NO784394L - Fremgangsmaate ved fremstilling av aminofenyl-etherforbindelser - Google Patents

Fremgangsmaate ved fremstilling av aminofenyl-etherforbindelser

Info

Publication number: NO784394L
Authority: NO; Norway
Prior art keywords: group; lower alkyl; denotes; substituted; formula
Prior art date: 1977-12-29

Application number

NO784394A

Other languages

English (en)

Norwegian (no)

Inventor

Jun Matsumoto

Tadao Kojima

Isao Ohata

Noboru Sato

Original Assignee

Yamanouchi Pharma 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.)

1977-12-29

Filing date

1978-12-28

Publication date

1979-07-02

1977-12-29 Priority claimed from JP15809977A external-priority patent/JPS5492926A/ja

1978-03-25 Priority claimed from JP3462478A external-priority patent/JPS54128535A/ja

1978-07-26 Priority claimed from JP9129278A external-priority patent/JPS5519217A/ja

1978-12-28 Application filed by Yamanouchi Pharma Co Ltd filed Critical Yamanouchi Pharma Co Ltd

1979-07-02 Publication of NO784394L publication Critical patent/NO784394L/no

Links

238000000034 method Methods 0.000 title claims description 39
238000002360 preparation method Methods 0.000 title claims description 3
GOJFAKBEASOYNM-UHFFFAOYSA-N 2-(2-aminophenoxy)aniline Chemical class NC1=CC=CC=C1OC1=CC=CC=C1N GOJFAKBEASOYNM-UHFFFAOYSA-N 0.000 title description 4
229910052757 nitrogen Inorganic materials 0.000 claims description 135
150000001875 compounds Chemical class 0.000 claims description 80
-1 aminophenyl ether compound Chemical class 0.000 claims description 75
125000000217 alkyl group Chemical group 0.000 claims description 63
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 25
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 22
125000004432 carbon atom Chemical group C* 0.000 claims description 21
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
125000003118 aryl group Chemical group 0.000 claims description 10
125000003277 amino group Chemical group 0.000 claims description 8
125000003710 aryl alkyl group Chemical group 0.000 claims description 8
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
229910052799 carbon Inorganic materials 0.000 claims description 7
125000005843 halogen group Chemical group 0.000 claims description 7
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 6
238000004519 manufacturing process Methods 0.000 claims description 6
125000000623 heterocyclic group Chemical group 0.000 claims description 5
150000003839 salts Chemical class 0.000 claims description 5
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 2
125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
125000003386 piperidinyl group Chemical group 0.000 claims description 2
125000001183 hydrocarbyl group Chemical group 0.000 claims 3
125000004429 atom Chemical group 0.000 claims 1
229910052739 hydrogen Inorganic materials 0.000 description 146
238000000921 elemental analysis Methods 0.000 description 69
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 60
238000002844 melting Methods 0.000 description 60
230000008018 melting Effects 0.000 description 60
239000000203 mixture Substances 0.000 description 54
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 52
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 45
239000000243 solution Substances 0.000 description 42
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 39
239000007858 starting material Substances 0.000 description 37
239000000047 product Substances 0.000 description 34
239000002904 solvent Substances 0.000 description 34
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical compound CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 description 32
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 32
HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 32
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 30
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 30
239000013078 crystal Substances 0.000 description 29
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 27
238000001816 cooling Methods 0.000 description 22
239000011541 reaction mixture Substances 0.000 description 19
238000003756 stirring Methods 0.000 description 18
229960001413 acetanilide Drugs 0.000 description 17
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 16
235000012000 cholesterol Nutrition 0.000 description 16
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 16
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 16
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
238000009835 boiling Methods 0.000 description 15
239000011780 sodium chloride Substances 0.000 description 13
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
102000015779 HDL Lipoproteins Human genes 0.000 description 12
108010010234 HDL Lipoproteins Proteins 0.000 description 12
238000006243 chemical reaction Methods 0.000 description 12
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
239000000741 silica gel Substances 0.000 description 11
229910002027 silica gel Inorganic materials 0.000 description 11
ARKJTWNPSFJACO-UHFFFAOYSA-N 4-[2-(4-methylcyclohexyl)propan-2-yloxy]aniline Chemical compound C1CC(C)CCC1C(C)(C)OC1=CC=C(N)C=C1 ARKJTWNPSFJACO-UHFFFAOYSA-N 0.000 description 10
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
230000000694 effects Effects 0.000 description 9
238000001914 filtration Methods 0.000 description 9
UODXCYZDMHPIJE-UHFFFAOYSA-N menthanol Chemical compound CC1CCC(C(C)(C)O)CC1 UODXCYZDMHPIJE-UHFFFAOYSA-N 0.000 description 9
238000010992 reflux Methods 0.000 description 9
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-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
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 8
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
229910000027 potassium carbonate Inorganic materials 0.000 description 8
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 7
239000001257 hydrogen Substances 0.000 description 7
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
239000000463 material Substances 0.000 description 6
UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
229920006395 saturated elastomer Polymers 0.000 description 6
206010003210 Arteriosclerosis Diseases 0.000 description 5
208000011775 arteriosclerosis disease Diseases 0.000 description 5
239000005457 ice water Substances 0.000 description 5
229910052740 iodine Inorganic materials 0.000 description 5
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 5
238000001953 recrystallisation Methods 0.000 description 5
239000000725 suspension Substances 0.000 description 5
DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 4
IBODDUNKEPPBKW-UHFFFAOYSA-N 1,5-dibromopentane Chemical compound BrCCCCCBr IBODDUNKEPPBKW-UHFFFAOYSA-N 0.000 description 4
HVXJILXIZHJUAE-UHFFFAOYSA-N 1-[4-[2-(4-methylcyclohexyl)propan-2-yloxy]phenyl]piperidine Chemical compound C1CC(C)CCC1C(C)(C)OC1=CC=C(N2CCCCC2)C=C1 HVXJILXIZHJUAE-UHFFFAOYSA-N 0.000 description 4
MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 4
KBNLYNNKZZJEGQ-SHTZXODSSA-N C(C)OC(=O)NC1=CC=C(C=C1)OC([C@@H]1CC[C@H](CC1)C)(C)C Chemical compound C(C)OC(=O)NC1=CC=C(C=C1)OC([C@@H]1CC[C@H](CC1)C)(C)C KBNLYNNKZZJEGQ-SHTZXODSSA-N 0.000 description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
150000001298 alcohols Chemical class 0.000 description 4
229910021529 ammonia Inorganic materials 0.000 description 4
150000001448 anilines Chemical class 0.000 description 4
150000001555 benzenes Chemical class 0.000 description 4
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 4
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 4
239000012280 lithium aluminium hydride Substances 0.000 description 4
239000003960 organic solvent Substances 0.000 description 4
238000006722 reduction reaction Methods 0.000 description 4
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
RIWRBSMFKVOJMN-UHFFFAOYSA-N 2-methyl-1-phenylpropan-2-ol Chemical compound CC(C)(O)CC1=CC=CC=C1 RIWRBSMFKVOJMN-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
IJXGDXZOHDXPKK-UHFFFAOYSA-N N-[4-[2-(4-methylcyclohexyl)propan-2-yloxy]phenyl]octadecanamide Chemical compound C1(CCC(CC1)C(C)(C)OC1=CC=C(NC(CCCCCCCCCCCCCCCCC)=O)C=C1)C IJXGDXZOHDXPKK-UHFFFAOYSA-N 0.000 description 3
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
ARKJTWNPSFJACO-JOCQHMNTSA-N [C@H]1(CC[C@H](CC1)C(C)(C)OC1=CC=C(N)C=C1)C Chemical compound [C@H]1(CC[C@H](CC1)C(C)(C)OC1=CC=C(N)C=C1)C ARKJTWNPSFJACO-JOCQHMNTSA-N 0.000 description 3
238000000862 absorption spectrum Methods 0.000 description 3
AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 3
239000008280 blood Substances 0.000 description 3
210000004369 blood Anatomy 0.000 description 3
150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
KNHUKKLJHYUCFP-UHFFFAOYSA-N clofibrate Chemical compound CCOC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 KNHUKKLJHYUCFP-UHFFFAOYSA-N 0.000 description 3
229960001214 clofibrate Drugs 0.000 description 3
VSSAZBXXNIABDN-UHFFFAOYSA-N cyclohexylmethanol Chemical compound OCC1CCCCC1 VSSAZBXXNIABDN-UHFFFAOYSA-N 0.000 description 3
KBNLYNNKZZJEGQ-UHFFFAOYSA-N ethyl N-[4-[2-(4-methylcyclohexyl)propan-2-yloxy]phenyl]carbamate Chemical compound C(C)OC(=O)NC1=CC=C(C=C1)OC(C1CCC(CC1)C)(C)C KBNLYNNKZZJEGQ-UHFFFAOYSA-N 0.000 description 3
238000000605 extraction Methods 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
229920000609 methyl cellulose Polymers 0.000 description 3
239000001923 methylcellulose Substances 0.000 description 3
235000010981 methylcellulose Nutrition 0.000 description 3
239000012046 mixed solvent Substances 0.000 description 3
230000000069 prophylactic effect Effects 0.000 description 3
239000012312 sodium hydride Substances 0.000 description 3
229910000104 sodium hydride Inorganic materials 0.000 description 3
238000001228 spectrum Methods 0.000 description 3
239000008096 xylene Substances 0.000 description 3
NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 description 2
DTSZTPPMUGNHKT-UHFFFAOYSA-N 1,5-dimethyl-2-propan-2-ylcyclohexan-1-ol Chemical compound CC(C)C1CCC(C)CC1(C)O DTSZTPPMUGNHKT-UHFFFAOYSA-N 0.000 description 2
VTBOTOBFGSVRMA-UHFFFAOYSA-N 1-Methylcyclohexanol Chemical compound CC1(O)CCCCC1 VTBOTOBFGSVRMA-UHFFFAOYSA-N 0.000 description 2
HNTGIJLWHDPAFN-UHFFFAOYSA-N 1-bromohexadecane Chemical compound CCCCCCCCCCCCCCCCBr HNTGIJLWHDPAFN-UHFFFAOYSA-N 0.000 description 2
JMSUNAQVHOHLMX-UHFFFAOYSA-N 1-cyclohexylethanol Chemical compound CC(O)C1CCCCC1 JMSUNAQVHOHLMX-UHFFFAOYSA-N 0.000 description 2
WFQDTOYDVUWQMS-UHFFFAOYSA-N 1-fluoro-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(F)C=C1 WFQDTOYDVUWQMS-UHFFFAOYSA-N 0.000 description 2
HMXMWOXFKFLOGK-UHFFFAOYSA-N 2-(4-methylcyclohexen-1-yl)propan-2-ol Chemical compound CC1CCC(C(C)(C)O)=CC1 HMXMWOXFKFLOGK-UHFFFAOYSA-N 0.000 description 2
SSZWOQANOUHNLV-UHFFFAOYSA-N 2-cyclohexylpropan-2-ol Chemical compound CC(C)(O)C1CCCCC1 SSZWOQANOUHNLV-UHFFFAOYSA-N 0.000 description 2
BDCFWIDZNLCTMF-UHFFFAOYSA-N 2-phenylpropan-2-ol Chemical compound CC(C)(O)C1=CC=CC=C1 BDCFWIDZNLCTMF-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 description 2
YIIMEMSDCNDGTB-UHFFFAOYSA-N Dimethylcarbamoyl chloride Chemical compound CN(C)C(Cl)=O YIIMEMSDCNDGTB-UHFFFAOYSA-N 0.000 description 2
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
102000007330 LDL Lipoproteins Human genes 0.000 description 2
108010007622 LDL Lipoproteins Proteins 0.000 description 2
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 2
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
NUYKNLHRSQRUFY-UHFFFAOYSA-N N-[4-[2-(4-methylcyclohexyl)propan-2-yloxy]phenyl]-3-phenylprop-2-enamide Chemical compound C(C=CC1=CC=CC=C1)(=O)NC1=CC=C(C=C1)OC(C1CCC(CC1)C)(C)C NUYKNLHRSQRUFY-UHFFFAOYSA-N 0.000 description 2
KDQZJDZJPLZMIZ-UHFFFAOYSA-N N-[4-[2-(4-methylcyclohexyl)propan-2-yloxy]phenyl]decanamide Chemical compound C1(CCC(CC1)C(C)(C)OC1=CC=C(NC(CCCCCCCCC)=O)C=C1)C KDQZJDZJPLZMIZ-UHFFFAOYSA-N 0.000 description 2
WXBWGYYMKYXORR-UHFFFAOYSA-N N-methyl-4-[2-(4-methylcyclohexyl)propan-2-yloxy]aniline Chemical compound C1(CCC(CC1)C(C)(C)OC1=CC=C(NC)C=C1)C WXBWGYYMKYXORR-UHFFFAOYSA-N 0.000 description 2
PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
239000002253 acid Substances 0.000 description 2
150000008065 acid anhydrides Chemical class 0.000 description 2
MIBQYWIOHFTKHD-UHFFFAOYSA-N adamantane-1-carbonyl chloride Chemical compound C1C(C2)CC3CC2CC1(C(=O)Cl)C3 MIBQYWIOHFTKHD-UHFFFAOYSA-N 0.000 description 2
239000003524 antilipemic agent Substances 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
238000010531 catalytic reduction reaction Methods 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
239000012141 concentrate Substances 0.000 description 2
RVOJTCZRIKWHDX-UHFFFAOYSA-N cyclohexanecarbonyl chloride Chemical compound ClC(=O)C1CCCCC1 RVOJTCZRIKWHDX-UHFFFAOYSA-N 0.000 description 2
HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 2
IPIVAXLHTVNRBS-UHFFFAOYSA-N decanoyl chloride Chemical compound CCCCCCCCCC(Cl)=O IPIVAXLHTVNRBS-UHFFFAOYSA-N 0.000 description 2
238000010908 decantation Methods 0.000 description 2
238000001035 drying Methods 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
238000009472 formulation Methods 0.000 description 2
239000008187 granular material Substances 0.000 description 2
150000002430 hydrocarbons Chemical group 0.000 description 2
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
239000008101 lactose Substances 0.000 description 2
150000002632 lipids Chemical class 0.000 description 2
238000001819 mass spectrum Methods 0.000 description 2
229940041616 menthol Drugs 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
239000002480 mineral oil Substances 0.000 description 2
235000010446 mineral oil Nutrition 0.000 description 2
GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
239000003208 petroleum Substances 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
238000000746 purification Methods 0.000 description 2
210000002966 serum Anatomy 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
229910000029 sodium carbonate Inorganic materials 0.000 description 2
239000000454 talc Substances 0.000 description 2
229910052623 talc Inorganic materials 0.000 description 2
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125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
239000000654 additive Substances 0.000 description 1
125000005910 alkyl carbonate group Chemical group 0.000 description 1
150000001350 alkyl halides Chemical class 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 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
208000010668 atopic eczema Diseases 0.000 description 1
SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
229940092714 benzenesulfonic acid Drugs 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
YTFJQDNGSQJFNA-UHFFFAOYSA-L benzyl phosphate Chemical compound [O-]P([O-])(=O)OCC1=CC=CC=C1 YTFJQDNGSQJFNA-UHFFFAOYSA-L 0.000 description 1
239000003613 bile acid Substances 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000004744 butyloxycarbonyl group Chemical group 0.000 description 1
CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
239000008116 calcium stearate Substances 0.000 description 1
235000013539 calcium stearate Nutrition 0.000 description 1
239000002775 capsule Substances 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
208000029078 coronary artery disease Diseases 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
DEFUSPNGFCCTEU-UHFFFAOYSA-N dicyclohexylmethanol Chemical compound C1CCCCC1C(O)C1CCCCC1 DEFUSPNGFCCTEU-UHFFFAOYSA-N 0.000 description 1
235000005911 diet Nutrition 0.000 description 1
230000037213 diet Effects 0.000 description 1
125000005883 dithianyl group Chemical group 0.000 description 1
239000003814 drug Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
ZUMNJDGBYXHASJ-UHFFFAOYSA-N ethyl 2-[5-[4-(3-methylsulfonylphenyl)phenyl]-3-(trifluoromethyl)pyrazol-1-yl]acetate Chemical compound CCOC(=O)CN1N=C(C(F)(F)F)C=C1C1=CC=C(C=2C=C(C=CC=2)S(C)(=O)=O)C=C1 ZUMNJDGBYXHASJ-UHFFFAOYSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
230000001747 exhibiting effect Effects 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
238000001640 fractional crystallisation Methods 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
235000011087 fumaric acid Nutrition 0.000 description 1
125000002541 furyl group Chemical group 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
ARBOVOVUTSQWSS-UHFFFAOYSA-N hexadecanoyl chloride Chemical compound CCCCCCCCCCCCCCCC(Cl)=O ARBOVOVUTSQWSS-UHFFFAOYSA-N 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
229930195733 hydrocarbon Natural products 0.000 description 1
230000000055 hyoplipidemic effect Effects 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
239000011630 iodine Substances 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
LSACYLWPPQLVSM-UHFFFAOYSA-N isobutyric acid anhydride Chemical compound CC(C)C(=O)OC(=O)C(C)C LSACYLWPPQLVSM-UHFFFAOYSA-N 0.000 description 1
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000004310 lactic acid Substances 0.000 description 1
235000014655 lactic acid Nutrition 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
229910000103 lithium hydride Inorganic materials 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
VJMRKWPMFQGIPI-UHFFFAOYSA-N n-(2-hydroxyethyl)-5-(hydroxymethyl)-3-methyl-1-[2-[[3-(trifluoromethyl)phenyl]methyl]-1-benzothiophen-7-yl]pyrazole-4-carboxamide Chemical compound OCC1=C(C(=O)NCCO)C(C)=NN1C1=CC=CC2=C1SC(CC=1C=C(C=CC=1)C(F)(F)F)=C2 VJMRKWPMFQGIPI-UHFFFAOYSA-N 0.000 description 1
BLIJXOOIHRSQRB-PXYINDEMSA-N n-[(2s)-1-[3-(3-chloro-4-cyanophenyl)pyrazol-1-yl]propan-2-yl]-5-(1-hydroxyethyl)-1h-pyrazole-3-carboxamide Chemical compound C([C@H](C)NC(=O)C=1NN=C(C=1)C(C)O)N(N=1)C=CC=1C1=CC=C(C#N)C(Cl)=C1 BLIJXOOIHRSQRB-PXYINDEMSA-N 0.000 description 1
GUOONOJYWQOJJP-DCMFLLSESA-N n-[(2s,3r)-3-hydroxy-1-phenyl-4-[[3-(trifluoromethoxy)phenyl]methylamino]butan-2-yl]-3-[methyl(methylsulfonyl)amino]-5-[(2r)-2-(4-methyl-1,3-thiazol-2-yl)pyrrolidine-1-carbonyl]benzamide Chemical compound C1([C@H]2CCCN2C(=O)C=2C=C(C=C(C=2)N(C)S(C)(=O)=O)C(=O)N[C@@H](CC=2C=CC=CC=2)[C@H](O)CNCC=2C=C(OC(F)(F)F)C=CC=2)=NC(C)=CS1 GUOONOJYWQOJJP-DCMFLLSESA-N 0.000 description 1
SKEAGJWUKCNICJ-LSDHHAIUSA-N n-[(4-fluoro-3-methoxyphenyl)methyl]-6-[2-[[(2s,5r)-5-(hydroxymethyl)-1,4-dioxan-2-yl]methyl]tetrazol-5-yl]-2-methylpyrimidine-4-carboxamide Chemical compound C1=C(F)C(OC)=CC(CNC(=O)C=2N=C(C)N=C(C=2)C2=NN(C[C@@H]3OC[C@@H](CO)OC3)N=N2)=C1 SKEAGJWUKCNICJ-LSDHHAIUSA-N 0.000 description 1
VZUGBLTVBZJZOE-KRWDZBQOSA-N n-[3-[(4s)-2-amino-1,4-dimethyl-6-oxo-5h-pyrimidin-4-yl]phenyl]-5-chloropyrimidine-2-carboxamide Chemical compound N1=C(N)N(C)C(=O)C[C@@]1(C)C1=CC=CC(NC(=O)C=2N=CC(Cl)=CN=2)=C1 VZUGBLTVBZJZOE-KRWDZBQOSA-N 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
229960003512 nicotinic acid Drugs 0.000 description 1
235000001968 nicotinic acid Nutrition 0.000 description 1
239000011664 nicotinic acid Substances 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
229930004008 p-menthane Natural products 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
230000002093 peripheral effect Effects 0.000 description 1
125000004344 phenylpropyl group Chemical group 0.000 description 1
239000006187 pill Substances 0.000 description 1
IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
229910000105 potassium hydride Inorganic materials 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
125000000714 pyrimidinyl group Chemical group 0.000 description 1
125000000168 pyrrolyl group Chemical group 0.000 description 1
150000003242 quaternary ammonium salts Chemical class 0.000 description 1
230000001603 reducing effect Effects 0.000 description 1
OEBIHOVSAMBXIB-SJKOYZFVSA-N selitrectinib Chemical compound C[C@@H]1CCC2=NC=C(F)C=C2[C@H]2CCCN2C2=NC3=C(C=NN3C=C2)C(=O)N1 OEBIHOVSAMBXIB-SJKOYZFVSA-N 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
238000013222 sprague-dawley male rat Methods 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
125000005504 styryl group Chemical group 0.000 description 1
239000003826 tablet Substances 0.000 description 1
125000001113 thiadiazolyl group Chemical group 0.000 description 1
125000000335 thiazolyl group Chemical group 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
229910052718 tin Inorganic materials 0.000 description 1
239000011135 tin Substances 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
CFJYNSNXFXLKNS-UHFFFAOYSA-N trans-p-menthane Natural products CC(C)C1CCC(C)CC1 CFJYNSNXFXLKNS-UHFFFAOYSA-N 0.000 description 1
150000003626 triacylglycerols Chemical class 0.000 description 1
UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000011701 zinc Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
- C07D213/82—Amides; Imides in position 3
- 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
- C07D295/04—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/096—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Hydrogenated Pyridines (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

NO784394A 1977-12-29 1978-12-28 Fremgangsmaate ved fremstilling av aminofenyl-etherforbindelser NO784394L (no)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
JP15809977A JPS5492926A (en)	1977-12-29	1977-12-29	Compound of aminophenyl ether and its preparation
JP3462478A JPS54128535A (en)	1978-03-25	1978-03-25	Aminophenyl ether compound and its preparation
JP9129278A JPS5519217A (en)	1978-07-26	1978-07-26	Aminophenyl ether derivative and its preparation

Publications (1)

Publication Number	Publication Date
NO784394L true NO784394L (no)	1979-07-02

Family

ID=27288474

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
NO784394A NO784394L (no)	1977-12-29	1978-12-28	Fremgangsmaate ved fremstilling av aminofenyl-etherforbindelser
NO820355A NO820355L (no)	1977-12-29	1982-02-05	Fremgangsmaate ved fremstilling av cykliske aminofenyletherforbindelser.

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
NO820355A NO820355L (no)	1977-12-29	1982-02-05	Fremgangsmaate ved fremstilling av cykliske aminofenyletherforbindelser.

Country Status (12)

Country	Link
AT (1)	AT367738B (de)
AU (1)	AU4301778A (de)
CA (1)	CA1110248A (de)
DE (1)	DE2854595A1 (de)
DK (1)	DK584978A (de)
ES (3)	ES476458A1 (de)
FR (1)	FR2413382A1 (de)
GB (1)	GB2011888B (de)
IT (1)	IT7869973A0 (de)
NL (1)	NL7812574A (de)
NO (2)	NO784394L (de)
SE (1)	SE7813355L (de)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4261651A (en) *	1978-05-31	1981-04-14	The Secretary Of State For Defence In Her Britannic Majesty's Government Of The United Kingdom Of Great Britain And Northern Ireland	Liquid crystal compounds
DE2948056A1 (de) *	1979-11-29	1981-06-04	Boehringer Mannheim Gmbh, 6800 Mannheim	Neue aminopropanolderivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel
US5527945A (en) *	1989-02-10	1996-06-18	Basf Aktiengesellschaft	Diphenylheteroalkyl derivatives, the preparation thereof and drugs and cosmetics prepared therefrom
DE3903989A1 (de) *	1989-02-10	1990-09-20	Basf Ag	Diphenylheteroalkylderivate, ihre herstellung und daraus hergestellte arzneimittel und kosmetika

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US1793030A (en) *	1930-03-01	1931-02-17	Thorp Lambert	Isopropyl ether of para-acetyl amino phenol
GB1093121A (en) *	1963-05-31	1967-11-29	Wellcome Found	Etherified ªÐ-hydroxyanilines

1978
- 1978-12-15 GB GB7848658A patent/GB2011888B/en not_active Expired
- 1978-12-18 DE DE19782854595 patent/DE2854595A1/de not_active Ceased
- 1978-12-18 CA CA318,098A patent/CA1110248A/en not_active Expired
- 1978-12-22 FR FR7836263A patent/FR2413382A1/fr not_active Withdrawn
- 1978-12-27 NL NL7812574A patent/NL7812574A/xx not_active Application Discontinuation
- 1978-12-28 DK DK584978A patent/DK584978A/da unknown
- 1978-12-28 IT IT7869973A patent/IT7869973A0/it unknown
- 1978-12-28 SE SE7813355A patent/SE7813355L/xx unknown
- 1978-12-28 ES ES476458A patent/ES476458A1/es not_active Expired
- 1978-12-28 NO NO784394A patent/NO784394L/no unknown
- 1978-12-29 AT AT0935778A patent/AT367738B/de not_active IP Right Cessation
- 1978-12-29 AU AU43017/78A patent/AU4301778A/en active Pending
1979
- 1979-06-12 ES ES481505A patent/ES481505A1/es not_active Expired
- 1979-06-12 ES ES481504A patent/ES481504A1/es not_active Expired
1982
- 1982-02-05 NO NO820355A patent/NO820355L/no unknown

Also Published As

Publication number	Publication date
FR2413382A1 (fr)	1979-07-27
DK584978A (da)	1979-06-30
SE7813355L (sv)	1979-06-30
ES481505A1 (es)	1980-04-01
ATA935778A (de)	1981-12-15
DE2854595A1 (de)	1979-07-12
ES481504A1 (es)	1980-04-01
GB2011888A (en)	1979-07-18
ES476458A1 (es)	1979-11-16
GB2011888B (en)	1982-09-22
CA1110248A (en)	1981-10-06
IT7869973A0 (it)	1978-12-28
AU4301778A (en)	1979-07-05
NL7812574A (nl)	1979-07-03
AT367738B (de)	1982-07-26
NO820355L (no)	1979-07-02

Publication	Publication Date	Title
US3900481A (en)	1975-08-19	Derivatives of pyrrolidine and piperidine
AU2006242950B2 (en)	2013-01-10	Phenoxypropylpiperidines and -pyrrolidines and their use as histamine H3 -receptor ligands
EP0429685A1 (de)	1991-06-05	Oxoindolderivate
US3634410A (en)	1972-01-11	Amides of benzoic acids with amine substituted piperidines
DE19933926A1 (de)	2001-01-25	Biphenylderivate, ihre Herstellung und ihre Verwendung als Arzneimittel
EP0024382A1 (de)	1981-03-04	Piperidinderivate, ihre Herstellung und sie enthaltende pharmazeutische Zusammensetzungen
JPH075539B2 (ja)	1995-01-25	置換スルホンアミドベンズアミド及びその製法
KR900001204B1 (ko)	1990-02-28	1-[(아미노알킬 및 아미노알킬아미노)카보닐 및 티오카보닐]-α, α-디아릴피롤리딘, 피페리딘 및 호모피페리딘 아세트아미드 및 아세토니트릴의 제조방법
US4460607A (en)	1984-07-17	Lipid absorption-inhibiting agents and their use
US4207327A (en)	1980-06-10	N-(4-Pyrazolidinyl)benzamides and their amino precursors
JPH0283375A (ja)	1990-03-23	２−置換ピペラジニル−２−（１，２−ベンズイソキサゾール−３−イル）酢酸誘導体
US4457931A (en)	1984-07-03	Piperazine derivatives with anticholinergic and/or antihistaminic activity
EP0333315B1 (de)	1991-06-12	Azacyclische Verbindungen, Verfahren zu ihrer Herstellung und ihre Verwendung als pharmazeutisches Mittel
US4210660A (en)	1980-07-01	Benzamide derivatives
US4021552A (en)	1977-05-03	10-[ω-(BENZOYLPIPERIDINYL)ALKYL]PHENOTHIAZINES
NO784394L (no)	1979-07-02	Fremgangsmaate ved fremstilling av aminofenyl-etherforbindelser
US4044147A (en)	1977-08-23	N-(acyl)-p-amino-N'-(monosubstituted)-benzamide anti-ulcer agents
KR900005133B1 (ko)	1990-07-20	아릴옥시-n-(아미노알킬)-1-피롤리딘 및 피페리딘 카복스아미드 및 카보티오아미드의 제조방법, 및 이를 함유하는 약제조성물
US4442102A (en)	1984-04-10	1,5-Diphenylpyrazolin-3-one compounds, process and intermediates for preparation thereof and pharmaceutical compositions containing same
US4005209A (en)	1977-01-25	Antiarrhythmic method utilizing fluoroalkoxy-N-piperidyl and pyridyl benzamides
CA1090366A (en)	1980-11-25	N-substituted aralkylanilines having hypolipidaemic activity
US3562276A (en)	1971-02-09	Diarylcyclopropane piperazides possessing enhanced antihistaminic,antiserotoninic and antiexudative activity
EP0449195A2 (de)	1991-10-02	Aminobenzolverbindungen, Herstellung und Verwendung
US4096331A (en)	1978-06-20	1-Substituted-3-aminoethoxypyrrolidines
SK279199B6 (sk)	1998-07-08	Diamidy n,n'-bis-/alkoxyalkyl/-pyridín-2,4-dikarbo