CA1050985A - Substituted-phenyl substituted-alkyl ethers and the preparation thereof - Google Patents

Substituted-phenyl substituted-alkyl ethers and the preparation thereof

Info

Publication number: CA1050985A
Authority: CA; Canada
Prior art keywords: hydrogen; methyl; alkyl; process according; phenyl
Prior art date: 1974-06-04
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.): Expired

Application number

CA228,557A

Other languages

English (en)

French (fr)

Other versions

CA228557S (en

Inventor

Takashi Kamiya

Yoshihisa Saito

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Fujisawa Pharmaceutical Co Ltd

Original Assignee

Fujisawa Pharmaceutical 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.)

1974-06-04

Filing date

1975-06-04

Publication date

1979-03-20

1974-06-04 Priority claimed from JP49063658A external-priority patent/JPS593465B2/ja

1974-06-10 Priority claimed from JP6627574A external-priority patent/JPS50157326A/ja

1974-06-10 Priority claimed from JP6627474A external-priority patent/JPS593466B2/ja

1975-02-05 Priority claimed from JP1577575A external-priority patent/JPS5929575B2/ja

1975-02-06 Priority claimed from JP50015938A external-priority patent/JPS5929576B2/ja

1975-03-03 Priority claimed from JP2632775A external-priority patent/JPS5929577B2/ja

1975-03-04 Priority claimed from JP2679675A external-priority patent/JPS5929578B2/ja

1975-03-06 Priority claimed from JP2787075A external-priority patent/JPS5929579B2/ja

1975-03-06 Priority claimed from JP2786975A external-priority patent/JPS6025425B2/ja

1975-03-08 Priority claimed from JP2837675A external-priority patent/JPS5929580B2/ja

1975-06-04 Application filed by Fujisawa Pharmaceutical Co Ltd filed Critical Fujisawa Pharmaceutical Co Ltd

1979-03-20 Publication of CA1050985A publication Critical patent/CA1050985A/en

1979-03-20 Application granted granted Critical

Status Expired legal-status Critical Current

Links

238000002360 preparation method Methods 0.000 title description 4
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 216
239000001257 hydrogen Substances 0.000 claims abstract description 215
238000000034 method Methods 0.000 claims abstract description 181
150000001875 compounds Chemical class 0.000 claims abstract description 139
150000002431 hydrogen Chemical group 0.000 claims abstract description 92
150000003839 salts Chemical class 0.000 claims abstract description 83
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 60
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 55
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 48
229910052736 halogen Inorganic materials 0.000 claims abstract description 45
150000002367 halogens Chemical group 0.000 claims abstract description 43
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 29
125000003545 alkoxy group Chemical group 0.000 claims abstract description 24
125000002947 alkylene group Chemical group 0.000 claims abstract description 13
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims abstract description 8
-1 benzyl pyridyl Chemical group 0.000 claims description 158
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 99
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 95
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 82
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 80
238000006243 chemical reaction Methods 0.000 claims description 74
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 68
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 68
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 64
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 54
229910052757 nitrogen Inorganic materials 0.000 claims description 43
125000006705 (C5-C7) cycloalkyl group Chemical group 0.000 claims description 42
125000004433 nitrogen atom Chemical group N* 0.000 claims description 39
239000002253 acid Substances 0.000 claims description 30
125000000719 pyrrolidinyl group Chemical group 0.000 claims description 24
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 20
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 14
125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 12
125000004076 pyridyl group Chemical group 0.000 claims description 11
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 10
125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 9
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 8
235000019260 propionic acid Nutrition 0.000 claims description 7
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 7
ZEYJNGVEPKXOHX-UHFFFAOYSA-N 2-[4-[(4-chloroanilino)methyl]phenoxy]propanoic acid Chemical compound C1=CC(OC(C)C(O)=O)=CC=C1CNC1=CC=C(Cl)C=C1 ZEYJNGVEPKXOHX-UHFFFAOYSA-N 0.000 claims description 5
YGDGMNSYGZMTEI-UHFFFAOYSA-N ethyl 2-[4-[(4-chloroanilino)methyl]phenoxy]-2-methylpropanoate Chemical compound C1=CC(OC(C)(C)C(=O)OCC)=CC=C1CNC1=CC=C(Cl)C=C1 YGDGMNSYGZMTEI-UHFFFAOYSA-N 0.000 claims description 5
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
125000005843 halogen group Chemical group 0.000 claims description 4
230000020335 dealkylation Effects 0.000 claims description 3
238000006900 dealkylation reaction Methods 0.000 claims description 3
230000032050 esterification Effects 0.000 claims description 3
238000005886 esterification reaction Methods 0.000 claims description 3
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 32
239000000126 substance Substances 0.000 claims 17
238000004519 manufacturing process Methods 0.000 claims 9
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 9
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 8
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 8
125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims 7
125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 5
125000001309 chloro group Chemical group Cl* 0.000 claims 5
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 4
125000001246 bromo group Chemical group Br* 0.000 claims 4
125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims 1
101100006371 Arabidopsis thaliana CHX3 gene Proteins 0.000 claims 1
125000001442 methylidyne group Chemical group [H]C#[*] 0.000 claims 1
125000000547 substituted alkyl group Chemical group 0.000 claims 1
125000000217 alkyl group Chemical group 0.000 abstract description 113
125000003118 aryl group Chemical group 0.000 abstract description 46
125000000623 heterocyclic group Chemical group 0.000 abstract description 18
150000002170 ethers Chemical class 0.000 abstract description 5
230000000055 hyoplipidemic effect Effects 0.000 abstract description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 184
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 175
239000000203 mixture Substances 0.000 description 95
239000000243 solution Substances 0.000 description 91
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 90
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 79
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 72
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 54
239000002904 solvent Substances 0.000 description 54
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 48
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 45
239000000284 extract Substances 0.000 description 42
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 40
239000007864 aqueous solution Substances 0.000 description 38
150000002148 esters Chemical class 0.000 description 38
239000000047 product Substances 0.000 description 35
238000003756 stirring Methods 0.000 description 33
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 32
239000013078 crystal Substances 0.000 description 30
230000002829 reductive effect Effects 0.000 description 30
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 27
239000007788 liquid Substances 0.000 description 26
239000011541 reaction mixture Substances 0.000 description 26
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 24
238000000862 absorption spectrum Methods 0.000 description 24
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 23
238000001816 cooling Methods 0.000 description 23
238000001914 filtration Methods 0.000 description 22
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 22
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 20
125000004432 carbon atom Chemical group C* 0.000 description 19
238000010438 heat treatment Methods 0.000 description 19
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 18
239000002585 base Substances 0.000 description 18
239000003921 oil Substances 0.000 description 18
235000019198 oils Nutrition 0.000 description 18
239000011734 sodium Substances 0.000 description 17
229910052708 sodium Inorganic materials 0.000 description 17
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical class 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 16
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 16
229910052943 magnesium sulfate Inorganic materials 0.000 description 16
235000019341 magnesium sulphate 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
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 14
229910052783 alkali metal Inorganic materials 0.000 description 14
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 13
238000001035 drying Methods 0.000 description 13
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 12
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 12
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 12
239000003054 catalyst Substances 0.000 description 12
229910002027 silica gel Inorganic materials 0.000 description 12
239000000741 silica gel Substances 0.000 description 12
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 11
125000004005 formimidoyl group Chemical group [H]\N=C(/[H])* 0.000 description 11
238000006722 reduction reaction Methods 0.000 description 11
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
229910052799 carbon Inorganic materials 0.000 description 10
238000004440 column chromatography Methods 0.000 description 10
239000000706 filtrate Substances 0.000 description 10
229920006395 saturated elastomer Polymers 0.000 description 10
239000012279 sodium borohydride Substances 0.000 description 10
229910000033 sodium borohydride Inorganic materials 0.000 description 10
239000000725 suspension Substances 0.000 description 10
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 9
IOLQWGVDEFWYNP-UHFFFAOYSA-N ethyl 2-bromo-2-methylpropanoate Chemical compound CCOC(=O)C(C)(C)Br IOLQWGVDEFWYNP-UHFFFAOYSA-N 0.000 description 9
229910052697 platinum Inorganic materials 0.000 description 9
239000007858 starting material Substances 0.000 description 9
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
241000786363 Rhampholeon spectrum Species 0.000 description 8
125000001931 aliphatic group Chemical group 0.000 description 8
150000001721 carbon Chemical group 0.000 description 8
229910000027 potassium carbonate Inorganic materials 0.000 description 8
235000011181 potassium carbonates Nutrition 0.000 description 8
229910052784 alkaline earth metal Inorganic materials 0.000 description 7
239000003795 chemical substances by application Substances 0.000 description 7
125000001424 substituent group Chemical group 0.000 description 7
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 6
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 6
150000001408 amides Chemical class 0.000 description 6
238000007796 conventional method Methods 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 6
229910052751 metal Inorganic materials 0.000 description 6
239000002184 metal Substances 0.000 description 6
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
150000007530 organic bases Chemical class 0.000 description 6
229910052763 palladium Inorganic materials 0.000 description 6
238000001953 recrystallisation Methods 0.000 description 6
229910000030 sodium bicarbonate Inorganic materials 0.000 description 6
235000017557 sodium bicarbonate Nutrition 0.000 description 6
239000012312 sodium hydride Substances 0.000 description 6
229910000104 sodium hydride Inorganic materials 0.000 description 6
229910052717 sulfur Inorganic materials 0.000 description 6
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 5
239000000084 colloidal system Substances 0.000 description 5
150000007529 inorganic bases Chemical class 0.000 description 5
125000004430 oxygen atom Chemical group O* 0.000 description 5
229910000029 sodium carbonate Inorganic materials 0.000 description 5
239000011780 sodium chloride Substances 0.000 description 5
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 5
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 4
GRFNBEZIAWKNCO-UHFFFAOYSA-N 3-pyridinol Chemical compound OC1=CC=CN=C1 GRFNBEZIAWKNCO-UHFFFAOYSA-N 0.000 description 4
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 4
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 4
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
150000008065 acid anhydrides Chemical class 0.000 description 4
150000001340 alkali metals Chemical class 0.000 description 4
AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 4
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
238000004458 analytical method Methods 0.000 description 4
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
229910052794 bromium Inorganic materials 0.000 description 4
238000010531 catalytic reduction reaction Methods 0.000 description 4
239000000460 chlorine Substances 0.000 description 4
229910052801 chlorine Inorganic materials 0.000 description 4
238000004821 distillation Methods 0.000 description 4
239000003814 drug Substances 0.000 description 4
DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 4
FTPQUEAFAYVEMK-UHFFFAOYSA-N ethyl 2-[4-(bromomethyl)phenoxy]-2-methylpropanoate Chemical compound CCOC(=O)C(C)(C)OC1=CC=C(CBr)C=C1 FTPQUEAFAYVEMK-UHFFFAOYSA-N 0.000 description 4
229910052731 fluorine Inorganic materials 0.000 description 4
239000011737 fluorine Substances 0.000 description 4
238000006460 hydrolysis reaction Methods 0.000 description 4
229910052740 iodine Inorganic materials 0.000 description 4
239000012280 lithium aluminium hydride Substances 0.000 description 4
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
159000000000 sodium salts Chemical class 0.000 description 4
125000004434 sulfur atom Chemical group 0.000 description 4
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
229940086542 triethylamine Drugs 0.000 description 4
NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 3
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 3
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 3
CFXVSAYTPXCJNQ-UHFFFAOYSA-N 6-[(4-chloroanilino)methyl]-2,2-dimethyl-1,4-benzodioxin-3-one Chemical compound C1=C2OC(=O)C(C)(C)OC2=CC=C1CNC1=CC=C(Cl)C=C1 CFXVSAYTPXCJNQ-UHFFFAOYSA-N 0.000 description 3
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical class [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 3
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 3
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 3
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
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229910000288 alkali metal carbonate Inorganic materials 0.000 description 3
150000008041 alkali metal carbonates Chemical class 0.000 description 3
150000008051 alkyl sulfates Chemical class 0.000 description 3
125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 3
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SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 3
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239000012230 colorless oil Substances 0.000 description 3
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235000019253 formic acid Nutrition 0.000 description 3
230000007062 hydrolysis Effects 0.000 description 3
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
239000011630 iodine Substances 0.000 description 3
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150000002500 ions Chemical class 0.000 description 3
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229910052700 potassium Inorganic materials 0.000 description 3
239000011591 potassium Substances 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
229940124597 therapeutic agent Drugs 0.000 description 3
230000001225 therapeutic effect Effects 0.000 description 3
125000005270 trialkylamine group Chemical group 0.000 description 3
238000010792 warming Methods 0.000 description 3
OGNVQLDIPUXYDH-ZPKKHLQPSA-N (2R,3R,4S)-3-(2-methylpropanoylamino)-4-(4-phenyltriazol-1-yl)-2-[(1R,2R)-1,2,3-trihydroxypropyl]-3,4-dihydro-2H-pyran-6-carboxylic acid Chemical compound CC(C)C(=O)N[C@H]1[C@H]([C@H](O)[C@H](O)CO)OC(C(O)=O)=C[C@@H]1N1N=NC(C=2C=CC=CC=2)=C1 OGNVQLDIPUXYDH-ZPKKHLQPSA-N 0.000 description 2
RXYPXQSKLGGKOL-UHFFFAOYSA-N 1,4-dimethylpiperazine Chemical compound CN1CCN(C)CC1 RXYPXQSKLGGKOL-UHFFFAOYSA-N 0.000 description 2
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 2
MVQVNTPHUGQQHK-UHFFFAOYSA-N 3-pyridinemethanol Chemical compound OCC1=CC=CN=C1 MVQVNTPHUGQQHK-UHFFFAOYSA-N 0.000 description 2
ZDEUJEHDUBUXNW-UHFFFAOYSA-N 4-[(4-chloroanilino)methyl]phenol Chemical compound C1=CC(O)=CC=C1CNC1=CC=C(Cl)C=C1 ZDEUJEHDUBUXNW-UHFFFAOYSA-N 0.000 description 2
QSNSCYSYFYORTR-UHFFFAOYSA-N 4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 description 2
XLSZMDLNRCVEIJ-UHFFFAOYSA-N 4-methylimidazole Chemical compound CC1=CNC=N1 XLSZMDLNRCVEIJ-UHFFFAOYSA-N 0.000 description 2
101150041968 CDC13 gene Proteins 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
241000282414 Homo sapiens Species 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 2
235000019502 Orange oil Nutrition 0.000 description 2
229920000388 Polyphosphate Polymers 0.000 description 2
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
239000007868 Raney catalyst Substances 0.000 description 2
229910000564 Raney nickel Inorganic materials 0.000 description 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-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
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
150000001335 aliphatic alkanes Chemical class 0.000 description 2
150000007933 aliphatic carboxylic acids Chemical class 0.000 description 2
229910000102 alkali metal hydride Inorganic materials 0.000 description 2
150000008046 alkali metal hydrides Chemical class 0.000 description 2
150000008044 alkali metal hydroxides Chemical class 0.000 description 2
150000001342 alkaline earth metals Chemical class 0.000 description 2
125000003282 alkyl amino group Chemical group 0.000 description 2
125000004414 alkyl thio group Chemical group 0.000 description 2
235000019270 ammonium chloride Nutrition 0.000 description 2
125000003435 aroyl group Chemical group 0.000 description 2
125000005110 aryl thio group Chemical group 0.000 description 2
125000004104 aryloxy group Chemical group 0.000 description 2
239000011230 binding agent Substances 0.000 description 2
ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 2
WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
DIKBFYAXUHHXCS-UHFFFAOYSA-N bromoform Chemical compound BrC(Br)Br DIKBFYAXUHHXCS-UHFFFAOYSA-N 0.000 description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
125000004744 butyloxycarbonyl group Chemical group 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
229910052804 chromium Inorganic materials 0.000 description 2
239000011651 chromium Substances 0.000 description 2
229910052802 copper Inorganic materials 0.000 description 2
239000010949 copper Substances 0.000 description 2
125000004093 cyano group Chemical group *C#N 0.000 description 2
125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 2
230000008034 disappearance Effects 0.000 description 2
239000003937 drug carrier Substances 0.000 description 2
229940093495 ethanethiol Drugs 0.000 description 2
VKFNUKHPPBQQSG-UHFFFAOYSA-N ethyl 2-[4-[(3-chlorophenyl)iminomethyl]phenoxy]-2-methylpropanoate Chemical compound C1=CC(OC(C)(C)C(=O)OCC)=CC=C1C=NC1=CC=CC(Cl)=C1 VKFNUKHPPBQQSG-UHFFFAOYSA-N 0.000 description 2
ODLGWIZDLFMOEU-UHFFFAOYSA-N ethyl 2-[4-[(4-chloroanilino)methyl]phenoxy]-2-methylbutanoate Chemical compound C1=CC(OC(C)(CC)C(=O)OCC)=CC=C1CNC1=CC=C(Cl)C=C1 ODLGWIZDLFMOEU-UHFFFAOYSA-N 0.000 description 2
FHZZSUAUZXWLRU-UHFFFAOYSA-N ethyl 2-[4-[(4-chloroanilino)methyl]phenoxy]-2-methylpropanoate;hydrochloride Chemical compound Cl.C1=CC(OC(C)(C)C(=O)OCC)=CC=C1CNC1=CC=C(Cl)C=C1 FHZZSUAUZXWLRU-UHFFFAOYSA-N 0.000 description 2
OXBIUAZWHYMGTN-UHFFFAOYSA-N ethyl 2-[4-[(benzylamino)methyl]phenoxy]-2-methylpropanoate;hydrochloride Chemical compound Cl.C1=CC(OC(C)(C)C(=O)OCC)=CC=C1CNCC1=CC=CC=C1 OXBIUAZWHYMGTN-UHFFFAOYSA-N 0.000 description 2
ARFLASKVLJTEJD-UHFFFAOYSA-N ethyl 2-bromopropanoate Chemical compound CCOC(=O)C(C)Br ARFLASKVLJTEJD-UHFFFAOYSA-N 0.000 description 2
FAOHUNAPIAABEG-UHFFFAOYSA-N ethyl 2-methyl-2-[4-[(2-methylpropylamino)methyl]phenoxy]propanoate;hydrochloride Chemical compound Cl.CCOC(=O)C(C)(C)OC1=CC=C(CNCC(C)C)C=C1 FAOHUNAPIAABEG-UHFFFAOYSA-N 0.000 description 2
RVFRPGLXTJLDOR-UHFFFAOYSA-N ethyl 2-methyl-2-[4-[(4-methylanilino)methyl]phenoxy]propanoate;hydrochloride Chemical compound Cl.C1=CC(OC(C)(C)C(=O)OCC)=CC=C1CNC1=CC=C(C)C=C1 RVFRPGLXTJLDOR-UHFFFAOYSA-N 0.000 description 2
FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 2
238000000605 extraction Methods 0.000 description 2
239000001530 fumaric acid Substances 0.000 description 2
LHGVFZTZFXWLCP-UHFFFAOYSA-N guaiacol Chemical compound COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 description 2
150000004820 halides Chemical class 0.000 description 2
125000005059 halophenyl group Chemical group 0.000 description 2
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 2
239000005457 ice water Substances 0.000 description 2
229910052741 iridium Inorganic materials 0.000 description 2
GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 2
ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
HSZCZNFXUDYRKD-UHFFFAOYSA-M lithium iodide Chemical compound [Li+].[I-] HSZCZNFXUDYRKD-UHFFFAOYSA-M 0.000 description 2
229910052749 magnesium Inorganic materials 0.000 description 2
239000011777 magnesium Substances 0.000 description 2
159000000003 magnesium salts Chemical class 0.000 description 2
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239000011976 maleic acid Substances 0.000 description 2
239000000463 material Substances 0.000 description 2
239000012452 mother liquor Substances 0.000 description 2
125000001624 naphthyl group Chemical group 0.000 description 2
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229910000480 nickel oxide Inorganic materials 0.000 description 2
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239000010502 orange oil Substances 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
GNRSAWUEBMWBQH-UHFFFAOYSA-N oxonickel Chemical compound [Ni]=O GNRSAWUEBMWBQH-UHFFFAOYSA-N 0.000 description 2
HBEQXAKJSGXAIQ-UHFFFAOYSA-N oxopalladium Chemical compound [Pd]=O HBEQXAKJSGXAIQ-UHFFFAOYSA-N 0.000 description 2
229910003445 palladium oxide Inorganic materials 0.000 description 2
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
239000001205 polyphosphate Substances 0.000 description 2
235000011176 polyphosphates Nutrition 0.000 description 2
235000015497 potassium bicarbonate Nutrition 0.000 description 2
229910000028 potassium bicarbonate Inorganic materials 0.000 description 2
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229910000105 potassium hydride Inorganic materials 0.000 description 2
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 2
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125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
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239000012264 purified product Substances 0.000 description 2
229910052703 rhodium Inorganic materials 0.000 description 2
239000010948 rhodium Substances 0.000 description 2
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238000010898 silica gel chromatography Methods 0.000 description 2
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241000894007 species Species 0.000 description 2
239000011593 sulfur Substances 0.000 description 2
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239000012000 urushibara nickel Substances 0.000 description 2
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239000011701 zinc Substances 0.000 description 2
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ANYMYIVRWMKBEJ-UHFFFAOYSA-N (1-oxidoquinolin-1-ium-2-yl)methanol Chemical compound C1=CC=CC2=[N+]([O-])C(CO)=CC=C21 ANYMYIVRWMKBEJ-UHFFFAOYSA-N 0.000 description 1
JFQJADVATLPJRF-IHWYPQMZSA-N (z)-3-bromobut-2-enoic acid Chemical compound C\C(Br)=C\C(O)=O JFQJADVATLPJRF-IHWYPQMZSA-N 0.000 description 1
125000006033 1,1-dimethyl-2-propenyl group Chemical group 0.000 description 1
YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 1
RUFUYGITBFQYSA-UHFFFAOYSA-N 1,8,9,10,10-pentachloro-9h-anthracene Chemical compound C1=CC(Cl)=C2C(Cl)C3=C(Cl)C=CC=C3C(Cl)(Cl)C2=C1 RUFUYGITBFQYSA-UHFFFAOYSA-N 0.000 description 1
DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
ORLCYMQZIPSODD-UHFFFAOYSA-N 1-chloro-2-[chloro(2,2,2-trichloroethoxy)phosphoryl]oxybenzene Chemical compound ClC1=CC=CC=C1OP(Cl)(=O)OCC(Cl)(Cl)Cl ORLCYMQZIPSODD-UHFFFAOYSA-N 0.000 description 1
AVFZOVWCLRSYKC-UHFFFAOYSA-N 1-methylpyrrolidine Chemical compound CN1CCCC1 AVFZOVWCLRSYKC-UHFFFAOYSA-N 0.000 description 1
QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 description 1
125000000453 2,2,2-trichloroethyl group Chemical group [H]C([H])(*)C(Cl)(Cl)Cl 0.000 description 1
125000001917 2,4-dinitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C(=C1*)[N+]([O-])=O)[N+]([O-])=O 0.000 description 1
LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
LWYLSIFFQWAXDO-UHFFFAOYSA-N 2-[4-[(4-chloro-n-methylanilino)methyl]phenoxy]-2-methylpropanoic acid Chemical compound C=1C=C(Cl)C=CC=1N(C)CC1=CC=C(OC(C)(C)C(O)=O)C=C1 LWYLSIFFQWAXDO-UHFFFAOYSA-N 0.000 description 1
ZVNLRFIXKURKHJ-UHFFFAOYSA-N 2-[4-[(4-chloroanilino)methyl]phenoxy]-2-methylbutanoic acid Chemical compound C1=CC(OC(C)(CC)C(O)=O)=CC=C1CNC1=CC=C(Cl)C=C1 ZVNLRFIXKURKHJ-UHFFFAOYSA-N 0.000 description 1
CCWMWXZSDMSBQT-UHFFFAOYSA-N 2-[4-[(4-chloroanilino)methyl]phenoxy]-2-methylpropan-1-ol Chemical compound C1=CC(OC(C)(CO)C)=CC=C1CNC1=CC=C(Cl)C=C1 CCWMWXZSDMSBQT-UHFFFAOYSA-N 0.000 description 1
ZCCDFDBNRCYYSY-UHFFFAOYSA-N 2-[4-[(4-chloroanilino)methyl]phenoxy]-2-methylpropanoic acid Chemical compound C1=CC(OC(C)(C)C(O)=O)=CC=C1CNC1=CC=C(Cl)C=C1 ZCCDFDBNRCYYSY-UHFFFAOYSA-N 0.000 description 1
UHGULLIUJBCTEF-UHFFFAOYSA-N 2-aminobenzothiazole Chemical compound C1=CC=C2SC(N)=NC2=C1 UHGULLIUJBCTEF-UHFFFAOYSA-N 0.000 description 1
ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 1
125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 1
AVZBOAGCVKEESJ-UHFFFAOYSA-O 2-ethyl-1,2-benzoxazol-2-ium-7-ol Chemical class C1=CC(O)=C2O[N+](CC)=CC2=C1 AVZBOAGCVKEESJ-UHFFFAOYSA-O 0.000 description 1
VYSRZETUSAOIMP-UHFFFAOYSA-N 2-furanacetic acid Chemical compound OC(=O)CC1=CC=CO1 VYSRZETUSAOIMP-UHFFFAOYSA-N 0.000 description 1
TZGPACAKMCUCKX-UHFFFAOYSA-N 2-hydroxyacetamide Chemical compound NC(=O)CO TZGPACAKMCUCKX-UHFFFAOYSA-N 0.000 description 1
CFMZSMGAMPBRBE-UHFFFAOYSA-N 2-hydroxyisoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(O)C(=O)C2=C1 CFMZSMGAMPBRBE-UHFFFAOYSA-N 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
WLJVXDMOQOGPHL-PPJXEINESA-N 2-phenylacetic acid Chemical compound O[14C](=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-PPJXEINESA-N 0.000 description 1
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239000001095 magnesium carbonate Substances 0.000 description 1
229910000021 magnesium carbonate Inorganic materials 0.000 description 1
VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
239000000347 magnesium hydroxide Substances 0.000 description 1
229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
239000000594 mannitol Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
229910001507 metal halide Inorganic materials 0.000 description 1
150000005309 metal halides Chemical class 0.000 description 1
229910000000 metal hydroxide Inorganic materials 0.000 description 1
150000004692 metal hydroxides Chemical class 0.000 description 1
NBTOZLQBSIZIKS-UHFFFAOYSA-N methoxide Chemical compound [O-]C NBTOZLQBSIZIKS-UHFFFAOYSA-N 0.000 description 1
HRDXJKGNWSUIBT-UHFFFAOYSA-N methoxybenzene Chemical group [CH2]OC1=CC=CC=C1 HRDXJKGNWSUIBT-UHFFFAOYSA-N 0.000 description 1
QRNDDJXJUHBGSG-UHFFFAOYSA-N methoxyethyne Chemical group COC#C QRNDDJXJUHBGSG-UHFFFAOYSA-N 0.000 description 1
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
CXHHBNMLPJOKQD-UHFFFAOYSA-M methyl carbonate Chemical compound COC([O-])=O CXHHBNMLPJOKQD-UHFFFAOYSA-M 0.000 description 1
CAAULPUQFIIOTL-UHFFFAOYSA-N methyl dihydrogen phosphate Chemical compound COP(O)(O)=O CAAULPUQFIIOTL-UHFFFAOYSA-N 0.000 description 1
229940017219 methyl propionate Drugs 0.000 description 1
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
125000004372 methylthioethyl group Chemical group [H]C([H])([H])SC([H])([H])C([H])([H])* 0.000 description 1
125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 description 1
125000004373 methylthiopropyl group Chemical group [H]C([H])([H])SC([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
239000002808 molecular sieve Substances 0.000 description 1
125000002950 monocyclic group Chemical group 0.000 description 1
CQDGTJPVBWZJAZ-UHFFFAOYSA-N monoethyl carbonate Chemical compound CCOC(O)=O CQDGTJPVBWZJAZ-UHFFFAOYSA-N 0.000 description 1
XDUOVFCMUNVFNQ-UHFFFAOYSA-N n,n-diethyl-3,3-dimethylbut-1-yn-1-amine Chemical compound CCN(CC)C#CC(C)(C)C XDUOVFCMUNVFNQ-UHFFFAOYSA-N 0.000 description 1
YDWDGEDMWCMBLI-UHFFFAOYSA-N n,n-diethylbut-1-yn-1-amine Chemical compound CCC#CN(CC)CC YDWDGEDMWCMBLI-UHFFFAOYSA-N 0.000 description 1
VMESOKCXSYNAKD-UHFFFAOYSA-N n,n-dimethylhydroxylamine Chemical compound CN(C)O VMESOKCXSYNAKD-UHFFFAOYSA-N 0.000 description 1
VOVZXURTCKPRDQ-CQSZACIVSA-N n-[4-[chloro(difluoro)methoxy]phenyl]-6-[(3r)-3-hydroxypyrrolidin-1-yl]-5-(1h-pyrazol-5-yl)pyridine-3-carboxamide Chemical compound C1[C@H](O)CCN1C1=NC=C(C(=O)NC=2C=CC(OC(F)(F)Cl)=CC=2)C=C1C1=CC=NN1 VOVZXURTCKPRDQ-CQSZACIVSA-N 0.000 description 1
UUIQMZJEGPQKFD-UHFFFAOYSA-N n-butyric acid methyl ester Natural products CCCC(=O)OC UUIQMZJEGPQKFD-UHFFFAOYSA-N 0.000 description 1
HZPNKQREYVVATQ-UHFFFAOYSA-L nickel(2+);diformate Chemical group [Ni+2].[O-]C=O.[O-]C=O HZPNKQREYVVATQ-UHFFFAOYSA-L 0.000 description 1
HKFZDVPCCOOGEV-UHFFFAOYSA-N nickel(3+);borate Chemical compound [Ni+3].[O-]B([O-])[O-] HKFZDVPCCOOGEV-UHFFFAOYSA-N 0.000 description 1
229910052755 nonmetal Inorganic materials 0.000 description 1
125000001715 oxadiazolyl group Chemical group 0.000 description 1
CELWCAITJAEQNL-UHFFFAOYSA-N oxan-2-ol Chemical compound OC1CCCCO1 CELWCAITJAEQNL-UHFFFAOYSA-N 0.000 description 1
125000002971 oxazolyl group Chemical group 0.000 description 1
150000002923 oximes Chemical class 0.000 description 1
MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229960003540 oxyquinoline Drugs 0.000 description 1
125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 description 1
125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
125000001148 pentyloxycarbonyl group Chemical group 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
125000006678 phenoxycarbonyl group Chemical group 0.000 description 1
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 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
150000003015 phosphoric acid halides Chemical class 0.000 description 1
UXCDUFKZSUBXGM-UHFFFAOYSA-N phosphoric tribromide Chemical compound BrP(Br)(Br)=O UXCDUFKZSUBXGM-UHFFFAOYSA-N 0.000 description 1
FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 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
229910003446 platinum oxide Inorganic materials 0.000 description 1
125000003367 polycyclic group Chemical group 0.000 description 1
229920000166 polytrimethylene carbonate Polymers 0.000 description 1
RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 description 1
229920001592 potato starch Polymers 0.000 description 1
YYFIGOPUHPDIBO-UHFFFAOYSA-N propanoic acid;hydrochloride Chemical compound Cl.CCC(O)=O YYFIGOPUHPDIBO-UHFFFAOYSA-N 0.000 description 1
125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
238000000746 purification Methods 0.000 description 1
125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
125000003373 pyrazinyl group Chemical group 0.000 description 1
125000003226 pyrazolyl group Chemical group 0.000 description 1
125000002098 pyridazinyl group Chemical group 0.000 description 1
150000003222 pyridines Chemical class 0.000 description 1
125000000714 pyrimidinyl group Chemical group 0.000 description 1
125000001422 pyrrolinyl group Chemical group 0.000 description 1
125000000168 pyrrolyl group Chemical group 0.000 description 1
MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
125000005493 quinolyl group Chemical group 0.000 description 1
239000011369 resultant mixture Substances 0.000 description 1
229910052895 riebeckite Inorganic materials 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
RBWSWDPRDBEWCR-RKJRWTFHSA-N sodium;(2r)-2-[(2r)-3,4-dihydroxy-5-oxo-2h-furan-2-yl]-2-hydroxyethanolate Chemical compound [Na+].[O-]C[C@@H](O)[C@H]1OC(=O)C(O)=C1O RBWSWDPRDBEWCR-RKJRWTFHSA-N 0.000 description 1
GIUSUAGSSNBIGT-UHFFFAOYSA-M sodium;2-[4-[(4-chloroanilino)methyl]-2-hydroxyphenoxy]-2-methylpropanoate Chemical compound [Na+].C1=C(O)C(OC(C)(C)C([O-])=O)=CC=C1CNC1=CC=C(Cl)C=C1 GIUSUAGSSNBIGT-UHFFFAOYSA-M 0.000 description 1
RZWQDAUIUBVCDD-UHFFFAOYSA-M sodium;benzenethiolate Chemical compound [Na+].[S-]C1=CC=CC=C1 RZWQDAUIUBVCDD-UHFFFAOYSA-M 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
DHCDFWKWKRSZHF-UHFFFAOYSA-N sulfurothioic S-acid Chemical compound OS(O)(=O)=S DHCDFWKWKRSZHF-UHFFFAOYSA-N 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
PUGUQINMNYINPK-UHFFFAOYSA-N tert-butyl 4-(2-chloroacetyl)piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCN(C(=O)CCl)CC1 PUGUQINMNYINPK-UHFFFAOYSA-N 0.000 description 1
125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
125000003831 tetrazolyl group Chemical group 0.000 description 1
125000001113 thiadiazolyl group Chemical group 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
125000005424 tosyloxy group Chemical group S(=O)(=O)(C1=CC=C(C)C=C1)O* 0.000 description 1
LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
229940035339 tri-chlor Drugs 0.000 description 1
125000001425 triazolyl group Chemical group 0.000 description 1
FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 description 1
125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
229940005605 valeric acid Drugs 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 1
229910052727 yttrium Inorganic materials 0.000 description 1
239000011592 zinc chloride Substances 0.000 description 1
235000005074 zinc chloride Nutrition 0.000 description 1
NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 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
- C07D213/72—Nitrogen atoms
- C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
- 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)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

CA228,557A 1974-06-04 1975-06-04 Substituted-phenyl substituted-alkyl ethers and the preparation thereof Expired CA1050985A (en)

Applications Claiming Priority (10)

Application Number	Priority Date	Filing Date	Title
JP49063658A JPS593465B2 (ja)	1974-06-04	1974-06-04	チカンアミノアルキルチカンフエノキシカルボンサンルイノセイゾウホウ
JP6627474A JPS593466B2 (ja)	1974-06-10	1974-06-10	チカンアルキルチカンフエノキシカルボンサンルイオセイゾウスルホウホウ
JP6627574A JPS50157326A (da)	1974-06-10	1974-06-10
JP1577575A JPS5929575B2 (ja)	1975-02-05	1975-02-05	置換フエノキシ脂肪酸類の製造法
JP50015938A JPS5929576B2 (ja)	1975-02-06	1975-02-06	置換フエノキシ脂肪酸エステル類の製造法
JP2632775A JPS5929577B2 (ja)	1975-03-03	1975-03-03	ジ置換アミノアルキル置換フエノキシ脂肪酸類の製造法
JP2679675A JPS5929578B2 (ja)	1975-03-04	1975-03-04	置換フエノキシ脂肪酸類を製造する方法
JP2787075A JPS5929579B2 (ja)	1975-03-06	1975-03-06	置換アルキル置換フエノキシカルボン酸類の製造法
JP2786975A JPS6025425B2 (ja)	1975-03-06	1975-03-06	置換フエノキシ脂肪酸類の合成法
JP2837675A JPS5929580B2 (ja)	1975-03-08	1975-03-08	置換アミノアルキル置換フエノキシ脂肪酸類の製造法

Publications (1)

Publication Number	Publication Date
CA1050985A true CA1050985A (en)	1979-03-20

Family

ID=27579658

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA228,557A Expired CA1050985A (en)	1974-06-04	1975-06-04	Substituted-phenyl substituted-alkyl ethers and the preparation thereof

Country Status (7)

Country	Link
AU (1)	AU8185575A (da)
CA (1)	CA1050985A (da)
CH (1)	CH613940A5 (da)
DE (1)	DE2524865A1 (da)
DK (1)	DK248875A (da)
FR (1)	FR2273518A1 (da)
GB (1)	GB1503953A (da)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AU2003245963B2 (en) *	2002-06-20	2008-06-26	Smithkline Beecham Corporation	Propionic acid derivatives and their use as hPPARs activators

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4214094A (en) *	1977-03-30	1980-07-22	Fujisawa Pharmaceutical Co., Ltd.	Substituted-phenyl substituted-alkyl ethers and the preparation thereof

1975
- 1975-05-22 GB GB2210075A patent/GB1503953A/en not_active Expired
- 1975-06-03 DK DK248875A patent/DK248875A/da not_active Application Discontinuation
- 1975-06-04 CH CH719775A patent/CH613940A5/xx not_active IP Right Cessation
- 1975-06-04 DE DE19752524865 patent/DE2524865A1/de not_active Withdrawn
- 1975-06-04 AU AU81855/75A patent/AU8185575A/en not_active Expired
- 1975-06-04 FR FR7517497A patent/FR2273518A1/fr active Granted
- 1975-06-04 CA CA228,557A patent/CA1050985A/en not_active Expired

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AU2003245963B2 (en) *	2002-06-20	2008-06-26	Smithkline Beecham Corporation	Propionic acid derivatives and their use as hPPARs activators
AU2003245963C1 (en) *	2002-06-20	2008-12-11	Smithkline Beecham Corporation	Propionic acid derivatives and their use as hPPARs activators

Also Published As

Publication number	Publication date
GB1503953A (en)	1978-03-15
DE2524865A1 (de)	1976-01-02
AU8185575A (en)	1976-12-09
FR2273518B1 (da)	1978-10-06
CH613940A5 (en)	1979-10-31
FR2273518A1 (fr)	1976-01-02
DK248875A (da)	1975-12-05

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AU2004213616B2 (en)	2011-05-26	A process of preparing imatinib
SU820659A3 (ru)	1981-04-07	Способ получени производных 4-амино- 5-АлКилСульфОНилОАНизАМидОВ, иХ СОлЕй,ОКиСЕй, лЕВО- и пРАВОВРАщАющиХизОМЕРОВ /иХ ВАРиАНТы/
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DE69226157T2 (de)	1998-10-22	Antiallergische, entzündungshemmende und anti-PAF Pyridazinverbindungen
JP2674199B2 (ja)	1997-11-12	二環式アミン化合物およびその製造法
US4214094A (en)	1980-07-22	Substituted-phenyl substituted-alkyl ethers and the preparation thereof
AU612990B2 (en)	1991-07-25	Antibiotic compounds
FR2557111A1 (fr)	1985-06-28	Nouveaux derives ortho-condenses du pyrrole, leur preparation et les medicaments qui les contiennent
CA1050985A (en)	1979-03-20	Substituted-phenyl substituted-alkyl ethers and the preparation thereof
EP0357126B1 (en)	1994-04-27	Tetracyclic antidepressants
JPH0676407B2 (ja)	1994-09-28	２‐アルコキシ‐ｎ‐（１‐アザビシクロ〔２，２，２〕オクタン‐３‐イル）アミノベンズアミドの製法
US4613599A (en)	1986-09-23	Method of treating thrombotic disease with pyridazinones
CN117769547A (zh)	2024-03-26	3-芳氧基-3-五元杂芳基-丙胺类化合物的制备方法
US4147698A (en)	1979-04-03	3-(Heterocyclicalkylamino)benzisothiazole-1,1-dioxides
FR2539417A1 (fr)	1984-07-20	Nouveaux pyrrolo-1, 2 heterocycles, leur preparation et les medicaments qui les contiennent
KR870001362B1 (ko)	1987-07-20	테트라하이드로 이미다조퀴나졸리논 유도체의 제조방법
CA1102307A (en)	1981-06-02	2-lower alkyl-7-substituted amino-2 or 3-cephem-4- carboxylic acid compounds and processes for preparation thereof
JPS60105672A (ja)	1985-06-11	胃抗分泌剤としてのチアトリアジンジオキサイド類
JPH045289A (ja)	1992-01-09	アミド化合物
CA2049490A1 (en)	1992-03-01	Pyrrolobenzimidazoles, imidazobenzoxazinones and imidazoquinolones, process for their preparation and their use and preparations containing the compounds
FR2496666A1 (fr)	1982-06-25	Nouveaux derives de cephalosporine et composition pharmaceutique les contenant
US4105764A (en)	1978-08-08	4,5-Dihydro-5-oxopyrazolo[1,5-A]quinazoline-3-carboxamides
JPS61126082A (ja)	1986-06-13	アミノピロリジン誘導体、そのエステルおよびその塩
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JPWO1993011123A1 (ja)	1993-12-02	ヘテロ環式化合物及びそれを有効成分とする強心剤