NO874425L - Fremgangsmaate til fremstilling av (+)-1-isopropylamino-3-(o-pyrrol-l-yl)-fenoksy)-2-propanol og dets salter. - Google Patents

Fremgangsmaate til fremstilling av (+)-1-isopropylamino-3-(o-pyrrol-l-yl)-fenoksy)-2-propanol og dets salter.

Info

Publication number: NO874425L
Authority: NO; Norway
Prior art keywords: pyrrol; phenoxy; propanol; isopropylamino; enantiomer
Prior art date: 1986-10-24

Application number

NO874425A

Other languages

English (en)

Norwegian (no)

Other versions

NO874425D0 (no

Inventor

Franz Ostermayer

Joachim Jaekel

Nicole Veillon

Original Assignee

Ciba Geigy

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.)

1986-10-24

Filing date

1987-10-23

Publication date

1988-04-25

1986-10-24 Priority claimed from CH4235/86A external-priority patent/CH668185A5/de

1987-10-23 Application filed by Ciba Geigy filed Critical Ciba Geigy

1987-10-23 Publication of NO874425D0 publication Critical patent/NO874425D0/no

1988-04-25 Publication of NO874425L publication Critical patent/NO874425L/no

Links

KFZMGEQAYNKOFK-UHFFFAOYSA-N 2-propanol Substances CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 title claims description 30
238000000034 method Methods 0.000 title claims description 28
238000002360 preparation method Methods 0.000 title claims description 12
150000003839 salts Chemical class 0.000 claims description 44
239000013543 active substance Substances 0.000 claims description 31
-1 (+)-l-isopropylamino-[o-(pyrrol-l-yl)-phenoxy]-2-propanol Chemical compound 0.000 claims description 27
150000001875 compounds Chemical class 0.000 claims description 20
XVTVPGKWYHWYAD-UHFFFAOYSA-N 1-(propan-2-ylamino)-3-[2-(1-pyrrolyl)phenoxy]-2-propanol Chemical compound CC(C)NCC(O)COC1=CC=CC=C1N1C=CC=C1 XVTVPGKWYHWYAD-UHFFFAOYSA-N 0.000 claims description 19
238000004519 manufacturing process Methods 0.000 claims description 17
239000000825 pharmaceutical preparation Substances 0.000 claims description 17
208000019901 Anxiety disease Diseases 0.000 claims description 16
231100000252 nontoxic Toxicity 0.000 claims description 13
230000003000 nontoxic effect Effects 0.000 claims description 13
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
230000008569 process Effects 0.000 claims description 8
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 7
229910052736 halogen Inorganic materials 0.000 claims description 6
150000002367 halogens Chemical class 0.000 claims description 6
JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 claims description 6
239000000126 substance Substances 0.000 claims description 6
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 6
239000000969 carrier Substances 0.000 claims description 4
125000006239 protecting group Chemical group 0.000 claims description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 3
125000003277 amino group Chemical group 0.000 claims description 3
239000000546 pharmaceutical excipient Substances 0.000 claims description 2
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
230000000949 anxiolytic effect Effects 0.000 description 16
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
239000000203 mixture Substances 0.000 description 15
238000012360 testing method Methods 0.000 description 12
241000700159 Rattus Species 0.000 description 11
239000002585 base Substances 0.000 description 10
239000002253 acid Substances 0.000 description 9
239000002249 anxiolytic agent Substances 0.000 description 9
230000000694 effects Effects 0.000 description 9
241000282560 Macaca mulatta Species 0.000 description 8
230000001430 anti-depressive effect Effects 0.000 description 8
230000001777 nootropic effect Effects 0.000 description 8
241001465754 Metazoa Species 0.000 description 7
239000000935 antidepressant agent Substances 0.000 description 7
238000006243 chemical reaction Methods 0.000 description 7
238000000576 coating method Methods 0.000 description 7
230000007935 neutral effect Effects 0.000 description 7
235000011121 sodium hydroxide Nutrition 0.000 description 7
239000007858 starting material Substances 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
241000282693 Cercopithecidae Species 0.000 description 6
229940005513 antidepressants Drugs 0.000 description 6
239000003826 tablet Substances 0.000 description 6
IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 5
238000009472 formulation Methods 0.000 description 5
208000013403 hyperactivity Diseases 0.000 description 5
229920001223 polyethylene glycol Polymers 0.000 description 5
AQHHHDLHHXJYJD-UHFFFAOYSA-N propranolol Chemical compound C1=CC=C2C(OCC(O)CNC(C)C)=CC=CC2=C1 AQHHHDLHHXJYJD-UHFFFAOYSA-N 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
OCNROSNJUWZOCM-WLHGVMLRSA-N (e)-but-2-enedioic acid;1-(propan-2-ylamino)-3-(2-pyrrol-1-ylphenoxy)propan-2-ol Chemical compound OC(=O)\C=C\C(O)=O.CC(C)NCC(O)COC1=CC=CC=C1N1C=CC=C1 OCNROSNJUWZOCM-WLHGVMLRSA-N 0.000 description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
229920002472 Starch Polymers 0.000 description 4
238000010171 animal model Methods 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
230000000903 blocking effect Effects 0.000 description 4
239000002775 capsule Substances 0.000 description 4
239000011248 coating agent Substances 0.000 description 4
239000007941 film coated tablet Substances 0.000 description 4
230000035939 shock Effects 0.000 description 4
239000000243 solution Substances 0.000 description 4
239000002904 solvent Substances 0.000 description 4
235000019698 starch Nutrition 0.000 description 4
CEMAWMOMDPGJMB-UHFFFAOYSA-N (+-)-Oxprenolol Chemical compound CC(C)NCC(O)COC1=CC=CC=C1OCC=C CEMAWMOMDPGJMB-UHFFFAOYSA-N 0.000 description 3
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 3
FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 3
206010012289 Dementia Diseases 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
108010010803 Gelatin Proteins 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
230000009471 action Effects 0.000 description 3
239000001913 cellulose Substances 0.000 description 3
229920002678 cellulose Polymers 0.000 description 3
238000003776 cleavage reaction Methods 0.000 description 3
239000008298 dragée Substances 0.000 description 3
229920000159 gelatin Polymers 0.000 description 3
235000019322 gelatine Nutrition 0.000 description 3
235000011852 gelatine desserts Nutrition 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
230000005764 inhibitory process Effects 0.000 description 3
239000007788 liquid Substances 0.000 description 3
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Substances [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 3
230000003287 optical effect Effects 0.000 description 3
229960004570 oxprenolol Drugs 0.000 description 3
239000012188 paraffin wax Substances 0.000 description 3
238000007911 parenteral administration Methods 0.000 description 3
239000001267 polyvinylpyrrolidone Substances 0.000 description 3
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 3
229920000036 polyvinylpyrrolidone Polymers 0.000 description 3
230000009467 reduction Effects 0.000 description 3
230000007017 scission Effects 0.000 description 3
239000000600 sorbitol Substances 0.000 description 3
239000003381 stabilizer Substances 0.000 description 3
239000000829 suppository Substances 0.000 description 3
239000000725 suspension Substances 0.000 description 3
239000000454 talc Substances 0.000 description 3
229910052623 talc Inorganic materials 0.000 description 3
235000012222 talc Nutrition 0.000 description 3
150000003626 triacylglycerols Chemical class 0.000 description 3
HDPNBNXLBDFELL-UHFFFAOYSA-N 1,1,1-trimethoxyethane Chemical compound COC(C)(OC)OC HDPNBNXLBDFELL-UHFFFAOYSA-N 0.000 description 2
SGUVLZREKBPKCE-UHFFFAOYSA-N 1,5-diazabicyclo[4.3.0]-non-5-ene Chemical compound C1CCN=C2CCCN21 SGUVLZREKBPKCE-UHFFFAOYSA-N 0.000 description 2
RHXISQQDPMQSEB-LLVKDONJSA-N 1-[2-[[(2r)-oxiran-2-yl]methoxy]phenyl]pyrrole Chemical compound C([C@@H]1OC1)OC1=CC=CC=C1N1C=CC=C1 RHXISQQDPMQSEB-LLVKDONJSA-N 0.000 description 2
GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 2
NZABOAAWARHJSH-UHFFFAOYSA-N 2-pyrrol-1-ylphenol Chemical compound OC1=CC=CC=C1N1C=CC=C1 NZABOAAWARHJSH-UHFFFAOYSA-N 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
239000002202 Polyethylene glycol Substances 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
239000007868 Raney catalyst Substances 0.000 description 2
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 2
229910000564 Raney nickel Inorganic materials 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
206010041250 Social phobia Diseases 0.000 description 2
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 2
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
238000005903 acid hydrolysis reaction Methods 0.000 description 2
230000002730 additional effect Effects 0.000 description 2
UCTWMZQNUQWSLP-UHFFFAOYSA-N adrenaline Chemical compound CNCC(O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-UHFFFAOYSA-N 0.000 description 2
150000008044 alkali metal hydroxides Chemical class 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
239000011230 binding agent Substances 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
239000001506 calcium phosphate Substances 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
238000009903 catalytic hydrogenation reaction Methods 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 2
230000001684 chronic effect Effects 0.000 description 2
238000001816 cooling Methods 0.000 description 2
230000006735 deficit Effects 0.000 description 2
150000002009 diols Chemical class 0.000 description 2
238000001647 drug administration Methods 0.000 description 2
230000002526 effect on cardiovascular system Effects 0.000 description 2
239000010685 fatty oil Substances 0.000 description 2
239000000945 filler Substances 0.000 description 2
210000004051 gastric juice Anatomy 0.000 description 2
239000008273 gelatin Substances 0.000 description 2
239000008187 granular material Substances 0.000 description 2
229930195733 hydrocarbon Natural products 0.000 description 2
150000002430 hydrocarbons Chemical class 0.000 description 2
238000005984 hydrogenation reaction Methods 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
230000006872 improvement Effects 0.000 description 2
230000002401 inhibitory effect Effects 0.000 description 2
238000002347 injection Methods 0.000 description 2
239000007924 injection Substances 0.000 description 2
238000011835 investigation Methods 0.000 description 2
239000008101 lactose Substances 0.000 description 2
239000000314 lubricant Substances 0.000 description 2
235000019359 magnesium stearate Nutrition 0.000 description 2
239000000463 material Substances 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
229920000609 methyl cellulose Polymers 0.000 description 2
239000001923 methylcellulose Substances 0.000 description 2
235000010981 methylcellulose Nutrition 0.000 description 2
150000007522 mineralic acids Chemical class 0.000 description 2
230000008450 motivation Effects 0.000 description 2
239000002664 nootropic agent Substances 0.000 description 2
239000003921 oil Substances 0.000 description 2
235000019198 oils Nutrition 0.000 description 2
208000019906 panic disease Diseases 0.000 description 2
230000000737 periodic effect Effects 0.000 description 2
208000019899 phobic disease Diseases 0.000 description 2
XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 2
229940068196 placebo Drugs 0.000 description 2
239000000902 placebo Substances 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
239000011591 potassium Substances 0.000 description 2
230000003389 potentiating effect Effects 0.000 description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
238000012545 processing Methods 0.000 description 2
239000001294 propane Substances 0.000 description 2
239000012429 reaction media Substances 0.000 description 2
102000005962 receptors Human genes 0.000 description 2
108020003175 receptors Proteins 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
239000012312 sodium hydride Substances 0.000 description 2
229910000104 sodium hydride Inorganic materials 0.000 description 2
239000007787 solid Substances 0.000 description 2
239000008107 starch Substances 0.000 description 2
BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 2
238000003786 synthesis reaction Methods 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
238000012546 transfer Methods 0.000 description 2
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical class [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 2
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
239000002966 varnish Substances 0.000 description 2
XVTVPGKWYHWYAD-CQSZACIVSA-N (2r)-1-(propan-2-ylamino)-3-(2-pyrrol-1-ylphenoxy)propan-2-ol Chemical compound CC(C)NC[C@@H](O)COC1=CC=CC=C1N1C=CC=C1 XVTVPGKWYHWYAD-CQSZACIVSA-N 0.000 description 1
YJQIWIZKCMXILD-LLVKDONJSA-N (2r)-3-(2-pyrrol-1-ylphenoxy)propane-1,2-diol Chemical compound OC[C@@H](O)COC1=CC=CC=C1N1C=CC=C1 YJQIWIZKCMXILD-LLVKDONJSA-N 0.000 description 1
LNAZSHAWQACDHT-XIYTZBAFSA-N (2r,3r,4s,5r,6s)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2s,3r,4s,5r,6r)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6r)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 description 1
IWYDHOAUDWTVEP-SSDOTTSWSA-N (R)-mandelic acid Chemical compound OC(=O)[C@H](O)C1=CC=CC=C1 IWYDHOAUDWTVEP-SSDOTTSWSA-N 0.000 description 1
CTKINSOISVBQLD-VKHMYHEASA-N (S)-Glycidol Chemical compound OC[C@H]1CO1 CTKINSOISVBQLD-VKHMYHEASA-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
DCOXRJZVVPMXLY-UHFFFAOYSA-N 1-(propan-2-ylamino)-3-(2-pyrrol-1-ylphenoxy)propan-2-ol;hydrochloride Chemical compound Cl.CC(C)NCC(O)COC1=CC=CC=C1N1C=CC=C1 DCOXRJZVVPMXLY-UHFFFAOYSA-N 0.000 description 1
IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 description 1
HTWIZMNMTWYQRN-UHFFFAOYSA-N 2-methyl-1,3-dioxolane Chemical compound CC1OCCO1 HTWIZMNMTWYQRN-UHFFFAOYSA-N 0.000 description 1
125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 1
102100027499 5-hydroxytryptamine receptor 1B Human genes 0.000 description 1
101710138639 5-hydroxytryptamine receptor 1B Proteins 0.000 description 1
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
244000215068 Acacia senegal Species 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
229920001817 Agar Polymers 0.000 description 1
208000008811 Agoraphobia Diseases 0.000 description 1
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
208000024827 Alzheimer disease Diseases 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical class [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
241000416162 Astragalus gummifer Species 0.000 description 1
KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
208000020401 Depressive disease Diseases 0.000 description 1
229920002307 Dextran Polymers 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
102000015554 Dopamine receptor Human genes 0.000 description 1
108050004812 Dopamine receptor Proteins 0.000 description 1
LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 description 1
239000004593 Epoxy Substances 0.000 description 1
229920000084 Gum arabic Polymers 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
108010093096 Immobilized Enzymes Proteins 0.000 description 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 description 1
229930195725 Mannitol Natural products 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
240000007594 Oryza sativa Species 0.000 description 1
235000007164 Oryza sativa Nutrition 0.000 description 1
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
LCTONWCANYUPML-UHFFFAOYSA-M Pyruvate Chemical compound CC(=O)C([O-])=O LCTONWCANYUPML-UHFFFAOYSA-M 0.000 description 1
KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
235000021355 Stearic acid Nutrition 0.000 description 1
229930006000 Sucrose Natural products 0.000 description 1
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
229920001615 Tragacanth Polymers 0.000 description 1
235000021307 Triticum Nutrition 0.000 description 1
244000098338 Triticum aestivum Species 0.000 description 1
208000034699 Vitreous floaters Diseases 0.000 description 1
240000008042 Zea mays Species 0.000 description 1
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
235000002017 Zea mays subsp mays Nutrition 0.000 description 1
XEGPJINKFTXZGH-GFCCVEGCSA-N [(4R)-2-oxo-3-(propan-2-ylamino)-1,3-oxazolidin-4-yl]methyl 4-methylbenzenesulfonate Chemical compound C(C)(C)NN1C(OC[C@@H]1COS(=O)(=O)C1=CC=C(C)C=C1)=O XEGPJINKFTXZGH-GFCCVEGCSA-N 0.000 description 1
SRKDUHUULIWXFT-LLVKDONJSA-N [(4r)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OC[C@@H]1OC(C)(C)OC1 SRKDUHUULIWXFT-LLVKDONJSA-N 0.000 description 1
235000010489 acacia gum Nutrition 0.000 description 1
239000000205 acacia gum Substances 0.000 description 1
DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
238000007171 acid catalysis Methods 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
239000003463 adsorbent Substances 0.000 description 1
239000008272 agar Substances 0.000 description 1
230000016571 aggressive behavior Effects 0.000 description 1
235000010443 alginic acid Nutrition 0.000 description 1
239000000783 alginic acid Substances 0.000 description 1
229920000615 alginic acid Polymers 0.000 description 1
229960001126 alginic acid Drugs 0.000 description 1
150000004781 alginic acids Chemical class 0.000 description 1
150000001335 aliphatic alkanes Chemical class 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
150000008041 alkali metal carbonates Chemical class 0.000 description 1
238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
235000011114 ammonium hydroxide Nutrition 0.000 description 1
230000008485 antagonism Effects 0.000 description 1
239000005557 antagonist Substances 0.000 description 1
230000000049 anti-anxiety effect Effects 0.000 description 1
230000036506 anxiety Effects 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
125000005002 aryl methyl group Chemical group 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
230000006399 behavior Effects 0.000 description 1
SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
150000008107 benzenesulfonic acids Chemical class 0.000 description 1
NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 description 1
238000009835 boiling Methods 0.000 description 1
FUFJGUQYACFECW-UHFFFAOYSA-L calcium hydrogenphosphate Chemical compound [Ca+2].OP([O-])([O-])=O FUFJGUQYACFECW-UHFFFAOYSA-L 0.000 description 1
235000011010 calcium phosphates Nutrition 0.000 description 1
CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
235000013539 calcium stearate Nutrition 0.000 description 1
239000008116 calcium stearate Substances 0.000 description 1
239000001768 carboxy methyl cellulose Substances 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 1
239000012876 carrier material Substances 0.000 description 1
230000008859 change Effects 0.000 description 1
238000012512 characterization method Methods 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
XENVCRGQTABGKY-ZHACJKMWSA-N chlorohydrin Chemical compound CC#CC#CC#CC#C\C=C\C(Cl)CO XENVCRGQTABGKY-ZHACJKMWSA-N 0.000 description 1
150000003945 chlorohydrins Chemical class 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
239000012230 colorless oil Substances 0.000 description 1
238000004891 communication Methods 0.000 description 1
231100000867 compulsive behavior Toxicity 0.000 description 1
230000001143 conditioned effect Effects 0.000 description 1
238000010276 construction Methods 0.000 description 1
235000005822 corn Nutrition 0.000 description 1
150000003983 crown ethers Chemical class 0.000 description 1
239000012043 crude product Substances 0.000 description 1
239000013078 crystal Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
WZHCOOQXZCIUNC-UHFFFAOYSA-N cyclandelate Chemical compound C1C(C)(C)CC(C)CC1OC(=O)C(O)C1=CC=CC=C1 WZHCOOQXZCIUNC-UHFFFAOYSA-N 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
235000019700 dicalcium phosphate Nutrition 0.000 description 1
150000001991 dicarboxylic acids Chemical class 0.000 description 1
235000014113 dietary fatty acids Nutrition 0.000 description 1
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
230000004069 differentiation Effects 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
231100000673 dose–response relationship Toxicity 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003814 drug Substances 0.000 description 1
239000000975 dye Substances 0.000 description 1
238000010828 elution Methods 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 description 1
229940093471 ethyl oleate Drugs 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000002360 explosive Substances 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
229930195729 fatty acid Natural products 0.000 description 1
238000003818 flash chromatography Methods 0.000 description 1
CTIKAHQFRQTTAY-UHFFFAOYSA-N fluoro(trimethyl)silane Chemical compound C[Si](C)(C)F CTIKAHQFRQTTAY-UHFFFAOYSA-N 0.000 description 1
238000004108 freeze drying Methods 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
239000007903 gelatin capsule Substances 0.000 description 1
230000003370 grooming effect Effects 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
239000008240 homogeneous mixture Substances 0.000 description 1
150000004677 hydrates Chemical class 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
229910001872 inorganic gas Inorganic materials 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
238000005342 ion exchange Methods 0.000 description 1
238000002955 isolation Methods 0.000 description 1
LYBKPDDZTNUNNM-UHFFFAOYSA-N isopropylbenzylamine Chemical compound CC(C)NCC1=CC=CC=C1 LYBKPDDZTNUNNM-UHFFFAOYSA-N 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
230000003137 locomotive effect Effects 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
239000001630 malic acid Substances 0.000 description 1
235000011090 malic acid Nutrition 0.000 description 1
239000000594 mannitol Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
244000005700 microbiome Species 0.000 description 1
239000011707 mineral Substances 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
238000002156 mixing Methods 0.000 description 1
AJUXDFHPVZQOGF-UHFFFAOYSA-N n,n-dimethyl-1-naphthylamine Chemical compound C1=CC=C2C(N(C)C)=CC=CC2=C1 AJUXDFHPVZQOGF-UHFFFAOYSA-N 0.000 description 1
UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
235000015097 nutrients Nutrition 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
239000003791 organic solvent mixture Substances 0.000 description 1
150000002905 orthoesters Chemical class 0.000 description 1
MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
239000000049 pigment Substances 0.000 description 1
239000004014 plasticizer Substances 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
229910003446 platinum oxide Inorganic materials 0.000 description 1
230000001242 postsynaptic effect Effects 0.000 description 1
229920001592 potato starch Polymers 0.000 description 1
229940116317 potato starch Drugs 0.000 description 1
230000003518 presynaptic effect Effects 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
125000000168 pyrrolyl group Chemical group 0.000 description 1
239000003087 receptor blocking agent Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
229960003147 reserpine Drugs 0.000 description 1
230000004044 response Effects 0.000 description 1
229910052703 rhodium Inorganic materials 0.000 description 1
239000010948 rhodium Substances 0.000 description 1
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
235000009566 rice Nutrition 0.000 description 1
229940100486 rice starch Drugs 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
238000007142 ring opening reaction Methods 0.000 description 1
229910052707 ruthenium Inorganic materials 0.000 description 1
238000012216 screening Methods 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000008159 sesame oil Substances 0.000 description 1
235000011803 sesame oil Nutrition 0.000 description 1
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
235000010413 sodium alginate Nutrition 0.000 description 1
239000000661 sodium alginate Substances 0.000 description 1
229940005550 sodium alginate Drugs 0.000 description 1
235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
235000002639 sodium chloride Nutrition 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
239000007901 soft capsule Substances 0.000 description 1
229950001675 spiperone Drugs 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
IIACRCGMVDHOTQ-UHFFFAOYSA-M sulfamate Chemical compound NS([O-])(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-M 0.000 description 1
IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid group Chemical class S(N)(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
229910021653 sulphate ion Inorganic materials 0.000 description 1
239000002511 suppository base Substances 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
239000004408 titanium dioxide Substances 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
229940116362 tragacanth Drugs 0.000 description 1
229940078499 tricalcium phosphate Drugs 0.000 description 1
235000019731 tricalcium phosphate Nutrition 0.000 description 1
229910000391 tricalcium phosphate Inorganic materials 0.000 description 1
125000005951 trifluoromethanesulfonyloxy group Chemical group 0.000 description 1
239000005051 trimethylchlorosilane Substances 0.000 description 1
125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
229940100445 wheat starch Drugs 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two 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
- C07D207/33—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two 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 with substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/333—Radicals substituted by oxygen or sulfur atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two 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
- C07D207/325—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two 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 with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Epidemiology (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

NO874425A 1986-10-24 1987-10-23 Fremgangsmaate til fremstilling av (+)-1-isopropylamino-3-(o-pyrrol-l-yl)-fenoksy)-2-propanol og dets salter. NO874425L (no)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
CH4235/86A CH668185A5 (de)	1986-10-24	1986-10-24	Verwendung von 1-isopropylamino-3-(o-(1-pyrrolyl)-phenoxy)-2-propanol zur herstellung von pharmazeutischen praeparaten.
CH17887		1987-01-19
CH92687		1987-03-12
CH92587		1987-03-12

Publications (2)

Publication Number	Publication Date
NO874425D0 NO874425D0 (no)	1987-10-23
NO874425L true NO874425L (no)	1988-04-25

Family

ID=27427782

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO874425A NO874425L (no)	1986-10-24	1987-10-23	Fremgangsmaate til fremstilling av (+)-1-isopropylamino-3-(o-pyrrol-l-yl)-fenoksy)-2-propanol og dets salter.

Country Status (16)

Country	Link
EP (1)	EP0265388A1 (xx)
KR (1)	KR880005094A (xx)
AT (1)	ATA281087A (xx)
BE (1)	BE1002060A3 (xx)
DE (1)	DE3735641A1 (xx)
DK (1)	DK554887A (xx)
FI (1)	FI874643A (xx)
FR (1)	FR2605629A1 (xx)
GB (1)	GB2197315A (xx)
GR (1)	GR871634B (xx)
HU (1)	HUT45492A (xx)
IE (1)	IE872860L (xx)
NL (1)	NL8702533A (xx)
NO (1)	NO874425L (xx)
PT (1)	PT85976B (xx)
SE (1)	SE8704093L (xx)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0265388A1 (de) *	1986-10-24	1988-04-27	Ciba-Geigy Ag	Pyrrol-Derivate, therapeutische Mittel, die sie enthalten und ihre Verwendung
JPH02131465A (ja) *	1988-07-18	1990-05-21	Nippon Tokushu Noyaku Seizo Kk	１−フエニルピロール類及び除草剤としての利用

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AR204241A1 (es) *	1973-03-09	1975-12-10	Ciba Geigy Ag	Procedimiento para preparar compuestos derivados del 1-pirrolil(1)-fenoxi-2-hidroxi-3-alquilamino-propano y del 1-pirrolil-(1)-fenoxi-3-hidroxi-3-morfolino-propano
DE2835438A1 (de) *	1978-08-12	1980-03-06	Basf Ag	Aminopropanolderivate des 2-(o-hydroxyphenyl)-pyrrols
EP0152379A3 (de) *	1984-02-15	1986-10-29	Ciba-Geigy Ag	Verfahren zur Herstellung von pharmazeutischen Zusammensetzungen enthaltend unilamellare Liposomen
EP0265388A1 (de) *	1986-10-24	1988-04-27	Ciba-Geigy Ag	Pyrrol-Derivate, therapeutische Mittel, die sie enthalten und ihre Verwendung

1987
- 1987-10-19 EP EP87810604A patent/EP0265388A1/de not_active Withdrawn
- 1987-10-21 FI FI874643A patent/FI874643A/fi not_active Application Discontinuation
- 1987-10-21 SE SE8704093A patent/SE8704093L/xx not_active Application Discontinuation
- 1987-10-21 GB GB08724670A patent/GB2197315A/en not_active Withdrawn
- 1987-10-21 DE DE19873735641 patent/DE3735641A1/de not_active Withdrawn
- 1987-10-22 FR FR8714607A patent/FR2605629A1/fr not_active Withdrawn
- 1987-10-22 GR GR871634A patent/GR871634B/el unknown
- 1987-10-22 PT PT85976A patent/PT85976B/pt unknown
- 1987-10-23 AT AT0281087A patent/ATA281087A/de not_active Application Discontinuation
- 1987-10-23 BE BE8701205A patent/BE1002060A3/fr not_active IP Right Cessation
- 1987-10-23 KR KR870011762A patent/KR880005094A/ko not_active Application Discontinuation
- 1987-10-23 NL NL8702533A patent/NL8702533A/nl not_active Application Discontinuation
- 1987-10-23 NO NO874425A patent/NO874425L/no unknown
- 1987-10-23 DK DK554887A patent/DK554887A/da not_active Application Discontinuation
- 1987-10-23 HU HU874756A patent/HUT45492A/hu unknown
- 1987-10-23 IE IE872860A patent/IE872860L/xx unknown

Also Published As

Publication number	Publication date
PT85976B (de)	1990-01-19
FR2605629A1 (fr)	1988-04-29
GR871634B (en)	1988-02-24
FI874643A0 (fi)	1987-10-21
SE8704093D0 (sv)	1987-10-21
IE872860L (en)	1988-04-24
DK554887D0 (da)	1987-10-23
ATA281087A (de)	1989-01-15
KR880005094A (ko)	1988-06-28
BE1002060A3 (fr)	1990-06-12
PT85976A (de)	1987-11-01
HUT45492A (en)	1988-07-28
GB2197315A (en)	1988-05-18
DK554887A (da)	1988-04-05
NL8702533A (nl)	1988-05-16
DE3735641A1 (de)	1988-04-28
FI874643A (fi)	1988-04-25
EP0265388A1 (de)	1988-04-27
SE8704093L (sv)	1988-04-25
NO874425D0 (no)	1987-10-23

Publication	Publication Date	Title
DK170637B1 (da)	1995-11-20	1-phenyl-3-naphthalenyloxypropanaminer, fremgangsmåde til fremstilling af sådanne forbindelser og farmaceutiske præparater indeholdende disse
EP2403823B1 (en)	2015-10-21	Process for the preparation of cinacalcet and salts thereof, and intermediates for use in the process
NO159267B (no)	1988-09-05	Fremgangsmaate for spalting av en racemisk modifikasjon avbeta-adrenerge aryl- eller hetaryloksypropanolaminer.
JP4422331B2 (ja)	2010-02-24	アゼチジン誘導体およびピロリジン誘導体
WO1998031677A1 (fr)	1998-07-23	Nouvelles amines aromatiques derivees d'amines cycliques utiles comme medicaments
JP3606326B2 (ja)	2005-01-05	欝病、不安神経症およびパーキンソン病を治療するための１−アリールシクロアルキルスルフィド、スルホキシドおよびスルホン
WO1998031669A1 (fr)	1998-07-23	Nouvelles arylpiperazines derivees de piperidine comme medicaments antidepresseurs
US8552219B2 (en)	2013-10-08	Process for preparing L-phenyl-3-dimethylaminopropane derivative
JPS6326099B2 (xx)	1988-05-27
NO874425L (no)	1988-04-25	Fremgangsmaate til fremstilling av (+)-1-isopropylamino-3-(o-pyrrol-l-yl)-fenoksy)-2-propanol og dets salter.
US5149714A (en)	1992-09-22	Antidepressants
EP0074873B1 (fr)	1984-11-21	Dérivés de phénoxy-3 propanol-2, leur préparation et leur application en thérapeutique
US5173502A (en)	1992-12-22	Substituted trifluoropropan-1-yl-imidazole alpha 2-receptor anagonists
EP0322263B1 (fr)	1994-03-30	Carbamates tricycliques, leur procédé de préparation et leur application en thérapeutique
RU2203896C2 (ru)	2003-05-10	Производное пиперидинилметилоксазолидинона, способ его получения, фармацевтическая композиция и способ ее получения
EP1187824B1 (fr)	2002-11-13	Derives de [(2-substitue-5-[3-thienyl)-benzyl]-[2-([2-isopropoxy-5-fluoro]-phenoxy)-ethyl]-amine, leur procede de preparation et leur utilisation a titre de medicaments
EP0209275B1 (en)	1988-10-19	Benz-trisubstituted 2-aminotetralins
EP0520882B1 (fr)	1995-07-12	Dérivés de 2-aminopyrimidine-4-carboxamide, leur préparation et leur application en thérapeutique
EP0259228B1 (fr)	1992-06-03	Dérivés 5-aminoéthylés de l'oxazolidinone-2, leur procédé de préparation et leur application en thérapeutique
FR2741071A1 (fr)	1997-05-16	Derives de 3-(benzofuran-5-yl)oxazolidin-2-one, leur preparation et leur application en therapeutique
EP0820434B1 (fr)	2000-08-09	Derives de la phenoxyethylamine possedant une haute affinite pour le recepteur 5-ht 1a, leur procede de preparation, leur application comme medicament et les compositions pharmaceutiques les renfermant
EP0929525B1 (fr)	2002-09-04	Heteroaryloxyethylamines comme ligands du recepteur 5-ht1a
EP0569276B1 (fr)	1997-01-29	Nouvelle application des enantiomères dérivés du (S)-amino-2-dichloro-3,4-benzyl)-2-propanol-1
FR2775687A1 (fr)	1999-09-10	Nouveaux composes du benzocyclobutane, leur procede de preparation et les compositions pharmaceutiques qui les contiennent
JPS63115858A (ja)	1988-05-20	医薬組成物