CA1094088A - Heterocyclic amino-alcohol derivatives and their preparation - Google Patents

Heterocyclic amino-alcohol derivatives and their preparation

Info

Publication number: CA1094088A
Authority: CA; Canada
Prior art keywords: radical; alkyl; hydrogen; substituted; phenyl
Prior art date: 1975-11-18
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

CA266,041A

Other languages

English (en)

French (fr)

Inventor

Georges Lambelin

Joseph Roba

Claude Gillet

Romeo Roncucci

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.)

Continental Pharma Inc

Original Assignee

Continental Pharma Inc

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.)

1975-11-18

Filing date

1976-11-18

Publication date

1981-01-20

1976-11-18 Application filed by Continental Pharma Inc filed Critical Continental Pharma Inc

1981-01-20 Application granted granted Critical

1981-01-20 Publication of CA1094088A publication Critical patent/CA1094088A/en

Status Expired legal-status Critical Current

Links

-1 Heterocyclic amino-alcohol derivatives Chemical class 0.000 title claims abstract description 129
238000002360 preparation method Methods 0.000 title description 6
150000003254 radicals Chemical class 0.000 claims abstract description 146
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 76
239000001257 hydrogen Substances 0.000 claims abstract description 73
125000000217 alkyl group Chemical group 0.000 claims abstract description 72
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 35
229910052717 sulfur Inorganic materials 0.000 claims abstract description 34
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 28
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 25
229910052760 oxygen Inorganic materials 0.000 claims abstract description 25
239000011593 sulfur Chemical group 0.000 claims abstract description 25
125000001589 carboacyl group Chemical group 0.000 claims abstract description 24
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 24
239000001301 oxygen Substances 0.000 claims abstract description 24
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims abstract description 22
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims abstract description 21
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 20
150000001414 amino alcohols Chemical class 0.000 claims abstract description 13
125000005843 halogen group Chemical group 0.000 claims abstract description 11
125000003545 alkoxy group Chemical group 0.000 claims abstract description 10
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 10
GLUUGHFHXGJENI-UHFFFAOYSA-N diethylenediamine Natural products C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims abstract description 9
125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 9
NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims abstract description 8
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims abstract description 6
125000003342 alkenyl group Polymers 0.000 claims abstract description 6
150000002825 nitriles Chemical class 0.000 claims abstract description 6
125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 5
WZKSXHQDXQKIQJ-UHFFFAOYSA-N F[C](F)F Chemical compound F[C](F)F WZKSXHQDXQKIQJ-UHFFFAOYSA-N 0.000 claims abstract description 4
125000004442 acylamino group Chemical group 0.000 claims abstract description 4
125000005422 alkyl sulfonamido group Chemical group 0.000 claims abstract description 4
ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical compound O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims abstract description 4
HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims abstract description 4
125000004429 atom Chemical group 0.000 claims abstract description 3
YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical compound O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 claims abstract description 3
125000003884 phenylalkyl group Chemical group 0.000 claims abstract description 3
238000000034 method Methods 0.000 claims description 44
150000002431 hydrogen Chemical group 0.000 claims description 35
230000008569 process Effects 0.000 claims description 35
239000002904 solvent Substances 0.000 claims description 30
150000001875 compounds Chemical class 0.000 claims description 27
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 26
LEVJVKGPFAQPOI-UHFFFAOYSA-N phenylmethanone Chemical compound O=[C]C1=CC=CC=C1 LEVJVKGPFAQPOI-UHFFFAOYSA-N 0.000 claims description 21
150000003839 salts Chemical class 0.000 claims description 20
BDERNNFJNOPAEC-UHFFFAOYSA-N 1-propanol Substances CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 16
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 16
230000009467 reduction Effects 0.000 claims description 12
238000006722 reduction reaction Methods 0.000 claims description 12
239000002253 acid Substances 0.000 claims description 10
239000000460 chlorine Substances 0.000 claims description 10
229910052736 halogen Inorganic materials 0.000 claims description 10
150000002367 halogens Chemical class 0.000 claims description 10
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 9
KHUXNRRPPZOJPT-UHFFFAOYSA-N phenoxy radical Chemical compound O=C1C=C[CH]C=C1 KHUXNRRPPZOJPT-UHFFFAOYSA-N 0.000 claims description 8
150000001412 amines Chemical class 0.000 claims description 7
238000006243 chemical reaction Methods 0.000 claims description 7
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 6
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 5
125000000304 alkynyl group Chemical group 0.000 claims description 5
150000008064 anhydrides Chemical class 0.000 claims description 5
239000002585 base Substances 0.000 claims description 5
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
BNJMRELGMDUDDB-UHFFFAOYSA-N $l^{1}-sulfanylbenzene Chemical compound [S]C1=CC=CC=C1 BNJMRELGMDUDDB-UHFFFAOYSA-N 0.000 claims description 4
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 4
229910052782 aluminium Inorganic materials 0.000 claims description 4
229910052801 chlorine Inorganic materials 0.000 claims description 4
125000000753 cycloalkyl group Chemical group 0.000 claims description 4
150000007522 mineralic acids Chemical class 0.000 claims description 4
239000000126 substance Substances 0.000 claims description 4
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 4
229910000102 alkali metal hydride Inorganic materials 0.000 claims description 3
150000008046 alkali metal hydrides Chemical class 0.000 claims description 3
AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 claims description 3
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 3
230000007062 hydrolysis Effects 0.000 claims description 3
238000006460 hydrolysis reaction Methods 0.000 claims description 3
150000007524 organic acids Chemical class 0.000 claims description 3
125000006239 protecting group Chemical group 0.000 claims description 3
OCUCCJIRFHNWBP-IYEMJOQQSA-L Copper gluconate Chemical class [Cu+2].OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O OCUCCJIRFHNWBP-IYEMJOQQSA-L 0.000 claims description 2
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 2
229910019142 PO4 Inorganic materials 0.000 claims description 2
150000001242 acetic acid derivatives Chemical class 0.000 claims description 2
150000001298 alcohols Chemical class 0.000 claims description 2
125000004414 alkyl thio group Chemical group 0.000 claims description 2
239000003054 catalyst Substances 0.000 claims description 2
150000001860 citric acid derivatives Chemical class 0.000 claims description 2
125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 2
150000003840 hydrochlorides Chemical class 0.000 claims description 2
238000005984 hydrogenation reaction Methods 0.000 claims description 2
150000003893 lactate salts Chemical class 0.000 claims description 2
238000006386 neutralization reaction Methods 0.000 claims description 2
150000003891 oxalate salts Chemical class 0.000 claims description 2
125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
235000021317 phosphate Nutrition 0.000 claims description 2
150000003013 phosphoric acid derivatives Chemical class 0.000 claims description 2
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 2
150000003467 sulfuric acid derivatives Chemical class 0.000 claims description 2
125000004434 sulfur atom Chemical group 0.000 claims 9
125000004430 oxygen atom Chemical group O* 0.000 claims 4
229910052731 fluorine Inorganic materials 0.000 claims 3
238000004519 manufacturing process Methods 0.000 claims 3
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims 2
125000001153 fluoro group Chemical group F* 0.000 claims 2
241000352333 Amegilla alpha Species 0.000 claims 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical class O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims 1
OMFRMAHOUUJSGP-IRHGGOMRSA-N bifenthrin Chemical compound C1=CC=C(C=2C=CC=CC=2)C(C)=C1COC(=O)[C@@H]1[C@H](\C=C(/Cl)C(F)(F)F)C1(C)C OMFRMAHOUUJSGP-IRHGGOMRSA-N 0.000 claims 1
239000011737 fluorine Substances 0.000 claims 1
239000012433 hydrogen halide Substances 0.000 claims 1
229910000039 hydrogen halide Inorganic materials 0.000 claims 1
125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
238000001556 precipitation Methods 0.000 claims 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 51
239000000047 product Substances 0.000 description 42
239000000203 mixture Substances 0.000 description 35
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 28
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 24
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 20
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
239000012074 organic phase Substances 0.000 description 19
238000007792 addition Methods 0.000 description 17
238000004458 analytical method Methods 0.000 description 17
229960005335 propanol Drugs 0.000 description 17
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 16
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
229910000033 sodium borohydride Inorganic materials 0.000 description 13
239000012279 sodium borohydride Substances 0.000 description 13
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 12
229910052794 bromium Inorganic materials 0.000 description 12
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 12
UKDOTCFNLHHKOF-FGRDZWBJSA-N (z)-1-chloroprop-1-ene;(z)-1,2-dichloroethene Chemical group C\C=C/Cl.Cl\C=C/Cl UKDOTCFNLHHKOF-FGRDZWBJSA-N 0.000 description 11
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 11
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 11
235000019441 ethanol Nutrition 0.000 description 11
238000003756 stirring Methods 0.000 description 11
230000000694 effects Effects 0.000 description 10
229910052943 magnesium sulfate Inorganic materials 0.000 description 10
RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 10
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 9
XQYZDYMELSJDRZ-UHFFFAOYSA-N papaverine Chemical compound C1=C(OC)C(OC)=CC=C1CC1=NC=CC2=CC(OC)=C(OC)C=C12 XQYZDYMELSJDRZ-UHFFFAOYSA-N 0.000 description 9
229940044613 1-propanol Drugs 0.000 description 8
229960004756 ethanol Drugs 0.000 description 8
238000002329 infrared spectrum Methods 0.000 description 8
235000019341 magnesium sulphate Nutrition 0.000 description 8
229910002012 Aerosil® Inorganic materials 0.000 description 7
229920002261 Corn starch Polymers 0.000 description 7
239000008120 corn starch Substances 0.000 description 7
238000002844 melting Methods 0.000 description 7
230000008018 melting Effects 0.000 description 7
AGNFWIZBEATIAK-UHFFFAOYSA-N 4-phenylbutylamine Chemical compound NCCCCC1=CC=CC=C1 AGNFWIZBEATIAK-UHFFFAOYSA-N 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
235000011167 hydrochloric acid Nutrition 0.000 description 6
229960000443 hydrochloric acid Drugs 0.000 description 6
238000001819 mass spectrum Methods 0.000 description 6
239000003208 petroleum Substances 0.000 description 6
229910052770 Uranium Inorganic materials 0.000 description 5
229940063656 aluminum chloride Drugs 0.000 description 5
229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
239000007787 solid Substances 0.000 description 5
IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 4
229930008281 A03AD01 - Papaverine Natural products 0.000 description 4
229920000168 Microcrystalline cellulose Polymers 0.000 description 4
235000019483 Peanut oil Nutrition 0.000 description 4
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 4
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 4
DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 4
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
150000007513 acids Chemical class 0.000 description 4
230000003276 anti-hypertensive effect Effects 0.000 description 4
239000008346 aqueous phase Substances 0.000 description 4
230000008570 general process Effects 0.000 description 4
239000000787 lecithin Substances 0.000 description 4
235000010445 lecithin Nutrition 0.000 description 4
229940067606 lecithin Drugs 0.000 description 4
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
235000019813 microcrystalline cellulose Nutrition 0.000 description 4
239000008108 microcrystalline cellulose Substances 0.000 description 4
229940016286 microcrystalline cellulose Drugs 0.000 description 4
239000003921 oil Substances 0.000 description 4
235000019198 oils Nutrition 0.000 description 4
229960001789 papaverine Drugs 0.000 description 4
239000000312 peanut oil Substances 0.000 description 4
238000010992 reflux Methods 0.000 description 4
239000001632 sodium acetate Substances 0.000 description 4
235000017281 sodium acetate Nutrition 0.000 description 4
235000017557 sodium bicarbonate Nutrition 0.000 description 4
235000019333 sodium laurylsulphate Nutrition 0.000 description 4
238000004809 thin layer chromatography Methods 0.000 description 4
VMZUJJGAJWYSBO-UHFFFAOYSA-N 1-(3,4-dihydro-2h-thiochromen-6-yl)propan-1-one Chemical compound S1CCCC2=CC(C(=O)CC)=CC=C21 VMZUJJGAJWYSBO-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
229920003091 Methocel™ Polymers 0.000 description 3
235000010210 aluminium Nutrition 0.000 description 3
239000002775 capsule Substances 0.000 description 3
230000000875 corresponding effect Effects 0.000 description 3
239000012467 final product Substances 0.000 description 3
229960004592 isopropanol Drugs 0.000 description 3
229960005141 piperazine Drugs 0.000 description 3
238000001953 recrystallisation Methods 0.000 description 3
CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
BISQTCXKVNCDDA-UHFFFAOYSA-N thiepine Chemical compound S1C=CC=CC=C1 BISQTCXKVNCDDA-UHFFFAOYSA-N 0.000 description 3
229940015849 thiophene Drugs 0.000 description 3
URIOMIMEFWTNPP-UHFFFAOYSA-N 1-(2-methyl-3,4-dihydro-2h-thiochromen-6-yl)-2-(4-phenylbutylamino)propan-1-ol Chemical compound C=1C=C2SC(C)CCC2=CC=1C(O)C(C)NCCCCC1=CC=CC=C1 URIOMIMEFWTNPP-UHFFFAOYSA-N 0.000 description 2
JWBXDPNEGMODGZ-UHFFFAOYSA-N 1-(3,4-dihydro-2h-thiochromen-6-yl)-2-(4-phenylbutylamino)propan-1-ol Chemical compound C=1C=C2SCCCC2=CC=1C(O)C(C)NCCCCC1=CC=CC=C1 JWBXDPNEGMODGZ-UHFFFAOYSA-N 0.000 description 2
WPWNEKFMGCWNPR-UHFFFAOYSA-N 3,4-dihydro-2h-thiochromene Chemical compound C1=CC=C2CCCSC2=C1 WPWNEKFMGCWNPR-UHFFFAOYSA-N 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
238000005481 NMR spectroscopy Methods 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
208000005392 Spasm Diseases 0.000 description 2
229920002472 Starch Polymers 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
238000013019 agitation Methods 0.000 description 2
230000002921 anti-spasmodic effect Effects 0.000 description 2
230000002785 anti-thrombosis Effects 0.000 description 2
WDIHJSXYQDMJHN-UHFFFAOYSA-L barium chloride Chemical compound [Cl-].[Cl-].[Ba+2] WDIHJSXYQDMJHN-UHFFFAOYSA-L 0.000 description 2
229910001626 barium chloride Inorganic materials 0.000 description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
210000003169 central nervous system Anatomy 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
238000000605 extraction Methods 0.000 description 2
239000012530 fluid Substances 0.000 description 2
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 2
239000012458 free base Substances 0.000 description 2
238000007327 hydrogenolysis reaction Methods 0.000 description 2
230000000055 hyoplipidemic effect Effects 0.000 description 2
230000002401 inhibitory effect Effects 0.000 description 2
SIAPCJWMELPYOE-UHFFFAOYSA-N lithium hydride Chemical compound [LiH] SIAPCJWMELPYOE-UHFFFAOYSA-N 0.000 description 2
229910000103 lithium hydride Inorganic materials 0.000 description 2
235000019359 magnesium stearate Nutrition 0.000 description 2
235000005985 organic acids Nutrition 0.000 description 2
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- 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
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
- 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
- A61P9/08—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
- A61P9/12—Antihypertensives
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/10—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms
- C07D211/14—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms with hydrocarbon or substituted hydrocarbon radicals attached to the ring nitrogen atom
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
- C07D265/34—1,4-Oxazines; Hydrogenated 1,4-oxazines condensed with carbocyclic rings
- C07D265/36—1,4-Oxazines; Hydrogenated 1,4-oxazines condensed with carbocyclic rings condensed with one six-membered ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D327/00—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms
- C07D327/02—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms one oxygen atom and one sulfur atom
- C07D327/06—Six-membered rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/54—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D335/00—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom
- C07D335/04—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D335/06—Benzothiopyrans; Hydrogenated benzothiopyrans
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D337/00—Heterocyclic compounds containing rings of more than six members having one sulfur atom as the only ring hetero atom
- C07D337/02—Seven-membered rings
- C07D337/06—Seven-membered rings condensed with carbocyclic rings or ring systems
- C07D337/08—Seven-membered rings condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D339/00—Heterocyclic compounds containing rings having two sulfur atoms as the only ring hetero atoms
- C07D339/08—Six-membered rings

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Pharmacology & Pharmacy (AREA)
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Psychiatry (AREA)
Biomedical Technology (AREA)
Hematology (AREA)
Neurosurgery (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Plural Heterocyclic Compounds (AREA)
Hydrogenated Pyridines (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Heterocyclic Compounds Containing Sulfur Atoms (AREA)

CA266,041A 1975-11-18 1976-11-18 Heterocyclic amino-alcohol derivatives and their preparation Expired CA1094088A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
FR7535217A FR2332010A1 (fr)	1975-11-18	1975-11-18	Amino-alcool heterocyclique, son sel et son procede de preparation
FR75.35217		1975-11-18

Publications (1)

Publication Number	Publication Date
CA1094088A true CA1094088A (en)	1981-01-20

Family

ID=9162563

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA266,041A Expired CA1094088A (en)	1975-11-18	1976-11-18	Heterocyclic amino-alcohol derivatives and their preparation

Country Status (21)

Country	Link
JP (2)	JPS5297952A (2)
AT (1)	AT355566B (2)
AU (1)	AU510315B2 (2)
BE (1)	BE848496A (2)
CA (1)	CA1094088A (2)
CH (2)	CH623321A5 (2)
DE (1)	DE2651572C2 (2)
DK (1)	DK151330C (2)
ES (1)	ES453389A1 (2)
FI (1)	FI763265A7 (2)
FR (1)	FR2332010A1 (2)
GB (1)	GB1565080A (2)
GR (1)	GR62012B (2)
IE (1)	IE44265B1 (2)
IL (1)	IL50932A (2)
MX (1)	MX4881E (2)
NL (1)	NL180936C (2)
NZ (1)	NZ182665A (2)
PT (1)	PT65853B (2)
SE (1)	SE434744B (2)
ZA (1)	ZA766907B (2)

Families Citing this family (22)

* Cited by examiner, † Cited by third party
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FR2512817A1 (fr) *	1981-09-17	1983-03-18	Roussel Uclaf	Nouveaux derives de l'aminomethyl 1h-indole-4-methanol et leurs sels, leur procede de preparation, leur application a titre de medicaments, les compositions les renfermant et leurs intermediaires de preparation
US4521606A (en) *	1983-06-30	1985-06-04	American Home Products Corp.	5-Indolyl substituted aminoethanols
US4622399A (en) *	1983-06-30	1986-11-11	American Home Products Corporation	Bicyclo-heterocyclic nitrogen substituted aminoethanol derivatives
US4562200A (en) *	1983-06-30	1985-12-31	American Home Products Corporation	5(Indolyl) and 5(2,3-dihydroindolyl) substituted aminoethanols and their use as anti-hypertensives
ATE194982T1 (de)	1992-04-24	2000-08-15	Takeda Chemical Industries Ltd	Benzoxazepin-derivate als cholinesterase- inhibitoren
US5705515A (en) *	1994-04-26	1998-01-06	Merck & Co., Inc.	Substituted sulfonamides as selective β-3 agonists for the treatment of diabetes and obesity
US5561142A (en) *	1994-04-26	1996-10-01	Merck & Co., Inc.	Substituted sulfonamides as selective β3 agonists for the treatment of diabetes and obesity
US5541197A (en) *	1994-04-26	1996-07-30	Merck & Co., Inc.	Substituted sulfonamides as selective β3 agonists for the treatment of diabetes and obesity
US5674891A (en) *	1994-07-27	1997-10-07	The Procter & Gamble Company	Dihydrobenzothiophene compounds useful as anti-inflammatory agents
US5684002A (en) *	1994-09-07	1997-11-04	The Procter & Gamble Company	Dihydorbenzofuran and related compounds useful as anti-inflammatory agents
JP3124242B2 (ja)	1996-01-10	2001-01-15	旭化成工業株式会社	新規な３環性化合物
ATE251608T1 (de)	1996-01-10	2003-10-15	Asahi Chemical Ind	Neue trizyklische verbindungen und arzneimittelzusammensetzungen die diese enthalten
US5684031A (en) *	1996-02-01	1997-11-04	The Procter & Gamble Company	Dihydrobenzofuran and related compounds useful as anti-inflammatory agents
US5672620A (en) *	1996-02-01	1997-09-30	The Procter & Gamble Company	Dihydrobenzofuran and related compounds useful as anti-inflammatory agents
WO1998033793A1 (fr) *	1997-01-30	1998-08-06	Sanofi-Synthelabo	DERIVES DE α-AZACYCLOMETHYL BENZOTHIOPHENE ET DE α-AZACYCLOMETHYL BENZOFURANE, LEUR PREPARATION ET LEUR APPLICATION EN THERAPEUTIQUE
FR2758820B1 (fr) *	1997-01-30	1999-02-26	Synthelabo	Derives de alpha-azacyclomethyl-benzofurane, leur preparation et leur application en therapeutique
US6172099B1 (en)	1997-07-03	2001-01-09	Asahi Kasei Kogyo Kabushiki Kaisha	Tricyclic compounds having saturated rings and medicinal compositions containing the same
PT1277736E (pt)	2000-04-28	2007-10-12	Asahi Kasei Pharma Corp	Novos compostos bicíclicos
EP1447400B1 (en)	2001-10-25	2008-09-17	Asahi Kasei Pharma Corporation	Bicyclic compound
USD529397S1 (en)	2004-08-18	2006-10-03	Gabrielle Studio, Inc.	Cosmetic container
JPWO2010041569A1 (ja)	2008-10-09	2012-03-08	旭化成ファーマ株式会社	インダゾール化合物
EP2351742A4 (en)	2008-10-09	2012-03-28	Asahi Kasei Pharma Corp	indazole

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1013224A (en) *	1962-06-21	1965-12-15	Ici Ltd	Heterocyclic aminoethanols
US3255249A (en) *	1963-04-26	1966-06-07	Ici Ltd	2-branched lower alkyl-amino-1-(indan-, hydrogenated indan- and hydrogenated naphth-2-yl) lower alkanols
CH442302A (de) *	1964-04-17	1967-08-31	Sandoz Ag	Verfahren zur Herstellung eines neuen Indolderivates
FR2138488A1 (en) *	1971-05-27	1973-01-05	Lipha	1-(5-indanyl)-omega-aminoalkanes - with tranquillizing activity

1975
- 1975-11-18 FR FR7535217A patent/FR2332010A1/fr active Granted
1976
- 1976-11-11 SE SE7612554A patent/SE434744B/xx not_active IP Right Cessation
- 1976-11-12 DE DE2651572A patent/DE2651572C2/de not_active Expired
- 1976-11-15 FI FI763265A patent/FI763265A7/fi not_active Application Discontinuation
- 1976-11-17 DK DK517076A patent/DK151330C/da not_active IP Right Cessation
- 1976-11-17 PT PT65853A patent/PT65853B/pt unknown
- 1976-11-17 ES ES453389A patent/ES453389A1/es not_active Expired
- 1976-11-17 NL NLAANVRAGE7612794,A patent/NL180936C/xx not_active IP Right Cessation
- 1976-11-17 AT AT854376A patent/AT355566B/de not_active IP Right Cessation
- 1976-11-17 IL IL50932A patent/IL50932A/xx unknown
- 1976-11-17 MX MX765135U patent/MX4881E/es unknown
- 1976-11-18 GB GB48127/76A patent/GB1565080A/en not_active Expired
- 1976-11-18 CH CH1454276A patent/CH623321A5/fr not_active IP Right Cessation
- 1976-11-18 JP JP13785976A patent/JPS5297952A/ja active Granted
- 1976-11-18 BE BE172486A patent/BE848496A/xx not_active IP Right Cessation
- 1976-11-18 NZ NZ182665A patent/NZ182665A/xx unknown
- 1976-11-18 AU AU19779/76A patent/AU510315B2/en not_active Expired
- 1976-11-18 CA CA266,041A patent/CA1094088A/en not_active Expired
- 1976-11-18 IE IE2541/76A patent/IE44265B1/en unknown
- 1976-11-18 GR GR52209A patent/GR62012B/el unknown
- 1976-11-18 ZA ZA766907A patent/ZA766907B/xx unknown
1980
- 1980-03-03 CH CH167280A patent/CH622770A5/fr not_active IP Right Cessation
1982
- 1982-01-12 JP JP57002388A patent/JPS6017778B2/ja not_active Expired

Also Published As

Publication number	Publication date
IE44265B1 (en)	1981-09-23
DE2651572C2 (de)	1982-05-19
NL7612794A (nl)	1977-05-23
FI763265A7 (2)	1977-05-19
ZA766907B (en)	1977-10-26
IL50932A (en)	1984-01-31
ES453389A1 (es)	1977-11-16
JPS63435B2 (2)	1988-01-07
FR2332010A1 (fr)	1977-06-17
GB1565080A (en)	1980-04-16
ATA854376A (de)	1979-08-15
DK151330B (da)	1987-11-23
CH622770A5 (en)	1981-04-30
NL180936B (nl)	1986-12-16
AT355566B (de)	1980-03-10
GR62012B (en)	1979-02-15
CH623321A5 (en)	1981-05-29
NL180936C (nl)	1987-05-18
SE434744B (sv)	1984-08-13
AU1977976A (en)	1978-05-25
DK517076A (da)	1977-05-19
PT65853B (fr)	1978-05-15
NZ182665A (en)	1978-11-13
IL50932A0 (en)	1977-01-31
IE44265L (en)	1977-05-18
JPS5297952A (en)	1977-08-17
JPS6017778B2 (ja)	1985-05-07
FR2332010B1 (2)	1979-06-29
AU510315B2 (en)	1980-06-19
MX4881E (es)	1982-11-30
DE2651572A1 (de)	1977-06-08
JPS57145843A (en)	1982-09-09
DK151330C (da)	1988-04-25
BE848496A (fr)	1977-05-18
SE7612554L (sv)	1977-05-19
PT65853A (fr)	1976-12-01

Legal Events

Date	Code	Title	Description
1998-01-20	MKEX	Expiry

Publication	Publication Date	Title
CA1136634A (en)	1982-11-30	Process for production of imidazole derivatives
US5145865A (en)	1992-09-08	Phenylcarboxylic acid derivatives having hetero ring
PL141830B1 (en)	1987-08-31	Method of obtaining novel derivatives of dihydropyridine
WO1991009013A1 (en)	1991-06-27	Muscarinic receptor antagonists
GB1565080A (en)	1980-04-16	Amino-alcohol derivatives and their preparation
CA2207429A1 (en)	1996-06-20	Polyarylcarbamoylaza - and - carbamoylalkanedioic acids
NO171060B (no)	1992-10-12	Analogifremgangsmaate for fremstilling av terapeutisk aktive n-cykloalkylalkyl-benzylaminer
KR900006721B1 (ko)	1990-09-20	2,6-피페리딘디온 유도체의 제조방법
NZ229865A (en)	1991-01-29	3-(optionally substituted)hydroxy-n-substituted piperidine derivatives and pharmaceutical compositions
US5166181A (en)	1992-11-24	Halogenoalkylphenyl-alcohols, ketones and hydrates thereof
US4638070A (en)	1987-01-20	Heterocyclic amino-alcohol derivatives
EP0326106B1 (en)	1994-07-27	Alkylene diamines
Girotra et al.	1992	Development, synthesis, and biological evaluation of (-)-trans-(2S, 5S)-2-[3-[(2-oxopropyl) sulfonyl]-4-n-propoxy-5-(3-hydroxypropoxy)-phenyl]-5-(3, 4, 5-trimethoxyphenyl) tetrahydrofuran, a potent orally active platelet-activating factor (PAF) antagonist and its water-soluble prodrug phosphate ester
WO2020140956A1 (en)	2020-07-09	Process for preparing sulfonamide compounds
FI71936B (fi)	1986-11-28	Foerfarande foer framstaellning av neuroleptiskt aktiva 2-substituerade-8-fluor-5-(4-fluorfenyl)-2,3,4,4a 5,9b-hexahydro-4a 9b-trans-1h-pyrido/4,3-b/indolderivat
IE893151L (en)	1990-04-04	Muscarinic receptor antagonists
AU662440B2 (en)	1995-08-31	Substituted acetamide derivatives
HU208970B (en)	1994-02-28	Process for producing new thienloxyalkyl derivatives and pharmaceutical compositions comprising same
Chiron et al.	2003	Synthesis and crystallographic studies of new acridinic esters and amides: An efficient synthetic route to 4-methyl functionalized acridines
HU194846B (en)	1988-03-28	Process for the production of derivatives of piperidine
PL84276B1 (2)	1976-03-31
PL111253B1 (en)	1980-08-30	Process for preparing novel derivatives of dibenzo/d,g//1,3,6/dioxazocin
MORIMOTO et al.	1978	Decarboxylation Reactions. IX. Reaction of Enamines with Trichloroacetic Anhydride
US6057454A (en)	2000-05-02	1-oxo-1H-inden-2-yl-1H-imidazole-2-carboxylic acid intermediates
CA1319145C (en)	1993-06-15	Substituted 3-piperidinamines or 3-azepinamines, the preparation thereof and their applications in therapy