CH617938A5 - - Google Patents

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Publication number: CH617938A5
Authority: CH; Switzerland
Prior art keywords: formula; group; compound; carbon atoms; phr
Prior art date: 1973-12-12

Application number

CH1647074A

Other languages

German (de)

English (en)

Inventor

Victor John Bauer

Raymond Walter Kosley Jr

Original Assignee

Hoechst 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.)

1973-12-12

Filing date

1974-12-11

Publication date

1980-06-30

1974-12-11 Application filed by Hoechst Ag filed Critical Hoechst Ag

1980-06-30 Publication of CH617938A5 publication Critical patent/CH617938A5/de

Links

150000001875 compounds Chemical class 0.000 claims description 76
125000004432 carbon atom Chemical group C* 0.000 claims description 57
238000000034 method Methods 0.000 claims description 48
LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 32
125000000217 alkyl group Chemical group 0.000 claims description 24
229910052739 hydrogen Inorganic materials 0.000 claims description 24
239000001257 hydrogen Substances 0.000 claims description 24
239000002253 acid Substances 0.000 claims description 22
-1 methylene-dioxy group Chemical group 0.000 claims description 18
238000006243 chemical reaction Methods 0.000 claims description 16
150000002431 hydrogen Chemical group 0.000 claims description 16
125000003545 alkoxy group Chemical group 0.000 claims description 14
125000002252 acyl group Chemical group 0.000 claims description 10
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 10
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 10
125000003884 phenylalkyl group Chemical group 0.000 claims description 10
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
238000002360 preparation method Methods 0.000 claims description 9
150000003839 salts Chemical class 0.000 claims description 9
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
239000007818 Grignard reagent Substances 0.000 claims description 6
125000003342 alkenyl group Chemical group 0.000 claims description 6
125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 6
125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims description 6
125000000753 cycloalkyl group Chemical group 0.000 claims description 6
238000005661 deetherification reaction Methods 0.000 claims description 6
150000004795 grignard reagents Chemical class 0.000 claims description 6
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
230000010933 acylation Effects 0.000 claims description 5
238000005917 acylation reaction Methods 0.000 claims description 5
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 4
JTXAETLSYPFRJX-UHFFFAOYSA-N [Li]C1=C(C=CC=C1)C=1OCCN1 Chemical compound [Li]C1=C(C=CC=C1)C=1OCCN1 JTXAETLSYPFRJX-UHFFFAOYSA-N 0.000 claims description 4
239000003153 chemical reaction reagent Substances 0.000 claims description 4
229910052736 halogen Inorganic materials 0.000 claims description 4
150000002367 halogens Chemical class 0.000 claims description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
239000011777 magnesium Substances 0.000 claims description 4
229910052749 magnesium Inorganic materials 0.000 claims description 4
125000002524 organometallic group Chemical group 0.000 claims description 4
241000251730 Chondrichthyes Species 0.000 claims description 3
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
230000029936 alkylation Effects 0.000 claims description 3
238000005804 alkylation reaction Methods 0.000 claims description 3
239000012024 dehydrating agents‎ Substances 0.000 claims description 3
238000005984 hydrogenation reaction Methods 0.000 claims description 3
229910052744 lithium Inorganic materials 0.000 claims description 3
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 claims description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 2
230000002378 acidificating effect Effects 0.000 claims description 2
125000001931 aliphatic group Chemical group 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims description 2
150000003254 radicals Chemical class 0.000 claims description 2
238000006555 catalytic reaction Methods 0.000 claims 1
229910052757 nitrogen Inorganic materials 0.000 claims 1
125000004433 nitrogen atom Chemical group N* 0.000 claims 1
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 34
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 34
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 30
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 30
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
238000002844 melting Methods 0.000 description 22
230000008018 melting Effects 0.000 description 22
239000013078 crystal Substances 0.000 description 20
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
239000000203 mixture Substances 0.000 description 18
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 17
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 17
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 16
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
238000010992 reflux Methods 0.000 description 12
239000002904 solvent Substances 0.000 description 12
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 11
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 11
229910000041 hydrogen chloride Inorganic materials 0.000 description 11
238000001953 recrystallisation Methods 0.000 description 10
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 10
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
229910000027 potassium carbonate Inorganic materials 0.000 description 8
239000007787 solid Substances 0.000 description 8
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
241000699670 Mus sp. Species 0.000 description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
229960000583 acetic acid Drugs 0.000 description 6
229910052938 sodium sulfate Inorganic materials 0.000 description 6
235000011152 sodium sulphate Nutrition 0.000 description 6
RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 6
235000011054 acetic acid Nutrition 0.000 description 5
239000012280 lithium aluminium hydride Substances 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
238000003756 stirring Methods 0.000 description 5
239000000126 substance Substances 0.000 description 5
238000012360 testing method Methods 0.000 description 5
NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 5
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 4
241000124008 Mammalia Species 0.000 description 4
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
239000003054 catalyst Substances 0.000 description 4
239000000460 chlorine Substances 0.000 description 4
229910000042 hydrogen bromide Inorganic materials 0.000 description 4
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 4
239000000047 product Substances 0.000 description 4
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 3
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
239000002168 alkylating agent Substances 0.000 description 3
229940100198 alkylating agent Drugs 0.000 description 3
230000000202 analgesic effect Effects 0.000 description 3
230000001430 anti-depressive effect Effects 0.000 description 3
239000000935 antidepressant agent Substances 0.000 description 3
229940005513 antidepressants Drugs 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
238000010438 heat treatment Methods 0.000 description 3
239000000463 material Substances 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
239000012279 sodium borohydride Substances 0.000 description 3
229910000033 sodium borohydride Inorganic materials 0.000 description 3
239000000725 suspension Substances 0.000 description 3
239000003204 tranquilizing agent Substances 0.000 description 3
230000002936 tranquilizing effect Effects 0.000 description 3
KWTSXDURSIMDCE-QMMMGPOBSA-N (S)-amphetamine Chemical compound C[C@H](N)CC1=CC=CC=C1 KWTSXDURSIMDCE-QMMMGPOBSA-N 0.000 description 2
ZFJQWOMHWFYLPD-UHFFFAOYSA-N 1-phenylspiro[1h-2-benzofuran-3,4'-piperidine] Chemical compound C1CNCCC21C1=CC=CC=C1C(C=1C=CC=CC=1)O2 ZFJQWOMHWFYLPD-UHFFFAOYSA-N 0.000 description 2
XRXMNWGCKISMOH-UHFFFAOYSA-N 2-bromobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1Br XRXMNWGCKISMOH-UHFFFAOYSA-N 0.000 description 2
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 2
ICMJMKOIRYHDBC-UHFFFAOYSA-N 4-[2-(4,4-dimethyl-5h-1,3-oxazol-2-yl)phenyl]-1-methylpiperidin-4-ol Chemical compound C1CN(C)CCC1(O)C1=CC=CC=C1C1=NC(C)(C)CO1 ICMJMKOIRYHDBC-UHFFFAOYSA-N 0.000 description 2
CZKLEJHVLCMVQR-UHFFFAOYSA-N 4-fluorobenzoyl chloride Chemical compound FC1=CC=C(C(Cl)=O)C=C1 CZKLEJHVLCMVQR-UHFFFAOYSA-N 0.000 description 2
OYXDDESRPMPNMQ-UHFFFAOYSA-N 5-methoxy-1'-methyl-1-phenylspiro[1h-2-benzofuran-3,4'-piperidine] Chemical compound C12=CC(OC)=CC=C2C(C=2C=CC=CC=2)OC21CCN(C)CC2 OYXDDESRPMPNMQ-UHFFFAOYSA-N 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
0 C[C@](*=C)(C=C1)C#CC(*2=CC2)=C1C1=NC(*)(*)CO1 Chemical compound C[C@](*=C)(C=C1)C#CC(*2=CC2)=C1C1=NC(*)(*)CO1 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
238000005863 Friedel-Crafts acylation reaction Methods 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
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 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
229940025084 amphetamine Drugs 0.000 description 2
229940035676 analgesics Drugs 0.000 description 2
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
239000000730 antalgic agent Substances 0.000 description 2
PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 2
230000037396 body weight Effects 0.000 description 2
210000003169 central nervous system Anatomy 0.000 description 2
239000003638 chemical reducing agent Substances 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
238000000354 decomposition reaction Methods 0.000 description 2
230000000694 effects Effects 0.000 description 2
DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
239000005457 ice water Substances 0.000 description 2
BRKADVNLTRCLOW-UHFFFAOYSA-M magnesium;fluorobenzene;bromide Chemical compound [Mg+2].[Br-].FC1=CC=[C-]C=C1 BRKADVNLTRCLOW-UHFFFAOYSA-M 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
239000012299 nitrogen atmosphere Substances 0.000 description 2
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
239000012258 stirred mixture Substances 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
230000001988 toxicity Effects 0.000 description 2
231100000419 toxicity Toxicity 0.000 description 2
LJHMEWBXTMUWBK-UHFFFAOYSA-N (2-bromo-4,5-dimethoxyphenyl)-phenylmethanol Chemical compound C1=C(OC)C(OC)=CC(Br)=C1C(O)C1=CC=CC=C1 LJHMEWBXTMUWBK-UHFFFAOYSA-N 0.000 description 1
QCMQYFUIIQLFJC-UHFFFAOYSA-N (2-bromo-4,5-dimethoxyphenyl)-phenylmethanone Chemical compound C1=C(OC)C(OC)=CC(Br)=C1C(=O)C1=CC=CC=C1 QCMQYFUIIQLFJC-UHFFFAOYSA-N 0.000 description 1
DCQUBBDIPZQYBK-UHFFFAOYSA-N (2-bromo-4-fluorophenyl)-(4-fluorophenyl)methanol Chemical compound C=1C=C(F)C=C(Br)C=1C(O)C1=CC=C(F)C=C1 DCQUBBDIPZQYBK-UHFFFAOYSA-N 0.000 description 1
PVOOOEKGGXYVAL-UHFFFAOYSA-N (2-bromo-4-fluorophenyl)-(4-fluorophenyl)methanone Chemical compound C1=CC(F)=CC=C1C(=O)C1=CC=C(F)C=C1Br PVOOOEKGGXYVAL-UHFFFAOYSA-N 0.000 description 1
RRMGEXJZWUCSHO-UHFFFAOYSA-N (2-bromo-4-fluorophenyl)-phenylmethanol Chemical compound C=1C=C(F)C=C(Br)C=1C(O)C1=CC=CC=C1 RRMGEXJZWUCSHO-UHFFFAOYSA-N 0.000 description 1
MMIDQHSATXDLNV-UHFFFAOYSA-N (2-bromo-4-fluorophenyl)-phenylmethanone Chemical compound BrC1=CC(F)=CC=C1C(=O)C1=CC=CC=C1 MMIDQHSATXDLNV-UHFFFAOYSA-N 0.000 description 1
ACXQDSLHHPKHAW-UHFFFAOYSA-N (2-bromo-4-methoxyphenyl)-(4-fluorophenyl)methanone Chemical compound BrC1=CC(OC)=CC=C1C(=O)C1=CC=C(F)C=C1 ACXQDSLHHPKHAW-UHFFFAOYSA-N 0.000 description 1
VWOCMJRHJKFMKS-UHFFFAOYSA-N (2-bromo-4-methoxyphenyl)-phenylmethanol Chemical compound BrC1=CC(OC)=CC=C1C(O)C1=CC=CC=C1 VWOCMJRHJKFMKS-UHFFFAOYSA-N 0.000 description 1
YRSMISMMWHKCAL-UHFFFAOYSA-N (2-bromo-4-methoxyphenyl)-phenylmethanone Chemical compound BrC1=CC(OC)=CC=C1C(=O)C1=CC=CC=C1 YRSMISMMWHKCAL-UHFFFAOYSA-N 0.000 description 1
HOFSDZGFRKDXAD-UHFFFAOYSA-N (2-bromo-4-methylphenyl)-phenylmethanol Chemical compound BrC1=CC(C)=CC=C1C(O)C1=CC=CC=C1 HOFSDZGFRKDXAD-UHFFFAOYSA-N 0.000 description 1
INTFJDJHLDMTQN-UHFFFAOYSA-N (2-bromo-5-chlorophenyl)-phenylmethanol Chemical compound C=1C(Cl)=CC=C(Br)C=1C(O)C1=CC=CC=C1 INTFJDJHLDMTQN-UHFFFAOYSA-N 0.000 description 1
MKCLVAZPKSCYQH-UHFFFAOYSA-N (2-bromo-5-chlorophenyl)-phenylmethanone Chemical compound ClC1=CC=C(Br)C(C(=O)C=2C=CC=CC=2)=C1 MKCLVAZPKSCYQH-UHFFFAOYSA-N 0.000 description 1
DDULRUPNYFZANK-UHFFFAOYSA-N (2-bromophenyl)-(2-methylphenyl)methanol Chemical compound CC1=CC=CC=C1C(O)C1=CC=CC=C1Br DDULRUPNYFZANK-UHFFFAOYSA-N 0.000 description 1
HWOKKPHUCIWPRO-UHFFFAOYSA-N (2-bromophenyl)-(3,4-dimethoxyphenyl)methanol Chemical compound C1=C(OC)C(OC)=CC=C1C(O)C1=CC=CC=C1Br HWOKKPHUCIWPRO-UHFFFAOYSA-N 0.000 description 1
FNOLIQBFMNUMST-UHFFFAOYSA-N (2-bromophenyl)-(3-fluorophenyl)methanol Chemical compound C=1C=CC=C(Br)C=1C(O)C1=CC=CC(F)=C1 FNOLIQBFMNUMST-UHFFFAOYSA-N 0.000 description 1
XZRDCSRAGROTPK-UHFFFAOYSA-N (2-bromophenyl)-(4-chlorophenyl)methanol Chemical compound C=1C=CC=C(Br)C=1C(O)C1=CC=C(Cl)C=C1 XZRDCSRAGROTPK-UHFFFAOYSA-N 0.000 description 1
BSDDNYJEIVCQEZ-UHFFFAOYSA-N (2-bromophenyl)-(4-fluorophenyl)methanol Chemical compound C=1C=CC=C(Br)C=1C(O)C1=CC=C(F)C=C1 BSDDNYJEIVCQEZ-UHFFFAOYSA-N 0.000 description 1
WSGPNOCUUSZBHY-UHFFFAOYSA-N (2-bromophenyl)-(4-methoxyphenyl)methanol Chemical compound C1=CC(OC)=CC=C1C(O)C1=CC=CC=C1Br WSGPNOCUUSZBHY-UHFFFAOYSA-N 0.000 description 1
JOXJJOHFXZJYAK-UHFFFAOYSA-N (2-bromophenyl)-(4-methylphenyl)methanol Chemical compound C1=CC(C)=CC=C1C(O)C1=CC=CC=C1Br JOXJJOHFXZJYAK-UHFFFAOYSA-N 0.000 description 1
RTCLKVCTCLNTDY-UHFFFAOYSA-N (2-bromophenyl)-[4-(trifluoromethyl)phenyl]methanol Chemical compound C=1C=CC=C(Br)C=1C(O)C1=CC=C(C(F)(F)F)C=C1 RTCLKVCTCLNTDY-UHFFFAOYSA-N 0.000 description 1
ABEVIHIQUUXDMS-UHFFFAOYSA-N (2-bromophenyl)-phenylmethanone Chemical compound BrC1=CC=CC=C1C(=O)C1=CC=CC=C1 ABEVIHIQUUXDMS-UHFFFAOYSA-N 0.000 description 1
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WXUIBLFRXIIFRP-UHFFFAOYSA-N (6-bromo-1,3-benzodioxol-5-yl)-phenylmethanol Chemical compound C=1C=2OCOC=2C=C(Br)C=1C(O)C1=CC=CC=C1 WXUIBLFRXIIFRP-UHFFFAOYSA-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
CMGBHCCDZXPUIG-UHFFFAOYSA-N 1'-methyl-1-phenylspiro[1h-2-benzofuran-3,4'-piperidine] Chemical compound C1CN(C)CCC21C1=CC=CC=C1C(C=1C=CC=CC=1)O2 CMGBHCCDZXPUIG-UHFFFAOYSA-N 0.000 description 1
PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 1
FDXJBZASIMJWRO-UHFFFAOYSA-N 1,3-benzodioxol-5-yl-(2-bromophenyl)methanol Chemical compound C=1C=C2OCOC2=CC=1C(O)C1=CC=CC=C1Br FDXJBZASIMJWRO-UHFFFAOYSA-N 0.000 description 1
JABMXOHZXFJZBF-UHFFFAOYSA-N 1-(2-bromophenyl)-1-phenylethanol Chemical compound C=1C=CC=C(Br)C=1C(O)(C)C1=CC=CC=C1 JABMXOHZXFJZBF-UHFFFAOYSA-N 0.000 description 1
JFWWJFRTGUIZEA-UHFFFAOYSA-N 1-(4-fluorophenyl)spiro[1h-2-benzofuran-3,4'-piperidine] Chemical compound C1=CC(F)=CC=C1C1C2=CC=CC=C2C2(CCNCC2)O1 JFWWJFRTGUIZEA-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
PLDWAJLZAAHOGG-UHFFFAOYSA-N 1-bromo-3-methoxybenzene Chemical compound COC1=CC=CC(Br)=C1 PLDWAJLZAAHOGG-UHFFFAOYSA-N 0.000 description 1
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NLHIYWSPOVJSTB-UHFFFAOYSA-N 1-phenyl-3-(1-phenylspiro[1h-2-benzofuran-3,4'-piperidine]-1'-yl)propan-1-ol Chemical compound C=1C=CC=CC=1C(O)CCN(CC1)CCC1(C1=CC=CC=C11)OC1C1=CC=CC=C1 NLHIYWSPOVJSTB-UHFFFAOYSA-N 0.000 description 1
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125000006197 2-benzoyl ethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(=O)C([H])([H])C([H])([H])* 0.000 description 1
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BIANZVZZKGIQKG-UHFFFAOYSA-N 4-[4-(5-hydroxypentoxy)phenyl]benzonitrile Chemical compound C1=CC(OCCCCCO)=CC=C1C1=CC=C(C#N)C=C1 BIANZVZZKGIQKG-UHFFFAOYSA-N 0.000 description 1
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 1
125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
KASOQGOEIYDSMF-UHFFFAOYSA-N 5-fluoro-1-(4-fluorophenyl)spiro[1h-2-benzofuran-3,4'-piperidine] Chemical compound C1=CC(F)=CC=C1C1C2=CC=C(F)C=C2C2(CCNCC2)O1 KASOQGOEIYDSMF-UHFFFAOYSA-N 0.000 description 1
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OMIHGPLIXGGMJB-UHFFFAOYSA-N 7-oxabicyclo[4.1.0]hepta-1,3,5-triene Chemical compound C1=CC=C2OC2=C1 OMIHGPLIXGGMJB-UHFFFAOYSA-N 0.000 description 1
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BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
CDEMHJCJMMOFMB-UHFFFAOYSA-M ClC1=CC=C([Mg]Br)C=C1 Chemical compound ClC1=CC=C([Mg]Br)C=C1 CDEMHJCJMMOFMB-UHFFFAOYSA-M 0.000 description 1
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239000013543 active substance Substances 0.000 description 1
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PQLAYKMGZDUDLQ-UHFFFAOYSA-K aluminium bromide Chemical compound Br[Al](Br)Br PQLAYKMGZDUDLQ-UHFFFAOYSA-K 0.000 description 1
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CBTVGIZVANVGBH-UHFFFAOYSA-N aminomethyl propanol Chemical compound CC(C)(N)CO CBTVGIZVANVGBH-UHFFFAOYSA-N 0.000 description 1
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239000000969 carrier Substances 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
239000012320 chlorinating reagent Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
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WGLPBDUCMAPZCE-UHFFFAOYSA-N chromium trioxide Inorganic materials O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 1
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238000001816 cooling Methods 0.000 description 1
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239000002552 dosage form Substances 0.000 description 1
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239000011737 fluorine Substances 0.000 description 1
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235000019253 formic acid Nutrition 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
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150000004820 halides Chemical class 0.000 description 1
150000002440 hydroxy compounds Chemical class 0.000 description 1
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239000012442 inert solvent Substances 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
230000000977 initiatory effect Effects 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical class II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
239000011630 iodine Substances 0.000 description 1
150000007517 lewis acids Chemical class 0.000 description 1
239000007788 liquid Substances 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
VXWPONVCMVLXBW-UHFFFAOYSA-M magnesium;carbanide;iodide Chemical compound [CH3-].[Mg+2].[I-] VXWPONVCMVLXBW-UHFFFAOYSA-M 0.000 description 1
BVUQKCCKUOSAEV-UHFFFAOYSA-M magnesium;methylbenzene;bromide Chemical compound [Mg+2].[Br-].CC1=CC=[C-]C=C1 BVUQKCCKUOSAEV-UHFFFAOYSA-M 0.000 description 1
YAMQOOCGNXAQGW-UHFFFAOYSA-M magnesium;methylbenzene;bromide Chemical compound [Mg+2].[Br-].CC1=CC=CC=[C-]1 YAMQOOCGNXAQGW-UHFFFAOYSA-M 0.000 description 1
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239000000155 melt Substances 0.000 description 1
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
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150000007522 mineralic acids Chemical class 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
230000036640 muscle relaxation Effects 0.000 description 1
229930014626 natural product Natural products 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
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238000007254 oxidation reaction Methods 0.000 description 1
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238000004806 packaging method and process Methods 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
AHWALFGBDFAJAI-UHFFFAOYSA-N phenyl carbonochloridate Chemical compound ClC(=O)OC1=CC=CC=C1 AHWALFGBDFAJAI-UHFFFAOYSA-N 0.000 description 1
NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 1
ANRQGKOBLBYXFM-UHFFFAOYSA-M phenylmagnesium bromide Chemical compound Br[Mg]C1=CC=CC=C1 ANRQGKOBLBYXFM-UHFFFAOYSA-M 0.000 description 1
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
230000002265 prevention Effects 0.000 description 1
201000003004 ptosis Diseases 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
239000000376 reactant Substances 0.000 description 1
230000011514 reflex Effects 0.000 description 1
230000035939 shock Effects 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000012419 sodium bis(2-methoxyethoxy)aluminum hydride Substances 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
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QJDUDPQVDAASMV-UHFFFAOYSA-M sodium;ethanethiolate Chemical compound [Na+].CC[S-] QJDUDPQVDAASMV-UHFFFAOYSA-M 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
229960001367 tartaric acid Drugs 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
229940125725 tranquilizer Drugs 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D263/10—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
- C07C43/14—Unsaturated ethers
- C07C43/17—Unsaturated ethers containing halogen
- C07C43/174—Unsaturated ethers containing halogen containing six-membered aromatic rings
- C07C43/1742—Unsaturated ethers containing halogen containing six-membered aromatic rings with halogen atoms bound to the aromatic rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/28—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of CHx-moieties
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
- C07C45/46—Friedel-Crafts reactions
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/38—Unsaturated compounds having —CHO groups bound to carbon atoms of rings other than six—membered aromatic rings
- C07C47/45—Unsaturated compounds having —CHO groups bound to carbon atoms of rings other than six—membered aromatic rings having unsaturation outside the rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/80—Ketones containing a keto group bound to a six-membered aromatic ring containing halogen
- C07C49/813—Ketones containing a keto group bound to a six-membered aromatic ring containing halogen polycyclic
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/84—Ketones containing a keto group bound to a six-membered aromatic ring containing ether groups, groups, groups, or groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/40—Oxygen atoms
- C07D211/44—Oxygen atoms attached in position 4
- C07D211/52—Oxygen atoms attached in position 4 having an aryl radical as the second substituent in position 4
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/62—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to atoms of the carbocyclic ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/10—Spiro-condensed systems

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Neurosurgery (AREA)
Pharmacology & Pharmacy (AREA)
Biomedical Technology (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Veterinary Medicine (AREA)
Neurology (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Psychiatry (AREA)
Pain & Pain Management (AREA)
Anesthesiology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

CH1647074A 1973-12-12 1974-12-11 CH617938A5 (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US42411773A	1973-12-12	1973-12-12
US05/502,650 US3959475A (en)	1973-12-12	1974-09-03	Substituted 1,3-dihydrospiro(isobenzofuran)s

Publications (1)

Publication Number	Publication Date
CH617938A5 true CH617938A5 (fr)	1980-06-30

Family

ID=27026243

Family Applications (3)

Application Number	Title	Priority Date
CH1647074A CH617938A5 (fr)	1973-12-12	1974-12-11
CH800079A CH619228A5 (fr)	1973-12-12	1979-09-05
CH800179A CH619229A5 (fr)	1973-12-12	1979-09-05

Family Applications After (2)

Application Number	Title	Priority Date	Filing Date
CH800079A CH619228A5 (fr)	1973-12-12	1979-09-05
CH800179A CH619229A5 (fr)	1973-12-12	1979-09-05

Country Status (18)

Country	Link
US (1)	US3959475A (fr)
JP (1)	JPS5833876B2 (fr)
CA (1)	CA1051428A (fr)
CH (3)	CH617938A5 (fr)
DE (1)	DE2458177A1 (fr)
DK (1)	DK144214C (fr)
EG (1)	EG12110A (fr)
FI (1)	FI58128C (fr)
FR (1)	FR2254331B1 (fr)
GB (1)	GB1465999A (fr)
HU (1)	HU169546B (fr)
IE (1)	IE40298B1 (fr)
IL (1)	IL46201A (fr)
LU (1)	LU71461A1 (fr)
NL (1)	NL7416115A (fr)
NO (1)	NO146062C (fr)
OA (1)	OA04852A (fr)
SE (1)	SE419761B (fr)

Families Citing this family (40)

* Cited by examiner, † Cited by third party
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US4024263A (en) *	1975-04-30	1977-05-17	American Hoechst Corporation	1,3-Dihydrospiro[isobenzofuran-1,4'-piperidine]s
US3980786A (en) *	1975-07-15	1976-09-14	American Hoechst Corporation	1,3-Dihydro-3-phenyl-1'-(2-propynyl)spiro[isobenzofuran]s
US3980787A (en) *	1975-08-25	1976-09-14	American Hoechst Corporation	3-Phenylspiro[isobenzofuran-1,4'-piperidine]sulfenamides and derivatives
US3996354A (en) *	1976-01-26	1976-12-07	American Hoechst Corporation	1,3-Dihydro-1'-dimethylphosphinylalkyl-3-phenylspiro(isobenzofuran)s
US4031224A (en) *	1976-04-29	1977-06-21	American Hoechst Corporation	1,3-Dihydro-heteroarylspiro (isobenzofuran)s
US4241071A (en) *	1977-01-27	1980-12-23	American Hoechst Corporation	Antidepressant (α-phenyl-2-tolyl)azacycloalkanes
US4409229A (en) *	1977-12-02	1983-10-11	Hoechst-Roussel Pharmaceuticals, Inc.	Antidepressive and tranquilizing substituted 1,3-dihydrospiro[benzo(c)thiophene]s
EG13536A (en) *	1977-12-02	1981-12-31	Hoechst Ag	Substituted 1,3-dihydrospiro(benzo(c)thiophene)s
US4166120A (en) *	1978-04-14	1979-08-28	American Hoechst Corporation	Analgesic and tranquilizing benzoylpropyl-spiro[dihydrobenzofuran]piperidines and pyrrolidines
US4166119A (en) *	1978-04-14	1979-08-28	American Hoechst Corporation	Analgesic and tranquilizing spiro[dihydrobenzofuran]piperidines and pyrrolidines
US4301292A (en) *	1979-09-06	1981-11-17	Hoechst-Roussel Pharmaceuticals, Incorporated	1-[2-(4,5-Dihydro-4,4-dialkyl-2-oxazolyl)phenyl]-4-(dialkylamino)cyclohexanol
US4263317A (en) *	1979-09-06	1981-04-21	Hoechst-Roussel Pharmaceuticals, Inc.	Spiro[cyclohexane-1,1'(3'H)-isobenzofuran]s
US4260623A (en) *	1979-11-26	1981-04-07	Warner-Lambert Company	Hexahydro-1-arylspiro(3H-oxazolo(3,4-A)pyridine-3,4'-piperidene) antidepressants, pharmaceutical compositions thereof and method of use thereof
US4268515A (en) *	1980-02-04	1981-05-19	Hoechst-Roussel Pharmaceuticals Inc.	Spiro[dihydrobenzofuran-piperidines and-pyrrolidines], pharmaceutical compositions thereof and methods of use thereof
US4304941A (en) *	1980-08-01	1981-12-08	Hoechst Roussel Pharmaceuticals, Inc.	Method of preparing poly-substituted acylbenzenes
US4517311A (en) *	1981-10-19	1985-05-14	Hoechst-Roussel Pharmaceuticals Inc.	2'-Substituted-spiro[benzofuran-2(3H),1'-cycloalkanes] and their analgesic and anti-depressant compositions
US4404221A (en) *	1981-10-19	1983-09-13	Hoechst-Roussel Pharmaceuticals Inc.	2'-Substituted-spiro[benzofuran-2(3H),1'-cyclohexanes] and its pharmaceutical use
US4524207A (en) *	1981-10-20	1985-06-18	Hoechst-Roussel Pharmaceuticals Inc.	Process for preparing substituted 1,3-dihydrospiro[benzo(c)thiophene]s
CA1315279C (fr) *	1987-01-12	1993-03-30	Nancy Grace Bollinger	Agents antiinflammatoires
IL96507A0 (en) *	1989-12-08	1991-08-16	Merck & Co Inc	Nitrogen-containing spirocycles and pharmaceutical compositions containing them
CA2037287A1 (fr) *	1990-03-02	1991-09-03	Ben E. Evans	Antagonistes de l'oxytocine spirocyclique
EP0445974A3 (en) *	1990-03-05	1992-04-29	Merck Sharp & Dohme Ltd.	Spirocyclic antipsychotic agents
US5693643A (en) *	1991-09-16	1997-12-02	Merck & Co., Inc.	Hydantoin and succinimide-substituted derivatives of spiroindanylcamphorsulfonyl oxytocin antagonists
EP0600318B1 (fr) *	1992-11-29	1998-04-08	Clariant GmbH	Benzophénones asymétriques, halogénées et procédé de préparation
US6374762B1 (en) *	1997-10-27	2002-04-23	Correct Craft, Inc.	Water sport towing apparatus
US6433196B1 (en) *	2000-02-17	2002-08-13	Sumika Fine Chemicals Co., Ltd.	Production method of citalopram, intermediate therefor and production method of the intermediate
GB0213715D0 (en) *	2002-06-14	2002-07-24	Syngenta Ltd	Chemical compounds
US7786141B2 (en) *	2004-08-19	2010-08-31	Vertex Pharmaceuticals Incorporated	Dihydrospiroindene modulators of muscarinic receptors
KR20070046929A (ko)	2004-08-19	2007-05-03	버텍스 파마슈티칼스 인코포레이티드	무스카린 수용체 조절제
EP1817036B1 (fr) *	2004-11-29	2012-07-04	Vertex Pharmaceuticals Incorporated	Modulateurs des recepteurs muscariniques
EP1943250A1 (fr)	2005-09-09	2008-07-16	Euro-Celtique S.A.	Composes fondus et spirocycle ainsi que l'utilisation de ceux-ci
WO2007076070A2 (fr) *	2005-12-22	2007-07-05	Vertex Pharmaceuticals Incorporated	Modulateurs de recepteurs muscariniques
JP2009527568A (ja) *	2006-02-22	2009-07-30	バーテックスファーマシューティカルズインコーポレイテッド	ムスカリン受容体の調節剤
NZ570497A (en) *	2006-02-22	2011-09-30	Vertex Pharma	Spiro condensed 4,4'-quinilino-piperidines derivatives as modulators of muscarinic receptors
EP1847542A1 (fr) *	2006-04-21	2007-10-24	Laboratorios del Dr. Esteve S.A.	Dérivés de spiro[benzopyran] ou de spiro[benzofuran] comme antagonistes du récepteur sigma
JP2009542670A (ja) *	2006-06-29	2009-12-03	バーテックスファーマシューティカルズインコーポレイテッド	ムスカリン受容体の調節剤
US7696201B2 (en) *	2006-08-15	2010-04-13	Vertex Pharmaceuticals Incorporated	Modulators of muscarinic receptors
US7786107B2 (en) *	2006-08-18	2010-08-31	Vertex Pharmaceuticals Incorporated	Modulators of muscarinic receptors
US7973162B2 (en) *	2007-10-03	2011-07-05	Vertex Pharmaceuticals Incorporated	Modulators of muscarinic receptors
WO2011137024A1 (fr) *	2010-04-26	2011-11-03	Merck Sharp & Dohme Corp.	Nouveaux inhibiteurs de spiropipéridine prolylcarboxypeptidase

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* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3686186A (en) *	1970-10-05	1972-08-22	William J Houlihan	Substituted isochroman or phthalan piperidenes

1974
- 1974-09-03 US US05/502,650 patent/US3959475A/en not_active Expired - Lifetime
- 1974-12-06 IL IL7446201A patent/IL46201A/xx unknown
- 1974-12-09 DE DE19742458177 patent/DE2458177A1/de not_active Withdrawn
- 1974-12-10 FI FI3554/74A patent/FI58128C/fi active
- 1974-12-11 SE SE7415521A patent/SE419761B/xx unknown
- 1974-12-11 NL NL7416115A patent/NL7416115A/xx not_active Application Discontinuation
- 1974-12-11 DK DK644974A patent/DK144214C/da active
- 1974-12-11 CA CA215,786A patent/CA1051428A/fr not_active Expired
- 1974-12-11 EG EG546/74A patent/EG12110A/xx active
- 1974-12-11 HU HUHO1754A patent/HU169546B/hu unknown
- 1974-12-11 IE IE2648/74A patent/IE40298B1/xx unknown
- 1974-12-11 CH CH1647074A patent/CH617938A5/de not_active IP Right Cessation
- 1974-12-11 NO NO744471A patent/NO146062C/no unknown
- 1974-12-11 LU LU71461A patent/LU71461A1/xx unknown
- 1974-12-11 OA OA55362A patent/OA04852A/fr unknown
- 1974-12-12 GB GB5374474A patent/GB1465999A/en not_active Expired
- 1974-12-12 FR FR7441005A patent/FR2254331B1/fr not_active Expired
- 1974-12-12 JP JP49142997A patent/JPS5833876B2/ja not_active Expired
1979
- 1979-09-05 CH CH800079A patent/CH619228A5/de not_active IP Right Cessation
- 1979-09-05 CH CH800179A patent/CH619229A5/de not_active IP Right Cessation

Also Published As

Publication number	Publication date
DK144214C (da)	1982-06-21
CH619229A5 (fr)	1980-09-15
US3959475A (en)	1976-05-25
NO146062C (no)	1982-08-11
NL7416115A (nl)	1975-06-16
FI58128B (fi)	1980-08-29
FI58128C (fi)	1980-12-10
JPS5833876B2 (ja)	1983-07-22
FR2254331B1 (fr)	1978-07-21
GB1465999A (en)	1977-03-02
CA1051428A (fr)	1979-03-27
HU169546B (fr)	1976-12-28
SE7415521L (fr)	1975-06-13
IE40298B1 (en)	1979-04-25
LU71461A1 (fr)	1976-11-11
DK144214B (da)	1982-01-18
SE419761B (sv)	1981-08-24
FI355474A (fr)	1975-06-13
AU7624674A (en)	1976-06-10
DE2458177A1 (de)	1976-09-30
EG12110A (en)	1981-03-31
IL46201A (en)	1982-04-30
OA04852A (fr)	1980-10-31
IL46201A0 (en)	1975-03-13
NO146062B (no)	1982-04-13
CH619228A5 (fr)	1980-09-15
FR2254331A1 (fr)	1975-07-11
DK644974A (fr)	1975-08-18
JPS50100052A (fr)	1975-08-08
NO744471L (fr)	1975-07-07

Legal Events

Date	Code	Title	Description
1984-08-31	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
CH617938A5 (fr)	1980-06-30
AT365191B (de)	1981-12-28	Verfahren zur herstellung von neuen substituierten 1,3-dihydrospiro(isobenzofuranen) und ihren salzen
DE69106365T2 (de)	1995-05-04	Chinuclidinderivate.
CH648553A5 (de)	1985-03-29	Neue 3,4-dihydro-5h-2,3-benzodiazepin-derivate und verfahren zur herstellung derselben.
DE2503002A1 (de)	1975-08-14	Substituierte piperidinderivate, ein verfahren zu ihrer herstellung sowie arzneimittel
DE69120899T2 (de)	1997-02-27	Neue N-Benzoylprolin-Derivate, Verfahren zur Herstellung und diese enthaltende Arzneimittel
DE2105743A1 (en)	1972-08-31	2-(furylmethyl)-6,7-benzomorphans - useful as cns active agents
EP0004951A1 (fr)	1979-10-31	N-(3-fluorobenzoyl-propyl)-spiro-(dihydrobenzofurannepipéridines et -pyrrolidines), leurs dérivés, procédés pour leur préparation et leur utilisation pour des médicaments
DE1445845A1 (de)	1969-02-06	Neue Benzomorphane und Verfahren zu ihrer Herstellung
DE2329430A1 (de)	1974-01-03	1-acyl-3-(amino-niedrig-alkyl)-indole
EP0105210B1 (fr)	1987-03-04	Dérivés de l'isoquinoléine, leur procédé de préparation compositions pharmaceutiques les contenant et leur utilisation
DD143613A5 (de)	1980-09-03	Verfahren zur herstellung von 4-amino-2-piperidino-chinazolin-derivaten
DE2435168A1 (de)	1975-02-06	1-aryl-n-dialkylaminoalkyl-3,4dihydro-2(1h)-isochinolincarboxamide und verwandte verbindungen
DD299425A5 (de)	1992-04-16	Neue 4,4-disubstituierte piperidin-derivate und verfahren zu ihrer herstellung
DE2314639A1 (de)	1973-10-04	Pharmakodynamisch aktive aminoalkyloximaether
DE2840786C2 (fr)	1987-05-21
DE3000625A1 (de)	1980-07-17	Cis- und trans-isomere von 3-aryloxy- 4-hydroxypyrrolidinen und deren derivaten, verfahren zu ihrer herstellung und ihre verwendung
DE2748466A1 (de)	1978-05-03	4a-aryloctahydro-1h-2-pyrindine
DE2513136C3 (de)	1981-04-30	N-(1-Benzylpiperid-4-yl)-benzamide, Verfahren zu ihrer Herstellung und sie enthaltende pharmazeutische Präparate
DE1670622A1 (de)	1971-02-25	Verfahren zur Herstellung von Aminoalkyl-pyrrol-2-yl-ketonen
DE3028064C2 (fr)	1989-11-09
AT347459B (de)	1978-12-27	Verfahren zur herstellung von neuen substi- tuierten 1,3-dihydrospiro(isobenzofuranen) sowie von optischen antipoden und saeure- additionssalzen dieser verbindungen
EP0123998A2 (fr)	1984-11-07	4-Phényl-tétrahydro-furano-pyridines, procédé pour leur préparation et composés pharmaceutiques
CH556837A (de)	1974-12-13	Verfahren zur herstellung neuer spiroindanpyrrolidinderivate.
DE69007904T2 (de)	1994-07-21	1-Oxa-2-oxo-8-azaspiro[4,5]decan-Derivate, Verfahren zu ihrer Herstellung und pharmazeutische Zusammensetzungen daraus.