FI62829C - Foerfarande foer framstaellning av fenoletrar anvaendbara saosom laekemedel - Google Patents

Foerfarande foer framstaellning av fenoletrar anvaendbara saosom laekemedel Download PDF

Info

Publication number: FI62829C
Authority: FI; Finland
Prior art keywords: compound; formula; ether; carbon atoms; phenoxy
Prior art date: 1975-11-06

Application number

FI763132A

Other languages

English (en)

Finnish (fi)

Other versions

FI62829B (fi

FI763132A7 (fr

Inventor

Philippe Michel Jacque Manoury

Icilio Angelo Girolamo Cavero

Henry Najer

Don Pierre Rene Luc Giudicelli

Original Assignee

Synthelabo

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.)

1975-11-06

Filing date

1976-11-02

Publication date

1983-03-10

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=9162099&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=FI62829(C) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

1976-11-02 Application filed by Synthelabo filed Critical Synthelabo

1977-05-07 Publication of FI763132A7 publication Critical patent/FI763132A7/fi

1982-11-30 Publication of FI62829B publication Critical patent/FI62829B/fi

1983-03-10 Application granted granted Critical

1983-03-10 Publication of FI62829C publication Critical patent/FI62829C/fi

Links

150000001875 compounds Chemical class 0.000 claims description 79
-1 phenolic ethers Chemical class 0.000 claims description 45
239000000460 chlorine Substances 0.000 claims description 31
239000000203 mixture Substances 0.000 claims description 23
125000004432 carbon atom Chemical group C* 0.000 claims description 15
238000002360 preparation method Methods 0.000 claims description 15
150000003839 salts Chemical class 0.000 claims description 10
238000000034 method Methods 0.000 claims description 9
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 7
239000002253 acid Substances 0.000 claims description 7
229910052760 oxygen Inorganic materials 0.000 claims description 7
150000002118 epoxides Chemical class 0.000 claims description 6
125000000217 alkyl group Chemical group 0.000 claims description 5
125000005843 halogen group Chemical group 0.000 claims description 4
239000001301 oxygen Substances 0.000 claims description 4
229910052717 sulfur Chemical group 0.000 claims description 4
125000002252 acyl group Chemical group 0.000 claims description 3
229910052801 chlorine Inorganic materials 0.000 claims description 3
125000004966 cyanoalkyl group Chemical group 0.000 claims description 3
230000003287 optical effect Effects 0.000 claims description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
125000004434 sulfur atom Chemical group 0.000 claims description 3
150000001412 amines Chemical class 0.000 claims description 2
125000004430 oxygen atom Chemical group O* 0.000 claims description 2
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 claims 4
235000012000 cholesterol Nutrition 0.000 claims 2
240000007124 Brassica oleracea Species 0.000 claims 1
235000003899 Brassica oleracea var acephala Nutrition 0.000 claims 1
235000011301 Brassica oleracea var capitata Nutrition 0.000 claims 1
235000001169 Brassica oleracea var oleracea Nutrition 0.000 claims 1
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims 1
LRMHFDNWKCSEQU-UHFFFAOYSA-N ethoxyethane;phenol Chemical compound CCOCC.OC1=CC=CC=C1 LRMHFDNWKCSEQU-UHFFFAOYSA-N 0.000 claims 1
238000009472 formulation Methods 0.000 claims 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 144
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 52
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 51
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 51
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 48
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 38
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 27
239000011541 reaction mixture Substances 0.000 description 27
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 24
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 17
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 17
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 17
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
238000004458 analytical method Methods 0.000 description 16
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 15
235000019441 ethanol Nutrition 0.000 description 15
239000002904 solvent Substances 0.000 description 15
238000003756 stirring Methods 0.000 description 15
238000010992 reflux Methods 0.000 description 14
JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 13
239000012071 phase Substances 0.000 description 13
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
229910052943 magnesium sulfate Inorganic materials 0.000 description 12
235000019341 magnesium sulphate Nutrition 0.000 description 12
239000002244 precipitate Substances 0.000 description 12
229910052938 sodium sulfate Inorganic materials 0.000 description 12
235000011152 sodium sulphate Nutrition 0.000 description 12
239000007858 starting material Substances 0.000 description 12
238000004821 distillation Methods 0.000 description 11
238000009835 boiling Methods 0.000 description 9
239000007789 gas Substances 0.000 description 9
239000003208 petroleum Substances 0.000 description 9
239000000725 suspension Substances 0.000 description 9
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 8
238000006243 chemical reaction Methods 0.000 description 8
229910052757 nitrogen Inorganic materials 0.000 description 8
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 8
GKIPXFAANLTWBM-UHFFFAOYSA-N epibromohydrin Chemical compound BrCC1CO1 GKIPXFAANLTWBM-UHFFFAOYSA-N 0.000 description 7
239000007787 solid Substances 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 6
229910052794 bromium Inorganic materials 0.000 description 6
239000000284 extract Substances 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
239000000741 silica gel Substances 0.000 description 6
229910002027 silica gel Inorganic materials 0.000 description 6
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 5
230000002378 acidificating effect Effects 0.000 description 5
239000003708 ampul Substances 0.000 description 5
239000003814 drug Substances 0.000 description 5
239000007937 lozenge Substances 0.000 description 5
239000000155 melt Substances 0.000 description 5
JCUJAHLWCDISCC-UHFFFAOYSA-N 2-(4-phenylmethoxyphenyl)ethanol Chemical compound C1=CC(CCO)=CC=C1OCC1=CC=CC=C1 JCUJAHLWCDISCC-UHFFFAOYSA-N 0.000 description 4
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-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
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
239000005557 antagonist Substances 0.000 description 4
230000000747 cardiac effect Effects 0.000 description 4
239000003054 catalyst Substances 0.000 description 4
125000000062 cyclohexylmethoxy group Chemical group [H]C([H])(O*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 4
238000006264 debenzylation reaction Methods 0.000 description 4
230000000694 effects Effects 0.000 description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
230000008018 melting Effects 0.000 description 4
238000002844 melting Methods 0.000 description 4
IUBSYMUCCVWXPE-UHFFFAOYSA-N metoprolol Chemical compound COCCC1=CC=C(OCC(O)CNC(C)C)C=C1 IUBSYMUCCVWXPE-UHFFFAOYSA-N 0.000 description 4
229960002237 metoprolol Drugs 0.000 description 4
VYQNWZOUAUKGHI-UHFFFAOYSA-N monobenzone Chemical compound C1=CC(O)=CC=C1OCC1=CC=CC=C1 VYQNWZOUAUKGHI-UHFFFAOYSA-N 0.000 description 4
239000012074 organic phase Substances 0.000 description 4
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 4
AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 4
239000011734 sodium Substances 0.000 description 4
229910052708 sodium Inorganic materials 0.000 description 4
239000000829 suppository Substances 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
VAKJAFXMJNWYFH-UHFFFAOYSA-N 4-[2-(cyclobutylmethylsulfonyl)ethyl]phenol Chemical compound C1=CC(O)=CC=C1CCS(=O)(=O)CC1CCC1 VAKJAFXMJNWYFH-UHFFFAOYSA-N 0.000 description 3
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 3
BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 3
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
239000008346 aqueous phase Substances 0.000 description 3
102000012740 beta Adrenergic Receptors Human genes 0.000 description 3
108010079452 beta Adrenergic Receptors Proteins 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
238000004587 chromatography analysis Methods 0.000 description 3
WPOPOPFNZYPKAV-UHFFFAOYSA-N cyclobutylmethanol Chemical compound OCC1CCC1 WPOPOPFNZYPKAV-UHFFFAOYSA-N 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
238000001914 filtration Methods 0.000 description 3
150000003840 hydrochlorides Chemical class 0.000 description 3
239000001294 propane Substances 0.000 description 3
238000001953 recrystallisation Methods 0.000 description 3
239000012312 sodium hydride Substances 0.000 description 3
229910000104 sodium hydride Inorganic materials 0.000 description 3
238000003786 synthesis reaction Methods 0.000 description 3
JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 2
OXHPTABOQVHKLN-UHFFFAOYSA-N 1-(2-bromoethyl)-4-methoxybenzene Chemical compound COC1=CC=C(CCBr)C=C1 OXHPTABOQVHKLN-UHFFFAOYSA-N 0.000 description 2
JQPOYIQDKUMPLP-UHFFFAOYSA-N 1-(3-cyclopropylpropoxy)-4-phenylmethoxybenzene Chemical compound C1CC1CCCOC(C=C1)=CC=C1OCC1=CC=CC=C1 JQPOYIQDKUMPLP-UHFFFAOYSA-N 0.000 description 2
LKGKKNVEHPUOGK-UHFFFAOYSA-N 1-[4-[2-(cyclopropylmethylsulfonyl)ethoxy]phenoxy]-3-(propan-2-ylamino)propan-2-ol Chemical compound C1=CC(OCC(O)CNC(C)C)=CC=C1OCCS(=O)(=O)CC1CC1 LKGKKNVEHPUOGK-UHFFFAOYSA-N 0.000 description 2
OUUYFVMQRFVQNJ-UHFFFAOYSA-N 2-(4-methoxyphenyl)ethanethiol Chemical compound COC1=CC=C(CCS)C=C1 OUUYFVMQRFVQNJ-UHFFFAOYSA-N 0.000 description 2
AUWDOZOUJWEPBA-UHFFFAOYSA-N 2-(4-methoxyphenyl)ethanol Chemical compound COC1=CC=C(CCO)C=C1 AUWDOZOUJWEPBA-UHFFFAOYSA-N 0.000 description 2
CACHITVLPUCLIA-UHFFFAOYSA-N 3-cyclopropylpropyl methanesulfonate Chemical compound CS(=O)(=O)OCCCC1CC1 CACHITVLPUCLIA-UHFFFAOYSA-N 0.000 description 2
PIDUCSFTFXWMIL-UHFFFAOYSA-N 4-(3-cyclopropylpropoxy)phenol Chemical compound C1=CC(O)=CC=C1OCCCC1CC1 PIDUCSFTFXWMIL-UHFFFAOYSA-N 0.000 description 2
QEFZFASAZLTLEU-UHFFFAOYSA-N 4-(cyclopropylmethoxy)phenol Chemical compound C1=CC(O)=CC=C1OCC1CC1 QEFZFASAZLTLEU-UHFFFAOYSA-N 0.000 description 2
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
208000024172 Cardiovascular disease Diseases 0.000 description 2
241000699670 Mus sp. Species 0.000 description 2
PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 description 2
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
239000004480 active ingredient Substances 0.000 description 2
230000007059 acute toxicity Effects 0.000 description 2
231100000403 acute toxicity Toxicity 0.000 description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
AEILLAXRDHDKDY-UHFFFAOYSA-N bromomethylcyclopropane Chemical compound BrCC1CC1 AEILLAXRDHDKDY-UHFFFAOYSA-N 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
238000009833 condensation Methods 0.000 description 2
230000005494 condensation Effects 0.000 description 2
125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 description 2
238000004090 dissolution Methods 0.000 description 2
229940079593 drug Drugs 0.000 description 2
210000002216 heart Anatomy 0.000 description 2
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
229910000041 hydrogen chloride Inorganic materials 0.000 description 2
238000005984 hydrogenation reaction Methods 0.000 description 2
229960001317 isoprenaline Drugs 0.000 description 2
239000012280 lithium aluminium hydride Substances 0.000 description 2
230000007935 neutral effect Effects 0.000 description 2
239000008194 pharmaceutical composition Substances 0.000 description 2
238000000746 purification Methods 0.000 description 2
102000005962 receptors Human genes 0.000 description 2
108020003175 receptors Proteins 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
229910000029 sodium carbonate Inorganic materials 0.000 description 2
235000017550 sodium carbonate Nutrition 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 2
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
238000005303 weighing Methods 0.000 description 2
ZQTYOZAGOYYBIG-UHFFFAOYSA-N (2-chloro-1-methylsulfanylethyl)cyclopropane Chemical compound CSC(CCl)C1CC1 ZQTYOZAGOYYBIG-UHFFFAOYSA-N 0.000 description 1
STAGOOBVVAYPOT-WXXKFALUSA-N (e)-but-2-enedioic acid;1-(tert-butylamino)-3-[4-[2-(cyclopropylmethoxy)ethoxy]phenoxy]propan-2-ol Chemical compound OC(=O)\C=C\C(O)=O.C1=CC(OCC(O)CNC(C)(C)C)=CC=C1OCCOCC1CC1.C1=CC(OCC(O)CNC(C)(C)C)=CC=C1OCCOCC1CC1 STAGOOBVVAYPOT-WXXKFALUSA-N 0.000 description 1
QPFMBFXGICFDMW-UHFFFAOYSA-N 1-(2-cyclopropyl-4-propoxyphenoxy)-3-(propan-2-ylamino)propan-2-ol Chemical compound C1(CC1)C1=C(OCC(CNC(C)C)O)C=CC(=C1)OCCC QPFMBFXGICFDMW-UHFFFAOYSA-N 0.000 description 1
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RIEYOMHHXYUYMJ-UHFFFAOYSA-N 1-(cyclopropylmethoxy)-4-phenylmethoxybenzene Chemical compound C1CC1COC(C=C1)=CC=C1OCC1=CC=CC=C1 RIEYOMHHXYUYMJ-UHFFFAOYSA-N 0.000 description 1
NLQAVTXHOAUVIG-UHFFFAOYSA-N 1-(cyclopropylmethoxymethyl)-4-phenylmethoxybenzene Chemical compound C1CC1COCC(C=C1)=CC=C1OCC1=CC=CC=C1 NLQAVTXHOAUVIG-UHFFFAOYSA-N 0.000 description 1
CXWINRXVQAYXIB-UHFFFAOYSA-N 1-(tert-butylamino)-3-[4-(cyclopropylmethoxy)phenoxy]propan-2-ol Chemical compound C1=CC(OCC(O)CNC(C)(C)C)=CC=C1OCC1CC1 CXWINRXVQAYXIB-UHFFFAOYSA-N 0.000 description 1
FKJPQKYUSLNOLX-UHFFFAOYSA-N 1-(tert-butylamino)-3-[4-[2-(cyclopropylmethoxy)ethoxy]phenoxy]propan-2-ol Chemical compound C1=CC(OCC(O)CNC(C)(C)C)=CC=C1OCCOCC1CC1 FKJPQKYUSLNOLX-UHFFFAOYSA-N 0.000 description 1
IIXNLBZVLPIFQL-UHFFFAOYSA-N 1-[2-(cyclobutylmethoxy)ethyl]-4-phenylmethoxybenzene Chemical compound C1CCC1COCCC(C=C1)=CC=C1OCC1=CC=CC=C1 IIXNLBZVLPIFQL-UHFFFAOYSA-N 0.000 description 1
GBVJBARYIFJWSW-UHFFFAOYSA-N 1-[2-(cyclobutylmethylsulfanyl)ethyl]-4-methoxybenzene Chemical compound C1=CC(OC)=CC=C1CCSCC1CCC1 GBVJBARYIFJWSW-UHFFFAOYSA-N 0.000 description 1
DQJKRZAQGKJXSY-UHFFFAOYSA-N 1-[2-(cyclopropylmethoxy)ethoxy]-4-phenylmethoxybenzene Chemical compound C1CC1COCCOC(C=C1)=CC=C1OCC1=CC=CC=C1 DQJKRZAQGKJXSY-UHFFFAOYSA-N 0.000 description 1
GYJXNKHOFIHFEE-UHFFFAOYSA-N 1-[4-(3-cyclopropylpropoxy)phenoxy]-3-(propan-2-ylamino)propan-2-ol Chemical compound C1=CC(OCC(O)CNC(C)C)=CC=C1OCCCC1CC1 GYJXNKHOFIHFEE-UHFFFAOYSA-N 0.000 description 1
BGTPDTUZXVFKOP-UHFFFAOYSA-N 1-[4-(cyclopropylmethoxy)phenoxy]-3-(propan-2-ylamino)propan-2-ol Chemical compound C1=CC(OCC(O)CNC(C)C)=CC=C1OCC1CC1 BGTPDTUZXVFKOP-UHFFFAOYSA-N 0.000 description 1
LCDAELAZMVDIGV-UHFFFAOYSA-N 1-[4-[2-(cyclobutylmethoxy)ethoxy]phenoxy]-3-(propan-2-ylamino)propan-2-ol Chemical compound C1=CC(OCC(O)CNC(C)C)=CC=C1OCCOCC1CCC1 LCDAELAZMVDIGV-UHFFFAOYSA-N 0.000 description 1
RMBHCLXFPKGGOX-UHFFFAOYSA-N 1-[4-[2-(cyclobutylmethylsulfanyl)ethyl]phenoxy]-3-(propan-2-ylamino)propan-2-ol Chemical compound C1=CC(OCC(O)CNC(C)C)=CC=C1CCSCC1CCC1 RMBHCLXFPKGGOX-UHFFFAOYSA-N 0.000 description 1
ZAOXCWMNIYUNPJ-UHFFFAOYSA-N 1-[4-[2-(cyclobutylmethylsulfonyl)ethyl]phenoxy]-3-(propan-2-ylamino)propan-2-ol Chemical compound C1=CC(OCC(O)CNC(C)C)=CC=C1CCS(=O)(=O)CC1CCC1 ZAOXCWMNIYUNPJ-UHFFFAOYSA-N 0.000 description 1
UCXOQUOLTMEKEK-UHFFFAOYSA-N 1-[4-[2-(cyclopropylmethylsulfanyl)ethoxy]phenoxy]-3-(propan-2-ylamino)propan-2-ol Chemical compound C1=CC(OCC(O)CNC(C)C)=CC=C1OCCSCC1CC1 UCXOQUOLTMEKEK-UHFFFAOYSA-N 0.000 description 1
ZVTCOQDWIJYYSQ-UHFFFAOYSA-N 1-cyclopropylpropan-1-ol Chemical compound CCC(O)C1CC1 ZVTCOQDWIJYYSQ-UHFFFAOYSA-N 0.000 description 1
HDNRAPAFJLXKBV-UHFFFAOYSA-N 1-ethyl-4-methoxybenzene Chemical compound CCC1=CC=C(OC)C=C1 HDNRAPAFJLXKBV-UHFFFAOYSA-N 0.000 description 1
XKZQKPRCPNGNFR-UHFFFAOYSA-N 2-(3-hydroxyphenyl)phenol Chemical compound OC1=CC=CC(C=2C(=CC=CC=2)O)=C1 XKZQKPRCPNGNFR-UHFFFAOYSA-N 0.000 description 1
LYDDUHIGQQYFRB-UHFFFAOYSA-N 2-(cyclopropylmethoxy)ethyl methanesulfonate Chemical compound CS(=O)(=O)OCCOCC1CC1 LYDDUHIGQQYFRB-UHFFFAOYSA-N 0.000 description 1
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
OECSXVUMQWZYSI-UHFFFAOYSA-N 2-[4-[2-(cyclopropylmethoxy)ethyl]phenoxy]-1-(propan-2-ylamino)propan-2-ol Chemical compound C1=CC(OC(C)(O)CNC(C)C)=CC=C1CCOCC1CC1 OECSXVUMQWZYSI-UHFFFAOYSA-N 0.000 description 1
JWDYSWINTVYGKA-UHFFFAOYSA-N 2-[[4-(3-cyclopropylpropoxy)phenoxy]methyl]oxirane Chemical compound C1CC1CCCOC(C=C1)=CC=C1OCC1CO1 JWDYSWINTVYGKA-UHFFFAOYSA-N 0.000 description 1
LRJMVTDXOWJMFV-UHFFFAOYSA-N 2-[[4-[2-(cyclobutylmethoxy)ethoxy]phenoxy]methyl]oxirane Chemical compound C1CCC1COCCOC(C=C1)=CC=C1OCC1CO1 LRJMVTDXOWJMFV-UHFFFAOYSA-N 0.000 description 1
RSYSGZSYFPXHTK-UHFFFAOYSA-N 2-[[4-[2-(cyclobutylmethoxy)ethyl]phenoxy]methyl]oxirane Chemical compound C1CCC1COCCC(C=C1)=CC=C1OCC1CO1 RSYSGZSYFPXHTK-UHFFFAOYSA-N 0.000 description 1
AJPUELIJKUJCKU-UHFFFAOYSA-N 2-[[4-[2-(cyclobutylmethylsulfanyl)ethyl]phenoxy]methyl]oxirane Chemical compound C1CCC1CSCCC(C=C1)=CC=C1OCC1CO1 AJPUELIJKUJCKU-UHFFFAOYSA-N 0.000 description 1
LJJGWRBHXPKJIS-UHFFFAOYSA-N 2-[[4-[2-(cyclobutylmethylsulfonyl)ethyl]phenoxy]methyl]oxirane Chemical compound C1CCC1CS(=O)(=O)CCC(C=C1)=CC=C1OCC1CO1 LJJGWRBHXPKJIS-UHFFFAOYSA-N 0.000 description 1
QVROXVNLMUDQGX-UHFFFAOYSA-N 2-[[4-[2-(cyclopropylmethylsulfanyl)ethoxy]phenoxy]methyl]oxirane Chemical compound C=1C=C(OCC2OC2)C=CC=1OCCSCC1CC1 QVROXVNLMUDQGX-UHFFFAOYSA-N 0.000 description 1
125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
VCZKBHBDBKAYKG-UHFFFAOYSA-N 3-(2-hydroxypropylamino)butanenitrile Chemical compound CC(O)CNC(C)CC#N VCZKBHBDBKAYKG-UHFFFAOYSA-N 0.000 description 1
PPBSMPOYVPZOFM-UHFFFAOYSA-N 3-aminobutanenitrile Chemical compound CC(N)CC#N PPBSMPOYVPZOFM-UHFFFAOYSA-N 0.000 description 1
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
BKLXBPOLDMLLQX-UHFFFAOYSA-N 4-(1-cyclopropylpropoxy)phenol Chemical compound C1CC1C(CC)OC1=CC=C(O)C=C1 BKLXBPOLDMLLQX-UHFFFAOYSA-N 0.000 description 1
UJHWFZDWDSPZGV-UHFFFAOYSA-N 4-(cyclopropylmethoxymethyl)phenol Chemical compound C1=CC(O)=CC=C1COCC1CC1 UJHWFZDWDSPZGV-UHFFFAOYSA-N 0.000 description 1
OEBIVOHKFYSBPE-UHFFFAOYSA-N 4-Benzyloxybenzyl alcohol Chemical compound C1=CC(CO)=CC=C1OCC1=CC=CC=C1 OEBIVOHKFYSBPE-UHFFFAOYSA-N 0.000 description 1
OIPNKHUWTKZMQO-UHFFFAOYSA-N 4-[2-(cyclobutylmethoxy)ethyl]phenol Chemical compound C1=CC(O)=CC=C1CCOCC1CCC1 OIPNKHUWTKZMQO-UHFFFAOYSA-N 0.000 description 1
LMJPPRYGGYSBMK-UHFFFAOYSA-N 4-[2-(cyclobutylmethylsulfanyl)ethyl]phenol Chemical compound C1=CC(O)=CC=C1CCSCC1CCC1 LMJPPRYGGYSBMK-UHFFFAOYSA-N 0.000 description 1
WNEQFDSWDCYKOE-UHFFFAOYSA-N 4-[2-(cyclopropylmethoxy)ethyl]phenol Chemical compound C1=CC(O)=CC=C1CCOCC1CC1 WNEQFDSWDCYKOE-UHFFFAOYSA-N 0.000 description 1
NRPFNQUDKRYCNX-UHFFFAOYSA-N 4-methoxyphenylacetic acid Chemical compound COC1=CC=C(CC(O)=O)C=C1 NRPFNQUDKRYCNX-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
101000608750 Arachis hypogaea Alpha-methyl-mannoside-specific lectin Proteins 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
PALSNJZKDYLKNO-UHFFFAOYSA-N C1(CC1)CCCOC1=C(C=CC=C1)O Chemical compound C1(CC1)CCCOC1=C(C=CC=C1)O PALSNJZKDYLKNO-UHFFFAOYSA-N 0.000 description 1
FCIXKFITTZHDLN-UHFFFAOYSA-N C1(CC1)CSCCOC1=CC=C(OCC(CNCCC)O)C=C1 Chemical compound C1(CC1)CSCCOC1=CC=C(OCC(CNCCC)O)C=C1 FCIXKFITTZHDLN-UHFFFAOYSA-N 0.000 description 1
HDNAVONIESEULU-UHFFFAOYSA-N C1CCC1COCCOC(C=C1)=CC=C1OCC1=CC=CC=C1 Chemical compound C1CCC1COCCOC(C=C1)=CC=C1OCC1=CC=CC=C1 HDNAVONIESEULU-UHFFFAOYSA-N 0.000 description 1
241001070941 Castanea Species 0.000 description 1
235000014036 Castanea Nutrition 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
101150065749 Churc1 gene Proteins 0.000 description 1
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WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical group CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
DTAFLBZLAZYRDX-UHFFFAOYSA-N OOOOOO Chemical compound OOOOOO DTAFLBZLAZYRDX-UHFFFAOYSA-N 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
102100038239 Protein Churchill Human genes 0.000 description 1
241000700159 Rattus Species 0.000 description 1
235000004789 Rosa xanthina Nutrition 0.000 description 1
241000109329 Rosa xanthina Species 0.000 description 1
208000001871 Tachycardia Diseases 0.000 description 1
101000771730 Tropidolaemus wagleri Waglerin-3 Proteins 0.000 description 1
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
238000010171 animal model Methods 0.000 description 1
230000002180 anti-stress Effects 0.000 description 1
MVYYDFCVPLFOKV-UHFFFAOYSA-M barium monohydroxide Chemical compound [Ba]O MVYYDFCVPLFOKV-UHFFFAOYSA-M 0.000 description 1
KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
229940073608 benzyl chloride Drugs 0.000 description 1
239000002981 blocking agent Substances 0.000 description 1
239000002775 capsule Substances 0.000 description 1
150000001721 carbon Chemical group 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
JNDJPKHYZWRRIS-UHFFFAOYSA-N cicloprolol Chemical compound C1=CC(OCC(O)CNC(C)C)=CC=C1OCCOCC1CC1 JNDJPKHYZWRRIS-UHFFFAOYSA-N 0.000 description 1
229910052681 coesite Inorganic materials 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
239000013256 coordination polymer Substances 0.000 description 1
210000004351 coronary vessel Anatomy 0.000 description 1
229910052906 cristobalite Inorganic materials 0.000 description 1
FKGIKRMZMCYOAL-UHFFFAOYSA-N cyclobutylmethyl methanesulfonate Chemical compound CS(=O)(=O)OCC1CCC1 FKGIKRMZMCYOAL-UHFFFAOYSA-N 0.000 description 1
IABZFPLSDXDLRS-UHFFFAOYSA-N cyclohexylmethyl methanesulfonate Chemical compound CS(=O)(=O)OCC1CCCCC1 IABZFPLSDXDLRS-UHFFFAOYSA-N 0.000 description 1
GUDMZGLFZNLYEY-UHFFFAOYSA-N cyclopropylmethanol Chemical compound OCC1CC1 GUDMZGLFZNLYEY-UHFFFAOYSA-N 0.000 description 1
210000003298 dental enamel Anatomy 0.000 description 1
150000004985 diamines Chemical class 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
229910001873 dinitrogen Inorganic materials 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
231100000673 dose–response relationship Toxicity 0.000 description 1
239000008298 dragée Substances 0.000 description 1
210000005069 ears Anatomy 0.000 description 1
230000002526 effect on cardiovascular system Effects 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
239000012259 ether extract Substances 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
LBAQSKZHMLAFHH-UHFFFAOYSA-N ethoxyethane;hydron;chloride Chemical compound Cl.CCOCC LBAQSKZHMLAFHH-UHFFFAOYSA-N 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000008103 glucose Substances 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
238000000265 homogenisation Methods 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
239000012535 impurity Substances 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
238000005342 ion exchange Methods 0.000 description 1
231100000636 lethal dose Toxicity 0.000 description 1
230000031864 metaphase Effects 0.000 description 1
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
239000011707 mineral Substances 0.000 description 1
239000003595 mist Substances 0.000 description 1
230000004118 muscle contraction Effects 0.000 description 1
210000004165 myocardium Anatomy 0.000 description 1
210000000056 organ Anatomy 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
235000010603 pastilles Nutrition 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
LJCNRYVRMXRIQR-OLXYHTOASA-L potassium sodium L-tartrate Chemical compound [Na+].[K+].[O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O LJCNRYVRMXRIQR-OLXYHTOASA-L 0.000 description 1
150000003141 primary amines Chemical class 0.000 description 1
239000000047 product Substances 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
150000003385 sodium Chemical class 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
239000001476 sodium potassium tartrate Substances 0.000 description 1
235000011006 sodium potassium tartrate Nutrition 0.000 description 1
239000012265 solid product Substances 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
229910052682 stishovite Inorganic materials 0.000 description 1
239000000126 substance Substances 0.000 description 1
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
239000003826 tablet Substances 0.000 description 1
230000006794 tachycardia Effects 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
231100001274 therapeutic index Toxicity 0.000 description 1
229910052905 tridymite Inorganic materials 0.000 description 1
ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
238000001665 trituration Methods 0.000 description 1
230000002792 vascular Effects 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/18—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by etherified hydroxyl radicals
- C07D303/20—Ethers with hydroxy compounds containing no oxirane rings
- C07D303/24—Ethers with hydroxy compounds containing no oxirane rings with polyhydroxy compounds
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/06—Antiarrhythmics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/08—Vasodilators for multiple indications
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Veterinary Medicine (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Animal Behavior & Ethology (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Heart & Thoracic Surgery (AREA)
Cardiology (AREA)
Vascular Medicine (AREA)
Urology & Nephrology (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Steroid Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Macromonomer-Based Addition Polymer (AREA)

FI763132A 1975-11-06 1976-11-02 Foerfarande foer framstaellning av fenoletrar anvaendbara saosom laekemedel FI62829C (fi)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
FR7533899		1975-11-06
FR7533899A FR2330383A1 (fr)	1975-11-06	1975-11-06	Nouveaux ethers de phenols substitues, leurs sels, leur preparation et les medicaments qui les renferment

Publications (3)

Publication Number	Publication Date
FI763132A7 FI763132A7 (fr)	1977-05-07
FI62829B FI62829B (fi)	1982-11-30
FI62829C true FI62829C (fi)	1983-03-10

Family

ID=9162099

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
FI763132A FI62829C (fi)	1975-11-06	1976-11-02	Foerfarande foer framstaellning av fenoletrar anvaendbara saosom laekemedel

Country Status (24)

Country	Link
US (2)	US4252984A (fr)
JP (1)	JPS5848543B2 (fr)
AR (1)	AR214303A1 (fr)
AT (1)	AT344683B (fr)
AU (1)	AU501581B2 (fr)
BE (1)	BE847801A (fr)
CA (1)	CA1072981A (fr)
CH (1)	CH602582A5 (fr)
DE (1)	DE2649605C3 (fr)
DK (1)	DK145119C (fr)
ES (1)	ES452920A1 (fr)
FI (1)	FI62829C (fr)
FR (1)	FR2330383A1 (fr)
GB (1)	GB1515978A (fr)
GR (1)	GR61363B (fr)
IE (1)	IE43645B1 (fr)
IL (1)	IL50814A (fr)
LU (1)	LU76117A1 (fr)
NL (1)	NL179051C (fr)
NO (1)	NO142034C (fr)
NZ (1)	NZ182498A (fr)
PT (1)	PT65780B (fr)
SE (1)	SE433208B (fr)
ZA (1)	ZA766338B (fr)

Families Citing this family (58)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2409980A1 (fr) *	1977-11-24	1979-06-22	Synthelabo	Ethers de phenols et leur application en therapeutique
IT1147311B (it) *	1980-02-13	1986-11-19	Stabil Bioterapico Farmachim	Eteri basici di 4-idrossi-benzofenoni con attivita' quali agenti betabloccanti e relativi procedimento di preparazione
ZW9881A1 (en) *	1980-06-02	1981-12-23	Hoffmann La Roche	Substituted phenoxyaminopropanol derivatives
DE3125870C2 (de) *	1980-07-09	1994-09-15	William John Louis	3-Aminopropoxyphenyl Derivate, ihre Herstellung und sie enthaltende Arzneimittel
CH643527A5 (en) *	1980-10-24	1984-06-15	Ciba Geigy Ag	Process for the preparation of 1-alkylamino-3-(4-(2-lower alkoxy-ethyl)phenoxy)-2-propanols
FI76551C (fi)	1980-11-06	1988-11-10	Sandoz Ag	Foerfarande foer framstaellning av nya terapeutiskt anvaendbara 3-aminopropoxifenylderivat.
JPS57108047A (en) *	1980-11-06	1982-07-05	Sandoz Ag	3-aminopropoxyphenyl derivative, manufacture and pharmaceutical composition containing same
US5347050A (en) *	1980-11-06	1994-09-13	Richard Berthold	3-aminopropoxyphenyl derivatives, their preparation and pharmaceutical compositions containing them
DE3125636A1 (de) *	1981-06-30	1983-01-13	Merck Patent Gmbh, 6100 Darmstadt	1-(p-2-isopropoxyethoxymethyl-phenoxy)-3-isopropylamino-propan-2-ol zur senkung des augeninnendrucks und ophtalmikum, enthalten diese verbindung
FR2512443A1 (fr) *	1981-09-10	1983-03-11	Synthelabo	Derives de phenoxy-3 propanol-2, leur preparation et leur application en therapeutique
DE3151201A1 (de) *	1981-12-23	1983-07-28	Beiersdorf Ag, 2000 Hamburg	Substituierte phenoxyalkanolamine und phenoxyalkanol-cycloalkylamine, verfahren zu ihrer herstellung, diese verbindungen enthaltende pharmazeutische zubereitungen und zwischenprodukte
US4450172A (en) *	1982-03-10	1984-05-22	E. I. Du Pont De Nemours And Company	Antihypertensive polyhalohydroxyisopropyl phenylalka(e)noic acid esters of alkylaminohydroxypropyloxyphenylalkyl alcohols
FR2536390B1 (fr) *	1982-11-22	1986-03-21	Synthelabo	Isomere s du betaxolol, sa preparation et son application en therapeutique
CA1262729A (fr) *	1983-10-19	1989-11-07	Leo Alig	Phenoxypropanolamines
US5166218A (en) *	1983-10-19	1992-11-24	Hoffmann-La Roche Inc.	Phenoxypropanolamines and pharmaceutical compositions thereof
ZA852843B (en) *	1984-05-15	1985-11-27	Warner Lambert Co	Bevantolol preparation
GB8412864D0 (en) *	1984-05-19	1984-06-27	Smith Kline French Lab	Chemical compounds
US5554367A (en) *	1984-10-31	1996-09-10	Alcon Laboratories, Inc.	Compositions for treatment of glaucoma
ES8609190A1 (es) *	1985-02-07	1986-07-16	Pharma Investi S A	Un procedimiento para preparar eteres fenolicos
US5095151A (en) *	1985-05-21	1992-03-10	American Home Products Corporation	Preparation of propranolol hydrochloride macrocrystals
EP0252007A3 (fr) *	1986-06-28	1989-07-05	Ciba-Geigy Ag	Dérivés de 2-propanol comme inhibiteurs de corrosion
US4694022A (en) *	1986-12-24	1987-09-15	Alcon Laboratories, Inc.	Fatty acid salts of betaxolol useful in the treatment of glaucoma
DE3866984D1 (en) *	1987-07-21	1992-01-30	Hoffmann La Roche	Phenoxypropanolamine.
FR2672594B1 (fr) *	1991-02-08	1994-07-01	Synthelabo	Derives d'ethers de phenols, leur preparation et leur application en therapeutique.
US6627662B2 (en)	1995-10-10	2003-09-30	William John Louis, Austin And Repatriation Medical Centre	3-amino-propoxyphenyl derivatives (I)
CA2193149C (fr) *	1995-12-22	2002-04-23	David H. Donabedian	Systemes cationiques therapeutiques
US5942633A (en) *	1996-06-19	1999-08-24	Abbott Laboratories	Process for the selective alkylation of betaxolol intermediates
US5731463A (en) *	1996-09-23	1998-03-24	Abbott Laboratories	Selective alkylation of an alcohol substituted phenol compound
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1975
- 1975-11-06 FR FR7533899A patent/FR2330383A1/fr active Granted
1976
- 1976-10-20 US US05/734,359 patent/US4252984A/en not_active Expired - Lifetime
- 1976-10-25 ZA ZA766338A patent/ZA766338B/xx unknown
- 1976-10-29 DE DE2649605A patent/DE2649605C3/de not_active Expired
- 1976-10-29 BE BE171927A patent/BE847801A/fr not_active IP Right Cessation
- 1976-11-02 GB GB45560/76A patent/GB1515978A/en not_active Expired
- 1976-11-02 GR GR52068A patent/GR61363B/el unknown
- 1976-11-02 DK DK495476A patent/DK145119C/da not_active IP Right Cessation
- 1976-11-02 IE IE2435/76A patent/IE43645B1/en not_active IP Right Cessation
- 1976-11-02 AT AT812076A patent/AT344683B/de active
- 1976-11-02 PT PT65780A patent/PT65780B/fr unknown
- 1976-11-02 NO NO763732A patent/NO142034C/no unknown
- 1976-11-02 ES ES452920A patent/ES452920A1/es not_active Expired
- 1976-11-02 NL NLAANVRAGE7612123,A patent/NL179051C/xx not_active IP Right Cessation
- 1976-11-02 SE SE7612177A patent/SE433208B/xx active Protection Beyond IP Right Term
- 1976-11-02 CA CA264,650A patent/CA1072981A/fr not_active Expired
- 1976-11-02 AR AR265315A patent/AR214303A1/es active
- 1976-11-02 FI FI763132A patent/FI62829C/fi not_active IP Right Cessation
- 1976-11-02 AU AU19259/76A patent/AU501581B2/en not_active Expired
- 1976-11-02 CH CH1380076A patent/CH602582A5/xx not_active IP Right Cessation
- 1976-11-02 NZ NZ182498A patent/NZ182498A/xx unknown
- 1976-11-02 IL IL50814A patent/IL50814A/xx unknown
- 1976-11-02 JP JP51133144A patent/JPS5848543B2/ja not_active Expired
- 1976-11-03 LU LU76117A patent/LU76117A1/xx unknown
1979
- 1979-03-14 US US06/020,463 patent/US4311708A/en not_active Expired - Lifetime

Also Published As

Publication number	Publication date
DK145119C (da)	1983-02-14
NO142034B (no)	1980-03-10
AT344683B (de)	1978-08-10
FI62829B (fi)	1982-11-30
DE2649605C3 (de)	1981-04-02
LU76117A1 (fr)	1978-07-10
AR214303A1 (es)	1979-05-31
IL50814A0 (en)	1977-01-31
IL50814A (en)	1979-11-30
ZA766338B (en)	1977-10-26
JPS5285146A (en)	1977-07-15
DK495476A (da)	1977-05-07
SE7612177L (sv)	1977-05-07
GB1515978A (en)	1978-06-28
IE43645B1 (en)	1981-04-22
US4311708A (en)	1982-01-19
SE433208B (sv)	1984-05-14
FI763132A7 (fr)	1977-05-07
GR61363B (en)	1978-10-30
FR2330383B1 (fr)	1979-09-21
NO763732L (no)	1977-05-09
IE43645L (en)	1977-05-06
DK145119B (da)	1982-09-06
DE2649605A1 (de)	1977-05-18
PT65780B (fr)	1978-05-10
NO142034C (no)	1980-06-18
NZ182498A (en)	1978-04-03
CH602582A5 (fr)	1978-07-31
NL7612123A (nl)	1977-05-10
ATA812076A (de)	1977-12-15
FR2330383A1 (fr)	1977-06-03
CA1072981A (fr)	1980-03-04
JPS5848543B2 (ja)	1983-10-28
NL179051C (nl)	1986-07-01
AU1925976A (en)	1978-05-11
US4252984A (en)	1981-02-24
NL179051B (nl)	1986-02-03
ES452920A1 (es)	1977-11-01
DE2649605B2 (de)	1980-07-10
AU501581B2 (en)	1979-06-21
PT65780A (fr)	1976-12-01
BE847801A (fr)	1977-02-14

Legal Events

Date	Code	Title	Description
1976-11-02	MA	Patent expired
2004-08-31	MA	Patent expired	Owner name: SYNTHELABO

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DK168484B1 (da)	1994-04-05	Analogifremgangsmåde til fremstilling af phenylethanolaminderivater eller fysiologisk accetable syreadditionssalte deraf
US5491173A (en)	1996-02-13	Tri-phenyl alkene derivatives and their preparation and use
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FI63571B (fi)	1983-03-31	Foerfarande foer framstaellning av analgetiskt verkande racemiska eller diastereomera och optiskt aktiva 2-tetrahydrofurfuryl-(1r/s 5r/s 9r/s)-2'-hydroxi-5,9-dimetyl-6,7-bensomorfaner och deras syraadditionssalter
DE4117512A1 (de)	1992-11-26	2-phenylbenzo(b)furane und -thiophene, verfahren zu deren herstellung und diese enthaltende pharmazeutische praeparate
JPS6089474A (ja)	1985-05-20	モルフイナン誘導体，その製造方法，及び該化合物を含有する抗腫瘍剤
CN102372627B (zh)	2015-05-27	木豆素及其结构类似物的制备方法
FI71123C (fi)	1986-11-24	Analogifoerfarande foer framstaellning av som laekemedel anvaendbar 2-/2'-hydroxi-3'-(1,1-dimetylpropylamino)- propoxi/-beta-fenylpropiofenon och syreadditionssalter av denna
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US3105854A (en)	1963-10-01	Meta-substituted phenoxyethylamines
IL31299A (en)	1972-09-28	Alkyl phenyl ketone derivatives and process for their preparation
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HU193268B (en)	1987-09-28	Process for preparing novel substituted alkane and alkene derivatives
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NZ201859A (en)	1985-05-31	3-phenoxy-1-aminopropan-2-ol derivatives
JPS623150B2 (fr)	1987-01-23
PL82037B1 (fr)	1975-10-31
KR890000021B1 (ko)	1989-03-06	아릴옥시사이클로알칸올 아미노 알킬렌 아릴케톤 및 이의 제조방법
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US3996284A (en)	1976-12-07	Naphthyl and tetrahydronaphthyl di-ethers
DE2053192C3 (de)	1974-02-28	l-Amino-3-phenoxy-propanol-(2)derivate, deren therapeutisch verträgliche Salze und diese enthaltende Arzneimittel
DK141964B (da)	1980-07-28	Analogifremgangsmaade til fremstilling af isoquinolinderivater eller salte deraf med fysiologisk acceptable syrer