DE2711655C2 - - Google Patents
Info
- Publication number
- DE2711655C2 DE2711655C2 DE2711655A DE2711655A DE2711655C2 DE 2711655 C2 DE2711655 C2 DE 2711655C2 DE 2711655 A DE2711655 A DE 2711655A DE 2711655 A DE2711655 A DE 2711655A DE 2711655 C2 DE2711655 C2 DE 2711655C2
- Authority
- DE
- Germany
- Prior art keywords
- benzyl
- methyl
- furo
- dihydro
- pyridin
- Prior art date
- 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
Links
- -1 2-hydroxy-1,3-propylene Chemical group 0.000 claims description 53
- 239000002253 acid Substances 0.000 claims description 27
- 150000003839 salts Chemical class 0.000 claims description 25
- 150000001875 compounds Chemical class 0.000 claims description 19
- 125000004432 carbon atom Chemical group C* 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 14
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 13
- 229910052757 nitrogen Inorganic materials 0.000 claims description 11
- 239000004480 active ingredient Substances 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- 229940124597 therapeutic agent Drugs 0.000 claims description 3
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 2
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 2
- OBEKRAIJYUVRNV-UHFFFAOYSA-N 1-(4-benzyl-6-methyl-1,3-dihydrofuro[3,4-c]pyridin-7-yl)-4-[4-(4-benzyl-6-methyl-1,3-dihydrofuro[3,4-c]pyridin-7-yl)-4-(propan-2-ylamino)butoxy]-n-propan-2-ylbutan-1-amine Chemical compound C=12COCC2=C(CC=2C=CC=CC=2)N=C(C)C=1C(NC(C)C)CCCOCCCC(NC(C)C)C(C(=N1)C)=C2COCC2=C1CC1=CC=CC=C1 OBEKRAIJYUVRNV-UHFFFAOYSA-N 0.000 claims 1
- RLPVJPQFQZRALB-UHFFFAOYSA-N 1-(4-benzyl-6-methyl-1,3-dihydrofuro[3,4-c]pyridin-7-yl)-4-[4-(4-benzyl-6-methyl-1,3-dihydrofuro[3,4-c]pyridin-7-yl)-4-(tert-butylamino)butoxy]-N-tert-butylbutan-1-amine Chemical compound C(C1=CC=CC=C1)C1=NC(=C(C2=C1COC2)C(CCCOCCCC(C=1C2=C(C(=NC=1C)CC1=CC=CC=C1)COC2)NC(C)(C)C)NC(C)(C)C)C RLPVJPQFQZRALB-UHFFFAOYSA-N 0.000 claims 1
- AWQIQYQLFGJJPT-UHFFFAOYSA-N CN(C)C(CCOCCC(C1=C(N=C(C2=C1COC2)CC3=CC=CC=C3)CC4=CC=CC=C4)N(C)C)C5=C(N=C(C6=C5COC6)CC7=CC=CC=C7)CC8=CC=CC=C8 Chemical compound CN(C)C(CCOCCC(C1=C(N=C(C2=C1COC2)CC3=CC=CC=C3)CC4=CC=CC=C4)N(C)C)C5=C(N=C(C6=C5COC6)CC7=CC=CC=C7)CC8=CC=CC=C8 AWQIQYQLFGJJPT-UHFFFAOYSA-N 0.000 claims 1
- 239000012050 conventional carrier Substances 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- 239000002904 solvent Substances 0.000 description 20
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 14
- 150000001412 amines Chemical class 0.000 description 14
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 14
- 239000000203 mixture Substances 0.000 description 13
- 239000000243 solution Substances 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- 238000000034 method Methods 0.000 description 11
- 239000002585 base Substances 0.000 description 10
- ZPHRLPUZKGQIIV-UHFFFAOYSA-N 4-benzyl-6-methyl-1,3-dihydrofuro[3,4-c]pyridin-7-ol Chemical compound C=12COCC2=C(O)C(C)=NC=1CC1=CC=CC=C1 ZPHRLPUZKGQIIV-UHFFFAOYSA-N 0.000 description 9
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- ARGCQEVBJHPOGB-UHFFFAOYSA-N 2,5-dihydrofuran Chemical compound C1OCC=C1 ARGCQEVBJHPOGB-UHFFFAOYSA-N 0.000 description 7
- 230000003288 anthiarrhythmic effect Effects 0.000 description 7
- 150000002431 hydrogen Chemical group 0.000 description 7
- 235000019359 magnesium stearate Nutrition 0.000 description 7
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 description 7
- 239000007858 starting material Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 6
- LOUPRKONTZGTKE-LHHVKLHASA-N quinidine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@H]2[C@@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-LHHVKLHASA-N 0.000 description 6
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 5
- 239000003513 alkali Substances 0.000 description 5
- 239000003416 antiarrhythmic agent Substances 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 159000000000 sodium salts Chemical class 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 4
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 4
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 4
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 4
- 239000000454 talc Substances 0.000 description 4
- 229910052623 talc Inorganic materials 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- YHRUOJUYPBUZOS-UHFFFAOYSA-N 1,3-dichloropropane Chemical compound ClCCCCl YHRUOJUYPBUZOS-UHFFFAOYSA-N 0.000 description 3
- FHFYRJRODNUIKT-UHFFFAOYSA-N 2-benzyl-4-ethyl-1,3-oxazole Chemical compound CCC1=COC(CC=2C=CC=CC=2)=N1 FHFYRJRODNUIKT-UHFFFAOYSA-N 0.000 description 3
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- 229920002261 Corn starch Polymers 0.000 description 3
- 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 3
- 241001465754 Metazoa Species 0.000 description 3
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 239000011230 binding agent Substances 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 description 3
- 239000008120 corn starch Substances 0.000 description 3
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 3
- 239000008298 dragée Substances 0.000 description 3
- PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 3
- 239000008101 lactose Substances 0.000 description 3
- 229960001404 quinidine Drugs 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 239000012312 sodium hydride Substances 0.000 description 3
- 229910000104 sodium hydride Inorganic materials 0.000 description 3
- 229940066768 systemic antihistamines aminoalkyl ethers Drugs 0.000 description 3
- 239000003826 tablet Substances 0.000 description 3
- 238000010626 work up procedure Methods 0.000 description 3
- KJDRSWPQXHESDQ-UHFFFAOYSA-N 1,4-dichlorobutane Chemical compound ClCCCCCl KJDRSWPQXHESDQ-UHFFFAOYSA-N 0.000 description 2
- WQMAANNAZKNUDL-UHFFFAOYSA-N 2-dimethylaminoethyl chloride Chemical compound CN(C)CCCl WQMAANNAZKNUDL-UHFFFAOYSA-N 0.000 description 2
- SVLTYIBILQBQNY-UHFFFAOYSA-N 3-methylsulfonyl-2,5-dihydrofuran Chemical compound CS(=O)(=O)C1=CCOC1 SVLTYIBILQBQNY-UHFFFAOYSA-N 0.000 description 2
- SDDLZCWMXNITJW-UHFFFAOYSA-N 4,6-dibenzyl-1,3-dihydrofuro[3,4-c]pyridin-7-ol Chemical compound N1=C(CC=2C=CC=CC=2)C(O)=C2COCC2=C1CC1=CC=CC=C1 SDDLZCWMXNITJW-UHFFFAOYSA-N 0.000 description 2
- HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 2
- GECDGNKHVOETAA-UHFFFAOYSA-N 4-benzyl-6-ethyl-1,3-dihydrofuro[3,4-c]pyridin-7-ol Chemical compound C=12COCC2=C(O)C(CC)=NC=1CC1=CC=CC=C1 GECDGNKHVOETAA-UHFFFAOYSA-N 0.000 description 2
- XFSBVAOIAHNAPC-UHFFFAOYSA-N Aconitin Natural products CCN1CC(C(CC2OC)O)(COC)C3C(OC)C(C(C45)(OC(C)=O)C(O)C6OC)C1C32C4CC6(O)C5OC(=O)C1=CC=CC=C1 XFSBVAOIAHNAPC-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Natural products OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 230000007059 acute toxicity Effects 0.000 description 2
- 231100000403 acute toxicity Toxicity 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 150000004292 cyclic ethers Chemical class 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 2
- GFAZHVHNLUBROE-UHFFFAOYSA-N hydroxymethyl propionaldehyde Natural products CCC(=O)CO GFAZHVHNLUBROE-UHFFFAOYSA-N 0.000 description 2
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 2
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 2
- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 2
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 2
- 238000001802 infusion Methods 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 1
- MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 description 1
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- LJVHJHLTRBXGMH-HNQUOIGGSA-N (e)-1,4-dibromobut-1-ene Chemical compound BrCC\C=C\Br LJVHJHLTRBXGMH-HNQUOIGGSA-N 0.000 description 1
- LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
- C07D213/80—Acids; Esters in position 3
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61C—DENTISTRY; APPARATUS OR METHODS FOR ORAL OR DENTAL HYGIENE
- A61C8/00—Means to be fixed to the jaw-bone for consolidating natural teeth or for fixing dental prostheses thereon; Dental implants; Implanting tools
- A61C8/0018—Means to be fixed to the jaw-bone for consolidating natural teeth or for fixing dental prostheses thereon; Dental implants; Implanting tools characterised by the shape
-
- 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
-
- 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
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- 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
-
- 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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/65—One oxygen atom attached in position 3 or 5
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D263/32—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61C—DENTISTRY; APPARATUS OR METHODS FOR ORAL OR DENTAL HYGIENE
- A61C2204/00—Features not otherwise provided for
- A61C2204/002—Features not otherwise provided for using batteries
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Cardiology (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Heart & Thoracic Surgery (AREA)
- Dentistry (AREA)
- Oral & Maxillofacial Surgery (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Epidemiology (AREA)
- Hospice & Palliative Care (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pyridine Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
Priority Applications (32)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19772760038 DE2760038C2 (en, 2012) | 1977-03-17 | 1977-03-17 | |
DE19772711655 DE2711655A1 (de) | 1977-03-17 | 1977-03-17 | Pyridinyl-aminoalkylaether |
GR55546A GR64096B (en) | 1977-03-17 | 1978-02-25 | Aminoalkylethers of pyridinyl |
GB9334/78A GB1599061A (en) | 1977-03-17 | 1978-03-09 | Pyridinyl aminoalkyl ethers useful for treating cardiac arrhythmias |
IT21099/78A IT1093796B (it) | 1977-03-17 | 1978-03-10 | Piridinil-aminoalchileteri |
US05/885,434 US4206117A (en) | 1977-03-17 | 1978-03-10 | Pyridinyl aminoalkyl ethers |
IL54265A IL54265A0 (en) | 1977-03-17 | 1978-03-13 | New pyrimidinyl aminoalkyl ether derivatives, their manufacture and pharmaceutical compositions containing them |
NLAANVRAGE7802719,A NL189563C (nl) | 1977-03-17 | 1978-03-13 | Pyridyl-aminoalkyl-ethers alsmede farmaceutische preparaten daarvan die werkzaam zijn tegen hartritmestoornissen. |
IE503/78A IE46484B1 (en) | 1977-03-17 | 1978-03-13 | Pyridinyl aminoalkyl ehers useful for treating cardiac arrhythmias |
CH278478A CH638186A5 (de) | 1977-03-17 | 1978-03-14 | Neue pyridinyl-aminoalkylaether. |
SE7802927A SE446185B (sv) | 1977-03-17 | 1978-03-14 | Forfarande for framstellning av pyridinylaminoalkyletrar |
FR7807262A FR2383930A1 (fr) | 1977-03-17 | 1978-03-14 | Ethers aminoalcoyliques de pyridinyle, leurs procedes d'obtention et preparations pharmaceutiques les contenant |
LU79235A LU79235A1 (de) | 1977-03-17 | 1978-03-15 | Verfahren zur herstellung neuer pyridinyl-aminoalkylaethern |
DD78204190A DD134090A5 (de) | 1977-03-17 | 1978-03-15 | Verfahren zur herstellung von pyridinylaminoalkylaether |
SU782589450A SU799658A3 (ru) | 1977-03-17 | 1978-03-15 | Способ получени солей пири-диНилАМиНОАлКилОВыХ эфиРОВ |
BE185950A BE864917A (fr) | 1977-03-17 | 1978-03-15 | Ethers aminoalcoyliques de pyridinyle, procedes pour leur preparation et preparations pharmaceutiques les contenant |
AT0187878A AT364360B (de) | 1977-03-17 | 1978-03-16 | Verfahren zur herstellung von neuen pyridinyl-aminoalkylaethern und ihrer saeureadditionssalze |
NO780931A NO150605C (no) | 1977-03-17 | 1978-03-16 | Analogifremgangsmaate for fremstilling av terapeutisk aktive pyridinyl-aminoalkyletere |
ES467931A ES467931A1 (es) | 1977-03-17 | 1978-03-16 | Procedimiento para la obtencion de piridinil-aminoalquilete-res |
HU78BA3641A HU177287B (en) | 1977-03-17 | 1978-03-16 | Process for producing pyrimidyl-aminoalkylether derivatives |
AU34195/78A AU525566B2 (en) | 1977-03-01 | 1978-03-16 | Pyridinyl aminoalkyl ethers |
YU00636/78A YU63678A (en) | 1977-03-17 | 1978-03-16 | Process for obtaining new pyridinyl-aminoalkylethers |
CS787593A CS202012B2 (en) | 1977-03-17 | 1978-03-16 | Process for preparing new pyridylaminoalkylethers |
ZA00781552A ZA781552B (en) | 1977-03-17 | 1978-03-16 | Pyridinyl aminoalkyl ethers,their preparation and pharmaceutical formulations thereof |
CA299,068A CA1108148A (en) | 1977-03-17 | 1978-03-16 | Pyridinyl aminoalkyl ethers |
CS781680A CS202011B2 (en) | 1977-03-17 | 1978-03-16 | Process for preparing new pyridylaminoalkylethers |
DK118578A DK118578A (da) | 1977-03-17 | 1978-03-16 | Fr&mgangsmaade til fremstilling af pyridinylaminoalkylethere,n-oxider eller physiologisk acceptable syreadditionssalte deraf |
FI780842A FI74962C (fi) | 1977-03-17 | 1978-03-17 | Foerfarande foer framstaellning av terapeutiskt anvaendbara 4,5-dikarbalkoxi-6-bensylpyridin-3-yl- - alkylaminoalkyletrar och 4-bensyl-1,3-dihydrofuro/3,4-c/pyridin-7-yl- alkylaminoalkyletrar. |
JP3004178A JPS53116382A (en) | 1977-03-17 | 1978-03-17 | Novel pyridinyllaminoalkyl ether |
SU782699099A SU850002A3 (ru) | 1977-03-17 | 1978-12-19 | Способ получени простых пиридиниламино-АлКилОВыХ эфиРОВ или иХ физиОлОгичЕСКипРиЕМлЕМыХ СОлЕй |
AT0084080A AT364361B (de) | 1977-03-17 | 1980-02-15 | Verfahren zur herstellung von neuen pyridinyl-aminoalkylaethern und ihrer saeureadditionssalze |
YU2252/82A YU41016B (en) | 1977-03-17 | 1982-10-07 | Process for obtaining new pyridinyl aminoalkylethers |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19772711655 DE2711655A1 (de) | 1977-03-17 | 1977-03-17 | Pyridinyl-aminoalkylaether |
Publications (2)
Publication Number | Publication Date |
---|---|
DE2711655A1 DE2711655A1 (de) | 1978-09-21 |
DE2711655C2 true DE2711655C2 (en, 2012) | 1987-07-16 |
Family
ID=6003884
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE19772711655 Granted DE2711655A1 (de) | 1977-03-01 | 1977-03-17 | Pyridinyl-aminoalkylaether |
Country Status (27)
Country | Link |
---|---|
US (1) | US4206117A (en, 2012) |
JP (1) | JPS53116382A (en, 2012) |
AT (2) | AT364360B (en, 2012) |
AU (1) | AU525566B2 (en, 2012) |
BE (1) | BE864917A (en, 2012) |
CA (1) | CA1108148A (en, 2012) |
CH (1) | CH638186A5 (en, 2012) |
CS (2) | CS202012B2 (en, 2012) |
DD (1) | DD134090A5 (en, 2012) |
DE (1) | DE2711655A1 (en, 2012) |
DK (1) | DK118578A (en, 2012) |
ES (1) | ES467931A1 (en, 2012) |
FI (1) | FI74962C (en, 2012) |
FR (1) | FR2383930A1 (en, 2012) |
GB (1) | GB1599061A (en, 2012) |
GR (1) | GR64096B (en, 2012) |
HU (1) | HU177287B (en, 2012) |
IE (1) | IE46484B1 (en, 2012) |
IL (1) | IL54265A0 (en, 2012) |
IT (1) | IT1093796B (en, 2012) |
LU (1) | LU79235A1 (en, 2012) |
NL (1) | NL189563C (en, 2012) |
NO (1) | NO150605C (en, 2012) |
SE (1) | SE446185B (en, 2012) |
SU (2) | SU799658A3 (en, 2012) |
YU (2) | YU63678A (en, 2012) |
ZA (1) | ZA781552B (en, 2012) |
Families Citing this family (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4474781A (en) * | 1979-04-02 | 1984-10-02 | Merck & Co., Inc. | Treating hypertension with aminoalkoxypyridines |
DE3008522A1 (de) * | 1980-03-06 | 1981-09-17 | Basf Ag, 6700 Ludwigshafen | 4-(alpha)-cycloamino-arylmethyl-6-methyl-1,3-dihydro-furo (3,4-c) -pyridin-7-ole, ihre herstellung und verwendung |
IL62602A (en) * | 1980-05-19 | 1984-06-29 | Labaz Sanofi Nv | Pyridoxine derivatives,their preparation and pharmaceutical compositions containing them |
JPS588066A (ja) * | 1981-07-03 | 1983-01-18 | Otsuka Pharmaceut Co Ltd | 光学活性〔s〕−(−)−カルボスチリル誘導体の製造法 |
DE3373466D1 (de) * | 1982-06-10 | 1987-10-15 | Beecham Wuelfing Gmbh & Co Kg | Amine derivatives |
DE3519693A1 (de) * | 1985-06-01 | 1987-01-02 | Basf Ag | Pyridin-derivate, ihre herstellung und verwendung |
GB8603475D0 (en) * | 1986-02-12 | 1986-03-19 | Glaxo Group Ltd | Chemical compounds |
GB8703007D0 (en) * | 1987-02-10 | 1987-03-18 | Glaxo Group Ltd | Chemical compounds |
GB9012926D0 (en) * | 1990-06-09 | 1990-08-01 | Scras | Pyrrolo-pyridine derivatives |
CA2396738C (en) * | 1990-11-30 | 2006-08-29 | Masatoshi Chihiro | Thiazole derivatives as active superoxide radical inhibitors |
IL109104A (en) * | 1993-03-26 | 1998-08-16 | Shell Int Research | History of pyridine from wool - 2,6 Preparation and use as herbicides containing them |
MY128323A (en) | 1996-09-30 | 2007-01-31 | Otsuka Pharma Co Ltd | Thiazole derivatives for inhibition of cytokine production and of cell adhesion |
US20010034357A1 (en) * | 2000-02-02 | 2001-10-25 | Nan-Horng Lin | Substituted pyridine compounds useful for controlling chemical synaptic transmission |
CA2521135A1 (en) * | 2003-04-07 | 2004-10-28 | Kalypsys, Inc. | N-containing heteroaromatic compounds as modulators of ppars and methods of treating metabolic disorders |
SMT202000257T1 (it) * | 2008-10-10 | 2020-07-08 | Vm Discovery Inc | Composizioni e metodi per il trattamento dei disturbi da uso di alcol, dolore e altre malattie |
KR101698153B1 (ko) * | 2010-04-26 | 2017-01-23 | 광주과학기술원 | P2x1 및 p2x3 수용체 길항제로 사용되는 신규한 피리딘 카르복실산계 화합물, 이의 제조방법 및 이를 포함하는 조성물 |
Family Cites Families (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US1572768A (en) * | 1925-06-26 | 1926-02-09 | Winthrop Chem Co Inc | Pharmaceutical product |
US1881236A (en) * | 1929-08-10 | 1932-10-04 | Soc Of Chemical Ind | Basic ethers of the pyridine series |
US3535328A (en) * | 1967-09-01 | 1970-10-20 | Exxon Research Engineering Co | Certain substituted aminothioethoxy pyridines |
AR208397A1 (es) * | 1973-02-20 | 1976-12-27 | Ciba Geigy Ag | Procedimiento para la elaboracion de compuestos de 1-piridiloxi-2-hidroxi-3-amino-propano1-piraziniloxi-2-hidroxi-3-amino-propano y 1-pirimidiniloxi-2-hidroxi-3-amino-propan |
US4115575A (en) * | 1973-02-20 | 1978-09-19 | Ciba-Geigy Corporation | 2-(3-Amino-2-hydroxy-propoxy)-pyrazines |
US4073909A (en) * | 1973-10-08 | 1978-02-14 | Sandoz Ltd. | Isoquinoline compounds |
CH591448A5 (en, 2012) * | 1974-05-14 | 1977-09-15 | Ciba Geigy Ag | |
CH614711A5 (en, 2012) * | 1975-04-08 | 1979-12-14 | Sandoz Ag | |
GB1504424A (en) * | 1975-08-09 | 1978-03-22 | Beecham Group Ltd | Isoquinoline-derived aminoethers |
GB1485919A (en) * | 1975-08-12 | 1977-09-14 | Grindstedvaerket As | Pyridine derivatives |
US4060601A (en) * | 1976-06-15 | 1977-11-29 | Merck & Co., Inc. | Certain lower-alkyl amino-2'-hydroxy-propoxy pyridines |
-
1977
- 1977-03-17 DE DE19772711655 patent/DE2711655A1/de active Granted
-
1978
- 1978-02-25 GR GR55546A patent/GR64096B/el unknown
- 1978-03-09 GB GB9334/78A patent/GB1599061A/en not_active Expired
- 1978-03-10 US US05/885,434 patent/US4206117A/en not_active Expired - Lifetime
- 1978-03-10 IT IT21099/78A patent/IT1093796B/it active
- 1978-03-13 IL IL54265A patent/IL54265A0/xx not_active IP Right Cessation
- 1978-03-13 IE IE503/78A patent/IE46484B1/en unknown
- 1978-03-13 NL NLAANVRAGE7802719,A patent/NL189563C/xx not_active IP Right Cessation
- 1978-03-14 SE SE7802927A patent/SE446185B/sv not_active IP Right Cessation
- 1978-03-14 CH CH278478A patent/CH638186A5/de not_active IP Right Cessation
- 1978-03-14 FR FR7807262A patent/FR2383930A1/fr active Granted
- 1978-03-15 BE BE185950A patent/BE864917A/xx not_active IP Right Cessation
- 1978-03-15 LU LU79235A patent/LU79235A1/de unknown
- 1978-03-15 DD DD78204190A patent/DD134090A5/xx unknown
- 1978-03-15 SU SU782589450A patent/SU799658A3/ru active
- 1978-03-16 HU HU78BA3641A patent/HU177287B/hu not_active IP Right Cessation
- 1978-03-16 CS CS787593A patent/CS202012B2/cs unknown
- 1978-03-16 CA CA299,068A patent/CA1108148A/en not_active Expired
- 1978-03-16 AU AU34195/78A patent/AU525566B2/en not_active Expired
- 1978-03-16 DK DK118578A patent/DK118578A/da unknown
- 1978-03-16 YU YU00636/78A patent/YU63678A/xx unknown
- 1978-03-16 AT AT0187878A patent/AT364360B/de not_active IP Right Cessation
- 1978-03-16 ES ES467931A patent/ES467931A1/es not_active Expired
- 1978-03-16 CS CS781680A patent/CS202011B2/cs unknown
- 1978-03-16 NO NO780931A patent/NO150605C/no unknown
- 1978-03-16 ZA ZA00781552A patent/ZA781552B/xx unknown
- 1978-03-17 FI FI780842A patent/FI74962C/fi not_active IP Right Cessation
- 1978-03-17 JP JP3004178A patent/JPS53116382A/ja active Granted
- 1978-12-19 SU SU782699099A patent/SU850002A3/ru active
-
1980
- 1980-02-15 AT AT0084080A patent/AT364361B/de not_active IP Right Cessation
-
1982
- 1982-10-07 YU YU2252/82A patent/YU41016B/xx unknown
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