IE45320B1

IE45320B1 - 2-benzylpyrolidines,process for their preparation and pharmaceutical compositions containing them

2-benzylpyrolidines,process for their preparation and pharmaceutical compositions containing them

Info

Publication number: IE45320B1
Authority: IE; Ireland
Prior art keywords: group; methylpyrrolidine; addition salts; carbon atoms; acid addition
Prior art date: 1976-07-28

Application number

IE1567/77A

Other languages

English (en)

Other versions

IE45320L (en

Original Assignee

Byk Gulden Lomberg Chem Fab

Priority date

1976-07-28

Filing date

1977-07-27

Publication date

1982-07-28

1977-07-27 Application filed by Byk Gulden Lomberg Chem Fab filed Critical Byk Gulden Lomberg Chem Fab

1978-01-28 Publication of IE45320L publication Critical patent/IE45320L/xx

1982-07-28 Publication of IE45320B1 publication Critical patent/IE45320B1/en

Links

238000000034 method Methods 0.000 title claims description 58
230000008569 process Effects 0.000 title claims description 24
238000002360 preparation method Methods 0.000 title claims description 16
239000008194 pharmaceutical composition Substances 0.000 title claims 3
NKHMSOXIXROFRU-UHFFFAOYSA-N 2-benzylpyrrolidine Chemical group C=1C=CC=CC=1CC1CCCN1 NKHMSOXIXROFRU-UHFFFAOYSA-N 0.000 claims abstract description 32
125000001424 substituent group Chemical group 0.000 claims abstract description 18
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 11
230000036772 blood pressure Effects 0.000 claims abstract description 10
-1 alicyclic hydrocarbon radical Chemical class 0.000 claims description 110
150000001875 compounds Chemical class 0.000 claims description 68
150000003839 salts Chemical class 0.000 claims description 62
239000002253 acid Substances 0.000 claims description 60
125000004432 carbon atom Chemical group C* 0.000 claims description 56
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 40
239000002585 base Substances 0.000 claims description 26
125000003277 amino group Chemical group 0.000 claims description 22
125000000217 alkyl group Chemical group 0.000 claims description 21
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 21
125000005843 halogen group Chemical group 0.000 claims description 20
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 20
125000003545 alkoxy group Chemical group 0.000 claims description 19
229930195733 hydrocarbon Natural products 0.000 claims description 18
125000003710 aryl alkyl group Chemical group 0.000 claims description 15
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
239000004215 Carbon black (E152) Substances 0.000 claims description 13
125000004423 acyloxy group Chemical group 0.000 claims description 13
IQGVUZCAENHORR-UHFFFAOYSA-N 2-[(4-chlorophenyl)methyl]pyrrolidine Chemical compound C1=CC(Cl)=CC=C1CC1NCCC1 IQGVUZCAENHORR-UHFFFAOYSA-N 0.000 claims description 11
125000001931 aliphatic group Chemical group 0.000 claims description 11
239000007788 liquid Substances 0.000 claims description 11
125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 9
239000012458 free base Substances 0.000 claims description 9
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
230000036407 pain Effects 0.000 claims description 9
238000011282 treatment Methods 0.000 claims description 9
239000000460 chlorine Substances 0.000 claims description 7
229910052801 chlorine Inorganic materials 0.000 claims description 7
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 7
JNKCIXCNBFFNHD-UHFFFAOYSA-N 2-[(4-chlorophenyl)methyl]-1-methylpyrrolidine Chemical compound CN1CCCC1CC1=CC=C(Cl)C=C1 JNKCIXCNBFFNHD-UHFFFAOYSA-N 0.000 claims description 6
VDSNKERDALCECS-UHFFFAOYSA-N 4-[(1-methylpyrrolidin-2-yl)methyl]aniline Chemical compound CN1CCCC1CC1=CC=C(N)C=C1 VDSNKERDALCECS-UHFFFAOYSA-N 0.000 claims description 6
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
125000006196 aroyl alkyl group Chemical group 0.000 claims description 6
239000007787 solid Substances 0.000 claims description 6
AVFZOVWCLRSYKC-UHFFFAOYSA-N 1-methylpyrrolidine Chemical class CN1CCCC1 AVFZOVWCLRSYKC-UHFFFAOYSA-N 0.000 claims description 5
YGWNSMNBSSEOTC-UHFFFAOYSA-N 2-[(2-chlorophenyl)methyl]-1-methylpyrrolidine Chemical compound CN1CCCC1CC1=CC=CC=C1Cl YGWNSMNBSSEOTC-UHFFFAOYSA-N 0.000 claims description 5
210000003169 central nervous system Anatomy 0.000 claims description 5
125000004663 dialkyl amino group Chemical group 0.000 claims description 5
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
150000003254 radicals Chemical class 0.000 claims description 5
AYCAOTJKOPNLPV-UHFFFAOYSA-N 2-[(3-chlorophenyl)methyl]-1-methylpyrrolidine Chemical compound CN1CCCC1CC1=CC=CC(Cl)=C1 AYCAOTJKOPNLPV-UHFFFAOYSA-N 0.000 claims description 4
YKTRGSOHLRFGAD-UHFFFAOYSA-N 2-[(3-methoxyphenyl)methyl]-1-methylpyrrolidine Chemical compound COC1=CC=CC(CC2N(CCC2)C)=C1 YKTRGSOHLRFGAD-UHFFFAOYSA-N 0.000 claims description 4
YUOONPHJWMUTKO-UHFFFAOYSA-N 3-[(1-methylpyrrolidin-2-yl)methyl]phenol Chemical compound CN1CCCC1CC1=CC=CC(O)=C1 YUOONPHJWMUTKO-UHFFFAOYSA-N 0.000 claims description 4
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 4
229910052731 fluorine Inorganic materials 0.000 claims description 4
239000011737 fluorine Substances 0.000 claims description 4
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 3
125000000753 cycloalkyl group Chemical group 0.000 claims description 3
229910052736 halogen Inorganic materials 0.000 claims description 3
JIOKETBRNHZBHM-UHFFFAOYSA-N 2-[(2-methoxyphenyl)methyl]-1-methylpyrrolidine Chemical compound COC1=CC=CC=C1CC1N(C)CCC1 JIOKETBRNHZBHM-UHFFFAOYSA-N 0.000 claims description 2
SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 claims description 2
125000000524 functional group Chemical group 0.000 claims description 2
150000002367 halogens Chemical class 0.000 claims description 2
231100000915 pathological change Toxicity 0.000 claims description 2
230000036285 pathological change Effects 0.000 claims description 2
125000003884 phenylalkyl group Chemical class 0.000 claims description 2
239000002243 precursor Substances 0.000 claims description 2
239000000969 carrier Substances 0.000 claims 2
239000004480 active ingredient Substances 0.000 claims 1
239000002689 soil Substances 0.000 claims 1
239000000203 mixture Substances 0.000 abstract description 50
239000003814 drug Substances 0.000 abstract description 22
241001465754 Metazoa Species 0.000 abstract description 11
230000008058 pain sensation Effects 0.000 abstract description 2
238000007796 conventional method Methods 0.000 abstract 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 236
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 225
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 113
239000000243 solution Substances 0.000 description 111
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 84
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 82
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 81
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 56
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 55
239000002904 solvent Substances 0.000 description 54
238000006243 chemical reaction Methods 0.000 description 50
239000003921 oil Substances 0.000 description 44
235000019198 oils Nutrition 0.000 description 44
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 41
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 39
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
238000010992 reflux Methods 0.000 description 35
238000003756 stirring Methods 0.000 description 35
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 35
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 30
239000003054 catalyst Substances 0.000 description 29
AHVYPIQETPWLSZ-UHFFFAOYSA-N N-methyl-pyrrolidine Natural products CN1CC=CC1 AHVYPIQETPWLSZ-UHFFFAOYSA-N 0.000 description 28
238000001035 drying Methods 0.000 description 28
229910052938 sodium sulfate Inorganic materials 0.000 description 28
235000011152 sodium sulphate Nutrition 0.000 description 28
239000001257 hydrogen Substances 0.000 description 27
229910052739 hydrogen Inorganic materials 0.000 description 27
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 25
239000013543 active substance Substances 0.000 description 23
238000001816 cooling Methods 0.000 description 22
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 21
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
238000009835 boiling Methods 0.000 description 21
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 20
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 19
238000000605 extraction Methods 0.000 description 19
239000000155 melt Substances 0.000 description 19
239000011734 sodium Substances 0.000 description 19
229910052708 sodium Inorganic materials 0.000 description 19
235000015424 sodium Nutrition 0.000 description 19
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
239000012071 phase Substances 0.000 description 18
230000000694 effects Effects 0.000 description 17
229910052697 platinum Inorganic materials 0.000 description 17
239000007858 starting material Substances 0.000 description 17
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 16
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
229940075930 picrate Drugs 0.000 description 16
OXNIZHLAWKMVMX-UHFFFAOYSA-M picrate anion Chemical compound [O-]C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-M 0.000 description 16
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 15
229960000583 acetic acid Drugs 0.000 description 15
238000001914 filtration Methods 0.000 description 15
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 14
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 14
239000013078 crystal Substances 0.000 description 13
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 13
230000009467 reduction Effects 0.000 description 13
238000006722 reduction reaction Methods 0.000 description 13
239000000706 filtrate Substances 0.000 description 12
239000012442 inert solvent Substances 0.000 description 11
229910052757 nitrogen Inorganic materials 0.000 description 11
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 10
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 10
238000004821 distillation Methods 0.000 description 10
239000005457 ice water Substances 0.000 description 10
239000012074 organic phase Substances 0.000 description 10
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
239000000047 product Substances 0.000 description 10
150000003235 pyrrolidines Chemical class 0.000 description 10
239000011541 reaction mixture Substances 0.000 description 10
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 9
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 9
239000000126 substance Substances 0.000 description 9
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 8
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 8
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 8
241000282414 Homo sapiens Species 0.000 description 8
241000699670 Mus sp. Species 0.000 description 8
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 8
230000000202 analgesic effect Effects 0.000 description 8
LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 8
230000007062 hydrolysis Effects 0.000 description 8
238000006460 hydrolysis reaction Methods 0.000 description 8
239000012280 lithium aluminium hydride Substances 0.000 description 8
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 8
239000000546 pharmaceutical excipient Substances 0.000 description 8
UEWDJCZJEIBPKX-UHFFFAOYSA-N 2,2-diethoxy-1-methylpyrrolidine Chemical compound CCOC1(OCC)CCCN1C UEWDJCZJEIBPKX-UHFFFAOYSA-N 0.000 description 7
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 7
239000007868 Raney catalyst Substances 0.000 description 7
229910000564 Raney nickel Inorganic materials 0.000 description 7
238000006114 decarboxylation reaction Methods 0.000 description 7
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 7
239000002244 precipitate Substances 0.000 description 7
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
239000000741 silica gel Substances 0.000 description 7
229910002027 silica gel Inorganic materials 0.000 description 7
238000012360 testing method Methods 0.000 description 7
230000001225 therapeutic effect Effects 0.000 description 7
GNWIZUYPDFJIRT-UHFFFAOYSA-N 2-benzyl-1-methylpyrrolidine Chemical compound CN1CCCC1CC1=CC=CC=C1 GNWIZUYPDFJIRT-UHFFFAOYSA-N 0.000 description 6
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 6
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-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 6
241000699666 Mus <mouse, genus> Species 0.000 description 6
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 6
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
150000001298 alcohols Chemical class 0.000 description 6
229910052783 alkali metal Inorganic materials 0.000 description 6
150000001340 alkali metals Chemical class 0.000 description 6
230000015572 biosynthetic process Effects 0.000 description 6
239000003795 chemical substances by application Substances 0.000 description 6
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 6
150000002148 esters Chemical class 0.000 description 6
239000012259 ether extract Substances 0.000 description 6
150000002170 ethers Chemical class 0.000 description 6
239000008187 granular material Substances 0.000 description 6
239000008101 lactose Substances 0.000 description 6
229910017604 nitric acid Inorganic materials 0.000 description 6
239000003208 petroleum Substances 0.000 description 6
230000000144 pharmacologic effect Effects 0.000 description 6
229910000029 sodium carbonate Inorganic materials 0.000 description 6
239000001117 sulphuric acid Substances 0.000 description 6
235000011149 sulphuric acid Nutrition 0.000 description 6
239000000454 talc Substances 0.000 description 6
235000012222 talc Nutrition 0.000 description 6
229910052623 talc Inorganic materials 0.000 description 6
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 6
206010015995 Eyelid ptosis Diseases 0.000 description 5
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 5
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 5
150000001412 amines Chemical class 0.000 description 5
230000006399 behavior Effects 0.000 description 5
239000001569 carbon dioxide Substances 0.000 description 5
229910002092 carbon dioxide Inorganic materials 0.000 description 5
235000003599 food sweetener Nutrition 0.000 description 5
150000002430 hydrocarbons Chemical class 0.000 description 5
229910052740 iodine Inorganic materials 0.000 description 5
229910052763 palladium Inorganic materials 0.000 description 5
239000000825 pharmaceutical preparation Substances 0.000 description 5
229910000027 potassium carbonate Inorganic materials 0.000 description 5
239000000843 powder Substances 0.000 description 5
201000003004 ptosis Diseases 0.000 description 5
238000000746 purification Methods 0.000 description 5
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 5
239000003765 sweetening agent Substances 0.000 description 5
239000008096 xylene Substances 0.000 description 5
DNXIKVLOVZVMQF-UHFFFAOYSA-N (3beta,16beta,17alpha,18beta,20alpha)-17-hydroxy-11-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-yohimban-16-carboxylic acid, methyl ester Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(C(=O)OC)C(O)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 DNXIKVLOVZVMQF-UHFFFAOYSA-N 0.000 description 4
UCTWMZQNUQWSLP-VIFPVBQESA-N (R)-adrenaline Chemical compound CNC[C@H](O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-VIFPVBQESA-N 0.000 description 4
VSXPCTDBJXVULY-UHFFFAOYSA-N 2-[(4-bromophenyl)methyl]-1-methylpyrrolidine Chemical compound CN1CCCC1CC1=CC=C(Br)C=C1 VSXPCTDBJXVULY-UHFFFAOYSA-N 0.000 description 4
IVYMIRMKXZAHRV-UHFFFAOYSA-N 4-chlorophenylacetonitrile Chemical compound ClC1=CC=C(CC#N)C=C1 IVYMIRMKXZAHRV-UHFFFAOYSA-N 0.000 description 4
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
208000009132 Catalepsy Diseases 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
229920002261 Corn starch Polymers 0.000 description 4
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
235000019759 Maize starch Nutrition 0.000 description 4
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
238000007126 N-alkylation reaction Methods 0.000 description 4
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