CH507947A - Verfahren zur Herstellung neuer azabicycloaliphatischer Verbindungen - Google Patents

Verfahren zur Herstellung neuer azabicycloaliphatischer Verbindungen

Info

Publication number: CH507947A
Authority: CH; Switzerland
Prior art keywords: group; aza; carbon atoms; alk; het
Prior art date: 1966-07-27

Application number

CH1673468A

Other languages

German (de)

English (en)

Inventor

Prakash Dr Arya Vishwa

Original Assignee

Ciba Geigy Ag

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.)

1966-07-27

Filing date

1966-07-27

Publication date

1971-05-31

1966-07-27 Application filed by Ciba Geigy Ag filed Critical Ciba Geigy Ag

1966-07-27 Priority to CH1673568A priority Critical patent/CH486463A/de

1966-07-27 Priority to CH1088966A priority patent/CH508626A/de

1966-07-27 Priority to CH1673468A priority patent/CH507947A/de

1967-07-19 Priority to DE1967C0042904 priority patent/DE1670448B2/de

1967-07-20 Priority to FR1549235D priority patent/FR1549235A/fr

1967-07-24 Priority to GB33851/67A priority patent/GB1195729A/en

1967-07-26 Priority to BE701861D priority patent/BE701861A/xx

1967-10-12 Priority to FR124193A priority patent/FR7320M/fr

1967-10-12 Priority to FR124194A priority patent/FR7074M/fr

1971-05-31 Publication of CH507947A publication Critical patent/CH507947A/de

Links

230000002908 adrenolytic effect Effects 0.000 title abstract description 3
239000000674 adrenergic antagonist Substances 0.000 title 1
239000005555 hypertensive agent Substances 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 61
150000003839 salts Chemical class 0.000 claims abstract description 58
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 47
239000002253 acid Substances 0.000 claims abstract description 44
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 15
125000003118 aryl group Chemical group 0.000 claims abstract description 13
125000002950 monocyclic group Chemical group 0.000 claims abstract description 10
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 9
125000002947 alkylene group Chemical group 0.000 claims abstract description 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 136
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 128
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 92
-1 3- [4- (3,4-Dimethyl-phenyl) -4-oxo-1-n-butyl] -3-aza-bicyclo [3,2,2] nonane Chemical compound 0.000 claims description 89
239000000203 mixture Substances 0.000 claims description 54
238000000034 method Methods 0.000 claims description 45
239000000155 melt Substances 0.000 claims description 43
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 41
238000001953 recrystallisation Methods 0.000 claims description 34
ZCYXXKJEDCHMGH-UHFFFAOYSA-N nonane Chemical compound CCCC[CH]CCCC ZCYXXKJEDCHMGH-UHFFFAOYSA-N 0.000 claims description 22
BKIMMITUMNQMOS-UHFFFAOYSA-N normal nonane Natural products CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 claims description 22
125000000217 alkyl group Chemical group 0.000 claims description 21
239000011541 reaction mixture Substances 0.000 claims description 18
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 15
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 14
229910052757 nitrogen Inorganic materials 0.000 claims description 14
125000002524 organometallic group Chemical group 0.000 claims description 13
229910052799 carbon Inorganic materials 0.000 claims description 12
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 11
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 11
125000003545 alkoxy group Chemical group 0.000 claims description 10
230000001419 dependent effect Effects 0.000 claims description 10
125000005843 halogen group Chemical group 0.000 claims description 10
150000003254 radicals Chemical class 0.000 claims description 10
125000004433 nitrogen atom Chemical group N* 0.000 claims description 9
239000007858 starting material Substances 0.000 claims description 9
238000006243 chemical reaction Methods 0.000 claims description 8
239000001257 hydrogen Substances 0.000 claims description 8
229910052739 hydrogen Inorganic materials 0.000 claims description 8
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
239000003153 chemical reaction reagent Substances 0.000 claims description 7
150000004820 halides Chemical class 0.000 claims description 7
238000002360 preparation method Methods 0.000 claims description 7
125000001931 aliphatic group Chemical group 0.000 claims description 6
150000002681 magnesium compounds Chemical class 0.000 claims description 6
150000002825 nitriles Chemical class 0.000 claims description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
150000001408 amides Chemical class 0.000 claims description 5
239000003054 catalyst Substances 0.000 claims description 5
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
125000002837 carbocyclic group Chemical group 0.000 claims description 4
YZCKVEUIGOORGS-UHFFFAOYSA-N Hydrogen atom Chemical compound [H] YZCKVEUIGOORGS-UHFFFAOYSA-N 0.000 claims description 3
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 3
229940065285 cadmium compound Drugs 0.000 claims description 3
150000001662 cadmium compounds Chemical class 0.000 claims description 3
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
238000000354 decomposition reaction Methods 0.000 claims description 3
150000002641 lithium Chemical class 0.000 claims description 3
229910003002 lithium salt Inorganic materials 0.000 claims description 3
159000000002 lithium salts Chemical class 0.000 claims description 3
150000002736 metal compounds Chemical class 0.000 claims description 3
229910052987 metal hydride Inorganic materials 0.000 claims description 3
150000004681 metal hydrides Chemical class 0.000 claims description 3
125000004076 pyridyl group Chemical group 0.000 claims description 3
150000003752 zinc compounds Chemical class 0.000 claims description 3
125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
125000004861 4-isopropyl phenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
125000003435 aroyl group Chemical group 0.000 claims description 2
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
229910052740 iodine Inorganic materials 0.000 claims description 2
HWYHDWGGACRVEH-UHFFFAOYSA-N n-methyl-n-(4-pyrrolidin-1-ylbut-2-ynyl)acetamide Chemical compound CC(=O)N(C)CC#CCN1CCCC1 HWYHDWGGACRVEH-UHFFFAOYSA-N 0.000 claims description 2
229910052702 rhenium Inorganic materials 0.000 claims 2
LVGDWVVFKLHIAQ-UHFFFAOYSA-N 4-(3-azabicyclo[3.2.2]nonan-5-yl)-1-(4-fluorophenyl)butan-1-one Chemical compound C1=CC(F)=CC=C1C(=O)CCCC1(CNC2)CCC2CC1 LVGDWVVFKLHIAQ-UHFFFAOYSA-N 0.000 claims 1
239000000543 intermediate Substances 0.000 abstract description 3
229910052760 oxygen Inorganic materials 0.000 abstract description 3
239000001301 oxygen Substances 0.000 abstract description 3
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical group O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 abstract description 2
230000002936 tranquilizing effect Effects 0.000 abstract description 2
230000002539 anti-aggressive effect Effects 0.000 abstract 1
125000001183 hydrocarbyl group Chemical group 0.000 abstract 1
230000001631 hypertensive effect Effects 0.000 abstract 1
239000000243 solution Substances 0.000 description 64
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 51
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 27
235000011121 sodium hydroxide Nutrition 0.000 description 17
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 12
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
239000007864 aqueous solution Substances 0.000 description 11
239000002585 base Substances 0.000 description 11
239000011777 magnesium Substances 0.000 description 11
229910052749 magnesium Inorganic materials 0.000 description 11
239000002244 precipitate Substances 0.000 description 11
238000003756 stirring Methods 0.000 description 11
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 10
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 10
238000000605 extraction Methods 0.000 description 10
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 9
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 8
238000001816 cooling Methods 0.000 description 8
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 7
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
239000012458 free base Substances 0.000 description 6
239000011976 maleic acid Substances 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
239000002904 solvent Substances 0.000 description 6
MQUXDPJVXLTYED-UHFFFAOYSA-N 4-(3-azabicyclo[3.2.2]nonan-3-yl)-1-(4-fluorophenyl)butan-1-one Chemical compound C1=CC(F)=CC=C1C(=O)CCCN1CC(CC2)CCC2C1 MQUXDPJVXLTYED-UHFFFAOYSA-N 0.000 description 5
LSDPADSPERSYNC-UHFFFAOYSA-N 4-(3-azabicyclo[3.2.2]nonan-3-yl)butanenitrile Chemical compound C(#N)CCCN1CC2CCC(C1)CC2 LSDPADSPERSYNC-UHFFFAOYSA-N 0.000 description 5
235000019270 ammonium chloride Nutrition 0.000 description 5
150000001721 carbon Chemical group 0.000 description 5
239000013078 crystal Substances 0.000 description 5
229910052751 metal Inorganic materials 0.000 description 5
239000002184 metal Substances 0.000 description 5
229920006395 saturated elastomer Polymers 0.000 description 5
LICHZOBEUWVYSY-UHFFFAOYSA-N 3-azabicyclo[3.2.2]nonane Chemical compound C1CC2CCC1CNC2 LICHZOBEUWVYSY-UHFFFAOYSA-N 0.000 description 4
241001465754 Metazoa Species 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
229960000583 acetic acid Drugs 0.000 description 4
150000007513 acids Chemical class 0.000 description 4
230000002180 anti-stress Effects 0.000 description 4
238000009835 boiling Methods 0.000 description 4
239000000460 chlorine Substances 0.000 description 4
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
230000007717 exclusion Effects 0.000 description 4
239000000706 filtrate Substances 0.000 description 4
125000004043 oxo group Chemical group O=* 0.000 description 4
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
AITNMTXHTIIIBB-UHFFFAOYSA-N 1-bromo-4-fluorobenzene Chemical compound FC1=CC=C(Br)C=C1 AITNMTXHTIIIBB-UHFFFAOYSA-N 0.000 description 3
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
125000002252 acyl group Chemical group 0.000 description 3
125000003282 alkyl amino group Chemical group 0.000 description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
229910052801 chlorine Inorganic materials 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
239000012153 distilled water Substances 0.000 description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
239000000284 extract Substances 0.000 description 3
229910052736 halogen Inorganic materials 0.000 description 3
150000002367 halogens Chemical class 0.000 description 3
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
229910000041 hydrogen chloride Inorganic materials 0.000 description 3
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
150000002576 ketones Chemical class 0.000 description 3
BRKADVNLTRCLOW-UHFFFAOYSA-M magnesium;fluorobenzene;bromide Chemical compound [Mg+2].[Br-].FC1=CC=[C-]C=C1 BRKADVNLTRCLOW-UHFFFAOYSA-M 0.000 description 3
DGEYTDCFMQMLTH-UHFFFAOYSA-N methanol;propan-2-ol Chemical compound OC.CC(C)O DGEYTDCFMQMLTH-UHFFFAOYSA-N 0.000 description 3
150000002829 nitrogen Chemical group 0.000 description 3
238000006722 reduction reaction Methods 0.000 description 3
238000010992 reflux Methods 0.000 description 3
229910000029 sodium carbonate Inorganic materials 0.000 description 3
125000001424 substituent group Chemical group 0.000 description 3
239000000725 suspension Substances 0.000 description 3
BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 2
WGRRUUYPWKDEPK-UHFFFAOYSA-N 3-(3-chloropropyl)-3-azabicyclo[3.2.2]nonane Chemical compound C1N(CCCCl)CC2CCC1CC2 WGRRUUYPWKDEPK-UHFFFAOYSA-N 0.000 description 2
XXLFLUJXWKXUGS-UHFFFAOYSA-N 6-methoxyquinoline-4-carboxylic acid Chemical compound N1=CC=C(C(O)=O)C2=CC(OC)=CC=C21 XXLFLUJXWKXUGS-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 2
IGRKSWHNVUZWLF-UHFFFAOYSA-N FC1=CC=C(C=C1)C(CCCN1CC2CCC(C1)CC2)O Chemical compound FC1=CC=C(C=C1)C(CCCN1CC2CCC(C1)CC2)O IGRKSWHNVUZWLF-UHFFFAOYSA-N 0.000 description 2
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 2
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 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
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
125000004423 acyloxy group Chemical group 0.000 description 2
125000003302 alkenyloxy group Chemical group 0.000 description 2
125000004414 alkyl thio group Chemical group 0.000 description 2
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
235000010216 calcium carbonate Nutrition 0.000 description 2
239000012876 carrier material Substances 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
239000003085 diluting agent Substances 0.000 description 2
230000000694 effects Effects 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
239000012259 ether extract Substances 0.000 description 2
239000011737 fluorine Substances 0.000 description 2
229910052731 fluorine Inorganic materials 0.000 description 2
SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 2
TWBYWOBDOCUKOW-UHFFFAOYSA-N isonicotinic acid Chemical compound OC(=O)C1=CC=NC=C1 TWBYWOBDOCUKOW-UHFFFAOYSA-N 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
150000007522 mineralic acids Chemical class 0.000 description 2
125000001400 nonyl 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])C([H])([H])[H] 0.000 description 2
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 2
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
235000019260 propionic acid Nutrition 0.000 description 2
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 2
YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000011734 sodium Substances 0.000 description 2
239000012279 sodium borohydride Substances 0.000 description 2
229910000033 sodium borohydride Inorganic materials 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 1
MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 description 1
UWYVPFMHMJIBHE-OWOJBTEDSA-N (e)-2-hydroxybut-2-enedioic acid Chemical compound OC(=O)\C=C(\O)C(O)=O UWYVPFMHMJIBHE-OWOJBTEDSA-N 0.000 description 1
WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
NNMBNYHMJRJUBC-UHFFFAOYSA-N 1-bromo-3-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC(Br)=C1 NNMBNYHMJRJUBC-UHFFFAOYSA-N 0.000 description 1
QDFKKJYEIFBEFC-UHFFFAOYSA-N 1-bromo-3-fluorobenzene Chemical compound FC1=CC=CC(Br)=C1 QDFKKJYEIFBEFC-UHFFFAOYSA-N 0.000 description 1
WJIFKOVZNJTSGO-UHFFFAOYSA-N 1-bromo-3-methylbenzene Chemical compound CC1=CC=CC(Br)=C1 WJIFKOVZNJTSGO-UHFFFAOYSA-N 0.000 description 1
PKJBWOWQJHHAHG-UHFFFAOYSA-N 1-bromo-4-phenylbenzene Chemical group C1=CC(Br)=CC=C1C1=CC=CC=C1 PKJBWOWQJHHAHG-UHFFFAOYSA-N 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N 1-propanol Substances CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
RILZRCJGXSFXNE-UHFFFAOYSA-N 2-[4-(trifluoromethoxy)phenyl]ethanol Chemical compound OCCC1=CC=C(OC(F)(F)F)C=C1 RILZRCJGXSFXNE-UHFFFAOYSA-N 0.000 description 1
TUCRZHGAIRVWTI-UHFFFAOYSA-N 2-bromothiophene Chemical compound BrC1=CC=CS1 TUCRZHGAIRVWTI-UHFFFAOYSA-N 0.000 description 1
PKRSYEPBQPFNRB-UHFFFAOYSA-N 2-phenoxybenzoic acid Chemical compound OC(=O)C1=CC=CC=C1OC1=CC=CC=C1 PKRSYEPBQPFNRB-UHFFFAOYSA-N 0.000 description 1
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 description 1
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 1
125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 1
HJPKAXCCMTXNRO-UHFFFAOYSA-N 4-(3-azabicyclo[3.2.2]nonan-3-yl)-3-methylbutanenitrile Chemical compound C(#N)CC(CN1CC2CCC(C1)CC2)C HJPKAXCCMTXNRO-UHFFFAOYSA-N 0.000 description 1
ZJESVHHCOLPPSX-UHFFFAOYSA-N 4-(3-azabicyclo[3.2.2]nonan-3-yl)-3-methylbutanenitrile hydrochloride Chemical compound Cl.C(#N)CC(CN1CC2CCC(C1)CC2)C ZJESVHHCOLPPSX-UHFFFAOYSA-N 0.000 description 1
WUBBRNOQWQTFEX-UHFFFAOYSA-N 4-aminosalicylic acid Chemical compound NC1=CC=C(C(O)=O)C(O)=C1 WUBBRNOQWQTFEX-UHFFFAOYSA-N 0.000 description 1
TXYANRIJOVWJRK-UHFFFAOYSA-N 4-bromo-1-(4-bromo-2-phenylphenoxy)-2-phenylbenzene Chemical compound C=1C=CC=CC=1C1=CC(Br)=CC=C1OC1=CC=C(Br)C=C1C1=CC=CC=C1 TXYANRIJOVWJRK-UHFFFAOYSA-N 0.000 description 1
ZFCFBWSVQWGOJJ-UHFFFAOYSA-N 4-chlorobutanenitrile Chemical compound ClCCCC#N ZFCFBWSVQWGOJJ-UHFFFAOYSA-N 0.000 description 1
AEKVBBNGWBBYLL-UHFFFAOYSA-N 4-fluorobenzonitrile Chemical compound FC1=CC=C(C#N)C=C1 AEKVBBNGWBBYLL-UHFFFAOYSA-N 0.000 description 1
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
235000011437 Amygdalus communis Nutrition 0.000 description 1
BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
ZLZISLYKANBVNC-UHFFFAOYSA-N C(C=C/C(=O)O)(=O)O.CCCCCCCCC Chemical compound C(C=C/C(=O)O)(=O)O.CCCCCCCCC ZLZISLYKANBVNC-UHFFFAOYSA-N 0.000 description 1
OIJLOMUODOMYID-UHFFFAOYSA-M C12CN(CC(CC1)CC2)CCC[Mg]Cl Chemical compound C12CN(CC(CC1)CC2)CCC[Mg]Cl OIJLOMUODOMYID-UHFFFAOYSA-M 0.000 description 1
241000282472 Canis lupus familiaris Species 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
241000282693 Cercopithecidae Species 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 description 1
XWGUKRSIZIMSLT-UHFFFAOYSA-N Cl.C(#N)CCCN1CC2CCC(C1)CC2 Chemical compound Cl.C(#N)CCCN1CC2CCC(C1)CC2 XWGUKRSIZIMSLT-UHFFFAOYSA-N 0.000 description 1
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 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
YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 1
KIXRMCGTQHPFPF-UHFFFAOYSA-N FC1=CC=C(C=C1)C(CCCN1CC2CCC(C1)CC2)(C)O Chemical compound FC1=CC=C(C=C1)C(CCCN1CC2CCC(C1)CC2)(C)O KIXRMCGTQHPFPF-UHFFFAOYSA-N 0.000 description 1
241000282326 Felis catus Species 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
239000002841 Lewis acid Substances 0.000 description 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
238000003612 Meerwein-Ponndorf-Verley reduction reaction Methods 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
HSNVNALJRSJDHT-UHFFFAOYSA-N P(=O)(=O)[Mo] Chemical compound P(=O)(=O)[Mo] HSNVNALJRSJDHT-UHFFFAOYSA-N 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
241000220304 Prunus dulcis Species 0.000 description 1
239000007868 Raney catalyst Substances 0.000 description 1
229910000564 Raney nickel Inorganic materials 0.000 description 1
241000700159 Rattus Species 0.000 description 1
NACCJOIEZISYCU-UHFFFAOYSA-M [Br-].C1=CC([Mg+])=CC=C1C1=CC=CC=C1 Chemical compound [Br-].C1=CC([Mg+])=CC=C1C1=CC=CC=C1 NACCJOIEZISYCU-UHFFFAOYSA-M 0.000 description 1
NFSMTXPGEBBLLV-UHFFFAOYSA-M [Br-].CC1=CC=CC([Mg+])=C1 Chemical compound [Br-].CC1=CC=CC([Mg+])=C1 NFSMTXPGEBBLLV-UHFFFAOYSA-M 0.000 description 1
WSWOKFODOPIESP-UHFFFAOYSA-M [Br-].FC(F)(F)C1=CC=CC([Mg+])=C1 Chemical compound [Br-].FC(F)(F)C1=CC=CC([Mg+])=C1 WSWOKFODOPIESP-UHFFFAOYSA-M 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
150000008065 acid anhydrides Chemical class 0.000 description 1
239000013543 active substance Substances 0.000 description 1
229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
150000008041 alkali metal carbonates Chemical class 0.000 description 1
125000003342 alkenyl group Chemical group 0.000 description 1
150000004703 alkoxides Chemical class 0.000 description 1
125000005530 alkylenedioxy group Chemical group 0.000 description 1
235000020224 almond Nutrition 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
229910052782 aluminium Inorganic materials 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
229960004909 aminosalicylic acid Drugs 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
235000019730 animal feed additive Nutrition 0.000 description 1
150000001450 anions Chemical class 0.000 description 1
230000003276 anti-hypertensive effect Effects 0.000 description 1
125000004104 aryloxy group Chemical group 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
229910052788 barium Inorganic materials 0.000 description 1
DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
229940092714 benzenesulfonic acid Drugs 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
125000001246 bromo group Chemical group Br* 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
239000000920 calcium hydroxide Substances 0.000 description 1
229910001861 calcium hydroxide Inorganic materials 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
229940117975 chromium trioxide Drugs 0.000 description 1
WGLPBDUCMAPZCE-UHFFFAOYSA-N chromium trioxide Inorganic materials O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 1
GAMDZJFZMJECOS-UHFFFAOYSA-N chromium(6+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Cr+6] GAMDZJFZMJECOS-UHFFFAOYSA-N 0.000 description 1
235000013985 cinnamic acid Nutrition 0.000 description 1
229930016911 cinnamic acid Natural products 0.000 description 1
HNEGQIOMVPPMNR-IHWYPQMZSA-N citraconic acid Chemical compound OC(=O)C(/C)=C\C(O)=O HNEGQIOMVPPMNR-IHWYPQMZSA-N 0.000 description 1
235000015165 citric acid Nutrition 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
239000010949 copper Substances 0.000 description 1
JGDFBJMWFLXCLJ-UHFFFAOYSA-N copper chromite Chemical compound [Cu]=O.[Cu]=O.O=[Cr]O[Cr]=O JGDFBJMWFLXCLJ-UHFFFAOYSA-N 0.000 description 1
150000008049 diazo compounds Chemical class 0.000 description 1
WLXALCKAKGDNAT-UHFFFAOYSA-N diazoethane Chemical compound CC=[N+]=[N-] WLXALCKAKGDNAT-UHFFFAOYSA-N 0.000 description 1
125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
239000003814 drug Substances 0.000 description 1
230000032050 esterification Effects 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
AFAXGSQYZLGZPG-UHFFFAOYSA-N ethanedisulfonic acid Chemical compound OS(=O)(=O)CCS(O)(=O)=O AFAXGSQYZLGZPG-UHFFFAOYSA-N 0.000 description 1
CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
238000006266 etherification reaction Methods 0.000 description 1
MDKXBBPLEGPIRI-UHFFFAOYSA-N ethoxyethane;methanol Chemical compound OC.CCOCC MDKXBBPLEGPIRI-UHFFFAOYSA-N 0.000 description 1
YKWNUSJLICDQEO-UHFFFAOYSA-N ethoxyethane;propan-2-ol Chemical compound CC(C)O.CCOCC YKWNUSJLICDQEO-UHFFFAOYSA-N 0.000 description 1
QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
235000011087 fumaric acid Nutrition 0.000 description 1
125000002541 furyl group Chemical group 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
229940093915 gynecological organic acid Drugs 0.000 description 1
125000005842 heteroatom Chemical group 0.000 description 1
QMEZUZOCLYUADC-UHFFFAOYSA-N hydrate;dihydrochloride Chemical compound O.Cl.Cl QMEZUZOCLYUADC-UHFFFAOYSA-N 0.000 description 1
150000004677 hydrates Chemical class 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
229910000042 hydrogen bromide Inorganic materials 0.000 description 1
239000000852 hydrogen donor Substances 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
150000002561 ketenes Chemical class 0.000 description 1
150000007517 lewis acids Chemical class 0.000 description 1
239000007788 liquid Substances 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
239000012280 lithium aluminium hydride Substances 0.000 description 1
IHLVCKWPAMTVTG-UHFFFAOYSA-N lithium;carbanide Chemical compound [Li+].[CH3-] IHLVCKWPAMTVTG-UHFFFAOYSA-N 0.000 description 1
HTJPDOPKPWUNBX-UHFFFAOYSA-M magnesium;2h-thiophen-2-ide;bromide Chemical compound [Mg+2].[Br-].C=1C=[C-]SC=1 HTJPDOPKPWUNBX-UHFFFAOYSA-M 0.000 description 1
DTKMKZYEOXZPQZ-UHFFFAOYSA-M magnesium;fluorobenzene;bromide Chemical compound [Mg+2].[Br-].FC1=CC=C[C-]=C1 DTKMKZYEOXZPQZ-UHFFFAOYSA-M 0.000 description 1
MPMNUCMJDPWNCV-UHFFFAOYSA-M magnesium;phenoxybenzene;bromide Chemical compound [Mg+2].[Br-].C=1C=[C-]C=CC=1OC1=CC=CC=C1 MPMNUCMJDPWNCV-UHFFFAOYSA-M 0.000 description 1
239000001630 malic acid Substances 0.000 description 1
235000011090 malic acid Nutrition 0.000 description 1
229960002510 mandelic acid Drugs 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
229910000000 metal hydroxide Inorganic materials 0.000 description 1
150000004692 metal hydroxides Chemical class 0.000 description 1
UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
KVBGVZZKJNLNJU-UHFFFAOYSA-N naphthalene-2-sulfonic acid Chemical compound C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-N 0.000 description 1
229910052759 nickel Inorganic materials 0.000 description 1
239000011664 nicotinic acid Substances 0.000 description 1
229960003512 nicotinic acid Drugs 0.000 description 1
235000001968 nicotinic acid Nutrition 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
150000002902 organometallic compounds Chemical class 0.000 description 1
MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
XSKIUFGOTYHDLC-UHFFFAOYSA-N palladium rhodium Chemical compound [Rh].[Pd] XSKIUFGOTYHDLC-UHFFFAOYSA-N 0.000 description 1
FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
235000011007 phosphoric acid Nutrition 0.000 description 1
150000003016 phosphoric acids Chemical class 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
229910003446 platinum oxide Inorganic materials 0.000 description 1
235000007686 potassium Nutrition 0.000 description 1
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
230000001003 psychopharmacologic effect Effects 0.000 description 1
238000000746 purification Methods 0.000 description 1
239000002994 raw material Substances 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
229960004889 salicylic acid Drugs 0.000 description 1
239000000932 sedative agent Substances 0.000 description 1
230000001624 sedative effect Effects 0.000 description 1
235000015424 sodium Nutrition 0.000 description 1
GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
239000001384 succinic acid Substances 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
125000004434 sulfur atom Chemical group 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000001302 tertiary amino group Chemical group 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
125000003396 thiol group Chemical group [H]S* 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
- 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
- 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
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/08—Bridged systems

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Epidemiology (AREA)
Medicinal Chemistry (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Indole Compounds (AREA)

CH1673468A 1966-07-27 1966-07-27 Verfahren zur Herstellung neuer azabicycloaliphatischer Verbindungen CH507947A (de)

Priority Applications (9)

Application Number	Priority Date	Filing Date	Title
CH1673568A CH486463A (de)	1966-07-27	1966-07-27	Verfahren zur Herstellung neuer azabicycloaliphatischer Verbindungen
CH1088966A CH508626A (de)	1966-07-27	1966-07-27	Verfahren zur Herstellung neuer azabicycloaliphatischer Verbindungen
CH1673468A CH507947A (de)	1966-07-27	1966-07-27	Verfahren zur Herstellung neuer azabicycloaliphatischer Verbindungen
DE1967C0042904 DE1670448B2 (de)	1966-07-27	1967-07-19	3-eckige klammer auf 4-(4-fluorphenyl)- 4-oxo-1-n-butyl eckige klammer zu -3-aza- bicyclo eckige klammer auf 3,2,2 eckige klammer zu nonan, dessen salze, verfahren zu deren herstellung und arzneimittel
FR1549235D FR1549235A (fr)	1966-07-27	1967-07-20
GB33851/67A GB1195729A (en)	1966-07-27	1967-07-24	Azabicycloaliphatic Compounds
BE701861D BE701861A (fr)	1966-07-27	1967-07-26
FR124193A FR7320M (fr)	1966-07-27	1967-10-12
FR124194A FR7074M (fr)	1966-07-27	1967-10-12

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
CH1673568A CH486463A (de)	1966-07-27	1966-07-27	Verfahren zur Herstellung neuer azabicycloaliphatischer Verbindungen
CH1088966A CH508626A (de)	1966-07-27	1966-07-27	Verfahren zur Herstellung neuer azabicycloaliphatischer Verbindungen
CH1673468A CH507947A (de)	1966-07-27	1966-07-27	Verfahren zur Herstellung neuer azabicycloaliphatischer Verbindungen
CH799267		1967-06-06

Publications (1)

Publication Number	Publication Date
CH507947A true CH507947A (de)	1971-05-31

Family

ID=27429116

Family Applications (3)

Application Number	Title	Priority Date	Filing Date
CH1673468A CH507947A (de)	1966-07-27	1966-07-27	Verfahren zur Herstellung neuer azabicycloaliphatischer Verbindungen
CH1673568A CH486463A (de)	1966-07-27	1966-07-27	Verfahren zur Herstellung neuer azabicycloaliphatischer Verbindungen
CH1088966A CH508626A (de)	1966-07-27	1966-07-27	Verfahren zur Herstellung neuer azabicycloaliphatischer Verbindungen

Family Applications After (2)

Application Number	Title	Priority Date	Filing Date
CH1673568A CH486463A (de)	1966-07-27	1966-07-27	Verfahren zur Herstellung neuer azabicycloaliphatischer Verbindungen
CH1088966A CH508626A (de)	1966-07-27	1966-07-27	Verfahren zur Herstellung neuer azabicycloaliphatischer Verbindungen

Country Status (5)

Country	Link
BE (1)	BE701861A (fr)
CH (3)	CH507947A (fr)
DE (1)	DE1670448B2 (fr)
FR (2)	FR1549235A (fr)
GB (1)	GB1195729A (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3843481A1 (de) *	1988-12-23	1990-06-28	Boehringer Ingelheim Kg	Substituierte 3-azabicyclo/3.1.1/heptane, ihre herstellung und ihre verwendung
NZ513575A (en) *	1999-05-04	2003-07-25	Neurosearch As	Heteroaryl diazabicycloalkanes useful for treating or preventing a disease or a disorder responsive to the activity of nAChR modulators

1966
- 1966-07-27 CH CH1673468A patent/CH507947A/de not_active IP Right Cessation
- 1966-07-27 CH CH1673568A patent/CH486463A/de not_active IP Right Cessation
- 1966-07-27 CH CH1088966A patent/CH508626A/de not_active IP Right Cessation
1967
- 1967-07-19 DE DE1967C0042904 patent/DE1670448B2/de active Granted
- 1967-07-20 FR FR1549235D patent/FR1549235A/fr not_active Expired
- 1967-07-24 GB GB33851/67A patent/GB1195729A/en not_active Expired
- 1967-07-26 BE BE701861D patent/BE701861A/xx unknown
- 1967-10-12 FR FR124194A patent/FR7074M/fr not_active Expired

Also Published As

Publication number	Publication date
BE701861A (fr)	1968-01-26
FR1549235A (fr)	1968-12-13
GB1195729A (en)	1970-06-24
CH508626A (de)	1971-06-15
DE1670448A1 (de)	1971-02-11
CH486463A (de)	1970-02-28
FR7074M (fr)	1969-06-30
DE1670448B2 (de)	1976-09-02

Legal Events

Date	Code	Title	Description
1984-03-30	PL	Patent ceased

Publication	Publication Date	Title
DE69328975T2 (de)	2000-11-09	Aminomethylen substituierte heterocyclische verbindungen und ihre verwendung alssubstanz p antagonisten
DE60008262T2 (de)	2004-12-16	Piperazinderivate als 5-ht1b antagonisten
DE69232099T2 (de)	2002-06-06	1,3-substituierte cycloalkene und cycloalkane mit zentraler nervensystemwirkung
DE2047658B2 (de)	1980-03-20	2-Styryl- und 2-Phenyläthinylbenzylaminderivate, Verfahren zu deren Herstellung und diese enthaltende Arzneimittel
CH623584A5 (fr)	1981-06-15
DE1518975A1 (de)	1969-09-11	Verfahren zur Herstellung von Dibenzocycloheptatrien- Verbindungen
EP0389425B1 (fr)	1995-04-26	Benzothiopyranylamines
DE2653147C2 (fr)	1991-09-19
CH619683A5 (fr)	1980-10-15
DE2653251A1 (de)	1977-06-08	Azabicyclo eckige klammer auf 3.1.o eckige klammer zu hexan-derivate, ihre herstellung und verwendung
DE2626583A1 (de)	1977-01-13	Neue benzocycloheptathiophenderivate ihre herstellung und ihre verwendung als heilmittel
AT273985B (de)	1969-09-10	Verfahren zur Herstellung von neuen azabicycloaliphatischen Verbindungen und ihren Salzen
DE2349493A1 (de)	1974-04-18	2-(2-pyridyl)- omega-phenylalkylamine und verfahren zu ihrer herstellung
DE2431201A1 (de)	1975-01-16	4-aryldecahydro-1h-pyrrolo eckige klammer auf 3,4-f eckige klammer zu chinolinderivate, verfahren zu ihrer herstellung und arzneimittel
DE2160911A1 (de)	1972-08-10	Verfahren zur Herstellung von Aminoketonen
DE3209271A1 (de)	1983-09-15	Bicyclische phenolether, verfahren zu deren herstellung sowie diese verbindungen enthaltende arzneimittel
DE2235667A1 (de)	1973-03-01	Hexahydrobenz/e/indolderivate
DE2261269B2 (de)	1979-10-18	1- [4-(p-Fluorphenyl)-4-oxo-2-butenyl] -4-phenyl-4hydroxypiperidin-Derivate
CH535767A (de)	1973-04-15	Verfahren zur Herstellung neuer N-Phenäthylpiperidinderivate
DE1643325B2 (de)	1976-05-06	3-aminoacylaminothiophene und verfahren zu ihrer herstellung
AT375079B (de)	1984-06-25	Verfahren zur herstellung von neuen trans-2,3,4,4a ,5,9b-hexahydro-1h-pyrido(4,3-b)indolen und ihren pharmazeutisch annehmbaren salzen
AT355038B (de)	1980-02-11	Verfahren zur herstellung von neuen veraetherten hydroxy-benzimidazolonen, -benzoxazolonen, - -benzoxazinonen, -chinazolinonen und- chino- xazolinonen
AT363094B (de)	1981-07-10	Verfahren zur herstellung von neuen piperazinderivaten und deren salzen
AT372957B (de)	1983-12-12	Verfahren zur herstellung von neuen 5-subst.-10,11-dihydro-5h-dibenzo(a,d)-cyclohep en-5,10-iminen und von deren salzen sowie optischen isomeren
AT330372B (de)	1976-06-25	Verfahren zur herstellung von neuen 2- (heteroaryl-methyl) -5,9beta-dialkyl -6,7- benzomorphanen