Zoecon Corp	Quaternary alkylated aliphatic amides
US3773805A (en) *	1971-05-03	1973-11-20	J Siddall	11-halo-3,7,11-trialkyl-2-alkenoic and 2,6-alkadienoic acid amides
JPS52131507A (en) *	1976-04-24	1977-11-04	Sankyo Co Ltd	Polyprenyl derivatives

1980
- 1980-08-04 US US06/175,213 patent/US4456603A/en not_active Expired - Lifetime
- 1980-08-04 PH PH24388A patent/PH16234A/en unknown
- 1980-08-07 CH CH598880A patent/CH644582A5/fr not_active IP Right Cessation
- 1980-08-11 AU AU61342/80A patent/AU531466B2/en not_active Ceased
- 1980-08-12 FR FR8017742A patent/FR2463122A1/fr active Granted
- 1980-08-12 DE DE19803030462 patent/DE3030462A1/de active Granted
- 1980-08-12 GB GB8026161A patent/GB2058782B/en not_active Expired
- 1980-08-13 ES ES494230A patent/ES494230A0/es active Granted
- 1980-08-13 SE SE8005712A patent/SE446977B/sv not_active IP Right Cessation
- 1980-08-14 IT IT24157/80A patent/IT1132406B/it active
- 1980-08-14 NL NL8004609A patent/NL8004609A/nl not_active Application Discontinuation
- 1980-08-14 CA CA000358233A patent/CA1148153A/fr not_active Expired
1981
- 1981-12-09 FR FR8122993A patent/FR2497802A1/fr active Granted
1984
- 1984-08-29 SE SE8404308A patent/SE8404308L/xx not_active Application Discontinuation
- 1984-12-04 US US06/677,893 patent/US4639450A/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
US4456603A (en)	1984-06-26
FR2463122A1 (fr)	1981-02-20
IT1132406B (it)	1986-07-02
DE3030462A1 (de)	1981-03-19
SE8404308D0 (sv)	1984-08-29
SE8005712L (sv)	1981-02-15
FR2497802A1 (fr)	1982-07-16
ES8106276A1 (es)	1981-08-01
FR2497802B1 (fr)	1985-01-18
CH644582A5 (fr)	1984-08-15
GB2058782A (en)	1981-04-15
AU531466B2 (en)	1983-08-25
SE8404308L (sv)	1984-08-29
ES494230A0 (es)	1981-08-01
AU6134280A (en)	1981-02-19
US4639450A (en)	1987-01-27
GB2058782B (en)	1983-06-08
CA1148153A (fr)	1983-06-14
PH16234A (en)	1983-08-11
DE3030462C2 (fr)	1989-10-05
IT8024157A0 (it)	1980-08-14
SE446977B (sv)	1986-10-20
FR2463122B1 (fr)	1983-06-17

Legal Events

Date	Code	Title
1985-01-01	A85	Still pending on 85-01-01
1987-10-01	BA	A request for search or an international-type search has been filed
1987-10-01	BB	A search report has been drawn up
1988-02-01	BC	A request for examination has been filed
1991-04-02	BV	The patent application has lapsed

Publication	Publication Date	Title
NL8004609A (nl)	1981-02-17	Carbonzuuramiden en farmaceutisch preparaat alsmede werkwijze voor het bereiden daarvan.
US3398151A (en)	1968-08-20	Azaspirodecanediones and azaspiroundecanediones
AU726310B2 (en)	2000-11-02	N-aminoalkyldibenzofurancarboxamides as dopamine receptor subtype specific ligands
CA2279620C (fr)	2008-07-15	Ligands de 1-phenyle-4-benzylpiperazines specifiques pour le sous-type du recepteur de dopamine (d4)
CZ398191A3 (en)	1993-02-17	Novel 4-amino alkyl-2(3h)-indolones and pharmaceutical compositions containing them
ES2036926A1 (es)	1993-06-01	"procedimiento para la obtencion de derivados de la (2-alquil-3-piridil)metilpiperazina".
SE8405754D0 (sv)	1984-11-16	7-karboximetoxi-furo-(3,4-c)-pyridinderivat, framstellning derav och terapeutiska kompositioner innehallande dem
WO1990012574A1 (fr)	1990-11-01	Composes agonistes de la dopamine
IE53520B1 (en)	1988-12-07	N-(4,5-dihydrothiazol-2-yl)-3-quinoline carboxamide derivatives
EP0136274A1 (fr)	1985-04-03	Dérivés de 1-pipérazinecarboxamide, procédé de leur préparation et leur utilisation dans des compositions pharmaceutiques
CA2251989A1 (fr)	1997-10-30	Aminoalkylcarboxamides tricycliques, nouveaux ligands specifiques a des sous-types de recepteurs de la dopamine d3
NZ238438A (en)	1992-09-25	N-(4-(trifluoromethylpyridin-2-yl)piperazinylalkyl)benzamide derivatives with improved preferential serotonin-1a binding activity; pharmaceutical compositions and preparatory processes
GB1569251A (en)	1980-06-11	Pyridobenzodiazepines
NL8001981A (nl)	1980-10-07	Benzoxepinederivaat en farmaceutische preparaten op basis daarvan.
JPH05500958A (ja)	1993-02-25	神経保護剤用イミノメタノジベンゾ（ａ，ｄ）シクロヘプテン誘導体
EP0010896B1 (fr)	1981-12-30	Composés organiques diaminés utilisables comme substances actives hypoglycémiques administrables par voie orale et compositions pharmaceutiques les contenant
US3465080A (en)	1969-09-02	Therapeutic compositions containing morpholinoalkylene - indoles and methods of administering such in the treatment of depression
US4009271A (en)	1977-02-22	6-aza-3h-1,4-benzodiazepines
Ryder et al.	1999	Structure-activity relationship at the proximal phenyl group in a series of non-peptidyl N-type calcium channel antagonists
WO1997034884A1 (fr)	1997-09-25	Nouveaux n-aminoalkyl-2-anthracenecarboxamides; nouveaux ligands specifiques de sous-type de recepteur de dopamine
US6743796B2 (en)	2004-06-01	Piperazinyl-isatins
US5827847A (en)	1998-10-27	Treatment of cognitive disorders with piperazine derivatives
GB1591120A (en)	1981-06-17	Derivatives of a-amino benzimidazole-5-propanoic acid their preparation and compositions containing them
US3505452A (en)	1970-04-07	Methods of inhibiting gastric secretion with benzo(c)phenothiazines
Thomas et al.	2008	Reaction of α-(n-Alkylcarbonyloxy) alkyl (ACOA) Halides with 4-Hydroxyacetanilide and 2, 2, 5, 7, 8-Pentamethyl-6-chromanol: The Effect of Steric Hindrance on Reaction Path