CH501005A - Verfahren zur Herstellung von tricyclischen Verbindungen - Google Patents

Verfahren zur Herstellung von tricyclischen Verbindungen

Info

Publication number: CH501005A
Authority: CH; Switzerland
Prior art keywords: ether; amino; compound; halogen; chloro
Prior art date: 1961-02-08

Application number

CH380261A

Other languages

German (de)

English (en)

Inventor

Gerald Dr Rey-Bellet

Hans Dr Spiegelberg

Original Assignee

Hoffmann La Roche

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.)

1961-02-08

Filing date

1961-03-30

Publication date

1970-12-31

1961-02-08 Priority claimed from CH146761A external-priority patent/CH419104A/de

1961-03-30 Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche

1961-03-30 Priority to CH380261A priority Critical patent/CH501005A/de

1962-01-16 Priority to DE19621793621 priority patent/DE1793621A1/de

1962-01-16 Priority to DE1443983A priority patent/DE1443983C3/de

1962-02-01 Priority to BE613363A priority patent/BE613363A/fr

1962-02-05 Priority to GB4304/62A priority patent/GB957230A/en

1962-02-06 Priority to FI0242/62A priority patent/FI41390B/fi

1962-02-07 Priority to SE6916906*3A priority patent/SE384024B/xx

1962-02-07 Priority to DK58662AA priority patent/DK104299C/da

1962-02-07 Priority to SE1324/62A priority patent/SE317666B/xx

1962-02-07 Priority to ES0274394A priority patent/ES274394A1/es

1963-02-05 Priority to GB42825/63A priority patent/GB986875A/en

1964-12-26 Priority to OA51047A priority patent/OA00952A/fr

1967-04-12 Priority to SE05107/67A priority patent/SE336348B/xx

1969-01-21 Priority to SE00780/69A priority patent/SE350483B/xx

1969-01-21 Priority to SE00781/69A priority patent/SE350481B/xx

1969-04-23 Priority to FI691201A priority patent/FI46062C/fi

1970-12-31 Publication of CH501005A publication Critical patent/CH501005A/de

Links

-1 aralkoxy Chemical group 0.000 claims abstract description 36
125000003118 aryl group Chemical group 0.000 claims abstract description 19
125000001033 ether group Chemical group 0.000 claims abstract description 18
125000003545 alkoxy group Chemical group 0.000 claims abstract description 13
229910052736 halogen Inorganic materials 0.000 claims abstract description 12
150000002367 halogens Chemical class 0.000 claims abstract description 12
125000002252 acyl group Chemical group 0.000 claims abstract description 11
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 11
125000000217 alkyl group Chemical group 0.000 claims abstract description 9
125000004414 alkyl thio group Chemical group 0.000 claims abstract description 9
125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 9
125000004659 aryl alkyl thio group Chemical group 0.000 claims abstract description 9
125000004104 aryloxy group Chemical group 0.000 claims abstract description 9
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 9
125000005110 aryl thio group Chemical group 0.000 claims abstract description 8
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims abstract description 8
239000000047 product Substances 0.000 claims abstract description 8
239000007795 chemical reaction product Substances 0.000 claims abstract description 6
125000006239 protecting group Chemical group 0.000 claims abstract description 6
125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims abstract description 6
230000010933 acylation Effects 0.000 claims abstract description 5
238000005917 acylation reaction Methods 0.000 claims abstract description 5
238000005907 ketalization reaction Methods 0.000 claims abstract description 5
125000001931 aliphatic group Chemical group 0.000 claims abstract description 4
230000032050 esterification Effects 0.000 claims abstract description 4
238000005886 esterification reaction Methods 0.000 claims abstract description 4
125000001302 tertiary amino group Chemical group 0.000 claims abstract description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 62
238000000034 method Methods 0.000 claims description 27
150000001875 compounds Chemical class 0.000 claims description 22
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 21
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 20
238000006243 chemical reaction Methods 0.000 claims description 17
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 14
125000003277 amino group Chemical class 0.000 claims description 12
238000009835 boiling Methods 0.000 claims description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
150000002366 halogen compounds Chemical class 0.000 claims description 11
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 10
150000001412 amines Chemical class 0.000 claims description 10
230000018044 dehydration Effects 0.000 claims description 10
238000006297 dehydration reaction Methods 0.000 claims description 10
239000000203 mixture Substances 0.000 claims description 10
150000003839 salts Chemical group 0.000 claims description 10
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 9
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 9
125000004432 carbon atom Chemical group C* 0.000 claims description 8
238000001816 cooling Methods 0.000 claims description 8
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
238000002360 preparation method Methods 0.000 claims description 8
239000011541 reaction mixture Substances 0.000 claims description 8
229910000042 hydrogen bromide Inorganic materials 0.000 claims description 7
229910052938 sodium sulfate Inorganic materials 0.000 claims description 7
235000011152 sodium sulphate Nutrition 0.000 claims description 7
NZJXNTXQQCDVBM-UHFFFAOYSA-N 9-(3-bromopropylidene)-2-chlorothioxanthene Chemical compound ClC1=CC=2C(C3=CC=CC=C3SC2C=C1)=CCCBr NZJXNTXQQCDVBM-UHFFFAOYSA-N 0.000 claims description 6
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 6
238000004821 distillation Methods 0.000 claims description 6
150000002902 organometallic compounds Chemical class 0.000 claims description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 6
239000013078 crystal Substances 0.000 claims description 5
239000000155 melt Substances 0.000 claims description 5
150000002736 metal compounds Chemical class 0.000 claims description 5
150000003141 primary amines Chemical class 0.000 claims description 5
150000003335 secondary amines Chemical class 0.000 claims description 5
239000007787 solid Substances 0.000 claims description 5
239000002253 acid Substances 0.000 claims description 4
239000008346 aqueous phase Substances 0.000 claims description 4
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
229910052794 bromium Inorganic materials 0.000 claims description 4
238000002844 melting Methods 0.000 claims description 4
230000008018 melting Effects 0.000 claims description 4
230000007935 neutral effect Effects 0.000 claims description 4
239000003208 petroleum Substances 0.000 claims description 4
HTGCVLNFLVVCST-UHFFFAOYSA-N 1-piperazin-1-ylethanol Chemical compound CC(O)N1CCNCC1 HTGCVLNFLVVCST-UHFFFAOYSA-N 0.000 claims description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
239000003795 chemical substances by application Substances 0.000 claims description 3
230000001419 dependent effect Effects 0.000 claims description 3
229910000027 potassium carbonate Inorganic materials 0.000 claims description 3
238000010992 reflux Methods 0.000 claims description 3
229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 3
235000017557 sodium bicarbonate Nutrition 0.000 claims description 3
DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 claims description 2
ZCDADJXRUCOCJE-UHFFFAOYSA-N 2-chlorothioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(Cl)=CC=C3SC2=C1 ZCDADJXRUCOCJE-UHFFFAOYSA-N 0.000 claims description 2
ZVQOOHYFBIDMTQ-UHFFFAOYSA-N [methyl(oxido){1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-lambda(6)-sulfanylidene]cyanamide Chemical compound N#CN=S(C)(=O)C(C)C1=CC=C(C(F)(F)F)N=C1 ZVQOOHYFBIDMTQ-UHFFFAOYSA-N 0.000 claims description 2
WSPOMRSOLSGNFJ-UHFFFAOYSA-N chlorprothixene Chemical compound C1=C(Cl)C=C2C(=CCCN(C)C)C3=CC=CC=C3SC2=C1 WSPOMRSOLSGNFJ-UHFFFAOYSA-N 0.000 claims description 2
125000005265 dialkylamine group Chemical group 0.000 claims description 2
238000001035 drying Methods 0.000 claims description 2
MDKXBBPLEGPIRI-UHFFFAOYSA-N ethoxyethane;methanol Chemical compound OC.CCOCC MDKXBBPLEGPIRI-UHFFFAOYSA-N 0.000 claims description 2
239000012442 inert solvent Substances 0.000 claims description 2
238000011081 inoculation Methods 0.000 claims description 2
GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 claims description 2
150000002894 organic compounds Chemical class 0.000 claims description 2
239000002904 solvent Substances 0.000 claims description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
239000000460 chlorine Substances 0.000 claims 1
229910052801 chlorine Inorganic materials 0.000 claims 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract description 3
208000010513 Stupor Diseases 0.000 abstract description 2
230000002908 adrenolytic effect Effects 0.000 abstract description 2
230000003474 anti-emetic effect Effects 0.000 abstract description 2
230000001754 anti-pyretic effect Effects 0.000 abstract description 2
239000002111 antiemetic agent Substances 0.000 abstract description 2
239000002221 antipyretic Substances 0.000 abstract description 2
230000003301 hydrolyzing effect Effects 0.000 abstract description 2
230000002631 hypothermal effect Effects 0.000 abstract description 2
239000000932 sedative agent Substances 0.000 abstract description 2
230000001624 sedative effect Effects 0.000 abstract description 2
YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 abstract description 2
229910019213 POCl3 Inorganic materials 0.000 abstract 1
GUGOEEXESWIERI-UHFFFAOYSA-N Terfenadine Chemical compound C1=CC(C(C)(C)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 GUGOEEXESWIERI-UHFFFAOYSA-N 0.000 abstract 1
125000001118 alkylidene group Chemical group 0.000 abstract 1
230000003444 anaesthetic effect Effects 0.000 abstract 1
230000001387 anti-histamine Effects 0.000 abstract 1
239000000739 antihistaminic agent Substances 0.000 abstract 1
125000004356 hydroxy functional group Chemical group O* 0.000 abstract 1
239000000243 solution Substances 0.000 description 10
UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 8
230000007062 hydrolysis Effects 0.000 description 5
238000006460 hydrolysis reaction Methods 0.000 description 5
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 4
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
150000001350 alkyl halides Chemical class 0.000 description 4
239000005457 ice water Substances 0.000 description 4
239000011777 magnesium Substances 0.000 description 4
229910052749 magnesium Inorganic materials 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
239000011230 binding agent Substances 0.000 description 3
230000015572 biosynthetic process Effects 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
238000000354 decomposition reaction Methods 0.000 description 3
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 3
150000007522 mineralic acids Chemical class 0.000 description 3
150000007524 organic acids Chemical class 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
BQLHMMQUVJCTAN-UHFFFAOYSA-N 1-chloro-3-methoxypropane Chemical compound COCCCCl BQLHMMQUVJCTAN-UHFFFAOYSA-N 0.000 description 2
HUSKVODZFFQATD-UHFFFAOYSA-N 2-chloro-9-(3-methoxypropyl)thioxanthen-9-ol Chemical compound ClC1=CC=2C(C3=CC=CC=C3SC=2C=C1)(CCCOC)O HUSKVODZFFQATD-UHFFFAOYSA-N 0.000 description 2
WIZXNWBAMBCJAU-UHFFFAOYSA-N 9-(3-bromopropylidene)thioxanthene Chemical compound C1=CC=C2C(=CCCBr)C3=CC=CC=C3SC2=C1 WIZXNWBAMBCJAU-UHFFFAOYSA-N 0.000 description 2
FZKDHMKGZGXIQV-UHFFFAOYSA-N 9-(3-methoxypropyl)thioxanthen-9-ol Chemical compound OC1(C2=CC=CC=C2SC=2C=CC=CC1=2)CCCOC FZKDHMKGZGXIQV-UHFFFAOYSA-N 0.000 description 2
KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 2
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
150000002681 magnesium compounds Chemical class 0.000 description 2
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 2
239000012044 organic layer Substances 0.000 description 2
239000000825 pharmaceutical preparation Substances 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
239000007858 starting material Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
239000000126 substance Substances 0.000 description 2
239000000725 suspension Substances 0.000 description 2
JMVMXFREZLYKAO-UHFFFAOYSA-N 1-(3-thioxanthen-9-ylidenepropyl)piperidine Chemical compound N1(CCCCC1)CCC=C1C2=CC=CC=C2SC=2C=CC=CC1=2 JMVMXFREZLYKAO-UHFFFAOYSA-N 0.000 description 1
CAPCBAYULRXQAN-UHFFFAOYSA-N 1-n,1-n-diethylpentane-1,4-diamine Chemical compound CCN(CC)CCCC(C)N CAPCBAYULRXQAN-UHFFFAOYSA-N 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
PQJUJGAVDBINPI-UHFFFAOYSA-N 9H-thioxanthene Chemical group C1=CC=C2CC3=CC=CC=C3SC2=C1 PQJUJGAVDBINPI-UHFFFAOYSA-N 0.000 description 1
RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-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
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
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 1
235000011054 acetic acid Nutrition 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
125000004183 alkoxy alkyl group Chemical group 0.000 description 1
235000019270 ammonium chloride Nutrition 0.000 description 1
150000001555 benzenes Chemical class 0.000 description 1
AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 1
RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
239000000872 buffer Substances 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
239000012876 carrier material Substances 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
235000015165 citric acid Nutrition 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
150000008050 dialkyl sulfates Chemical class 0.000 description 1
ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
239000003814 drug Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
238000001640 fractional crystallisation Methods 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
150000003840 hydrochlorides Chemical group 0.000 description 1
HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000004310 lactic acid Substances 0.000 description 1
235000014655 lactic acid Nutrition 0.000 description 1
239000007788 liquid Substances 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
239000003589 local anesthetic agent Substances 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
239000000463 material Substances 0.000 description 1
229940102396 methyl bromide Drugs 0.000 description 1
JJSMYTSEKDSFKK-UHFFFAOYSA-N n,n-dimethyl-3-thioxanthen-9-ylidenepropan-1-amine Chemical compound C1=CC=C2C(=CCCN(C)C)C3=CC=CC=C3SC2=C1 JJSMYTSEKDSFKK-UHFFFAOYSA-N 0.000 description 1
KKTBUCVHSCATGB-UHFFFAOYSA-N n-methylcyclopentanamine Chemical compound CNC1CCCC1 KKTBUCVHSCATGB-UHFFFAOYSA-N 0.000 description 1
210000000653 nervous system Anatomy 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
125000002524 organometallic group Chemical group 0.000 description 1
230000003204 osmotic effect Effects 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
HDOWRFHMPULYOA-UHFFFAOYSA-N piperidin-4-ol Chemical compound OC1CCNCC1 HDOWRFHMPULYOA-UHFFFAOYSA-N 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 1
NBOMNTLFRHMDEZ-UHFFFAOYSA-N thiosalicylic acid Chemical class OC(=O)C1=CC=CC=C1S NBOMNTLFRHMDEZ-UHFFFAOYSA-N 0.000 description 1
229940103494 thiosalicylic acid Drugs 0.000 description 1
150000005075 thioxanthenes Chemical class 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Classifications

- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03D—APPARATUS FOR PROCESSING EXPOSED PHOTOGRAPHIC MATERIALS; ACCESSORIES THEREFOR
- G03D15/00—Apparatus for treating processed material
- G03D15/02—Drying; Glazing
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/02—Halogenated hydrocarbons
- A61K31/025—Halogenated hydrocarbons carbocyclic
- A61K31/03—Halogenated hydrocarbons carbocyclic aromatic
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/12—Ketones
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/13—Amines
- A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C23/00—Compounds containing at least one halogen atom bound to a ring other than a six-membered aromatic ring
- C07C23/18—Polycyclic halogenated hydrocarbons
- C07C23/20—Polycyclic halogenated hydrocarbons with condensed rings none of which is aromatic
- C07C23/38—Polycyclic halogenated hydrocarbons with condensed rings none of which is aromatic with three condensed rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
- C07C41/30—Preparation of ethers by reactions not forming ether-oxygen bonds by increasing the number of carbon atoms, e.g. by oligomerisation
- 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
- C07C43/178—Unsaturated ethers containing hydroxy or O-metal groups
- C07C43/1788—Unsaturated ethers containing hydroxy or O-metal groups containing six-membered aromatic rings and other rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/10—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D335/00—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom
- C07D335/04—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D335/10—Dibenzothiopyrans; Hydrogenated dibenzothiopyrans
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D335/00—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom
- C07D335/04—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D335/10—Dibenzothiopyrans; Hydrogenated dibenzothiopyrans
- C07D335/12—Thioxanthenes
- C07D335/20—Thioxanthenes with hydrocarbon radicals, substituted by amino radicals, directly attached in position 9
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01G—CAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES, LIGHT-SENSITIVE OR TEMPERATURE-SENSITIVE DEVICES OF THE ELECTROLYTIC TYPE
- H01G4/00—Fixed capacitors; Processes of their manufacture
- H01G4/38—Multiple capacitors, i.e. structural combinations of fixed capacitors
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/30—Ortho- or ortho- and peri-condensed systems containing three rings containing seven-membered rings
- C07C2603/32—Dibenzocycloheptenes; Hydrogenated dibenzocycloheptenes
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Engineering & Computer Science (AREA)
Epidemiology (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Medicinal Chemistry (AREA)
Power Engineering (AREA)
Pharmacology & Pharmacy (AREA)
Physics & Mathematics (AREA)
General Physics & Mathematics (AREA)
Chemical Kinetics & Catalysis (AREA)
Manufacturing & Machinery (AREA)
Microelectronics & Electronic Packaging (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

CH380261A 1961-02-08 1961-03-30 Verfahren zur Herstellung von tricyclischen Verbindungen CH501005A (de)

Priority Applications (16)

Application Number	Priority Date	Filing Date	Title
CH380261A CH501005A (de)	1961-02-08	1961-03-30	Verfahren zur Herstellung von tricyclischen Verbindungen
DE19621793621 DE1793621A1 (de)	1961-02-08	1962-01-16	Tricyclische Verbindungen
DE1443983A DE1443983C3 (de)	1961-02-08	1962-01-16	Verfahren zur Herstellung von Aminoalkylidenverbindungen des Dibenzo eckige Klammer auf a,d eckige Klammer zu -cycloheptene bzw. des Thioxanthens aus den zugehörigen 5- bzw. 9-Ketoverbindungen
BE613363A BE613363A (fr)	1961-02-08	1962-02-01	Procédé pour la préparation de composés tricycliques
GB4304/62A GB957230A (en)	1961-02-08	1962-02-05	Tricyclic compounds and their manufacture
FI0242/62A FI41390B (fr)	1961-02-08	1962-02-06
ES0274394A ES274394A1 (es)	1961-02-08	1962-02-07	Procedimiento para la fabricación de aminas secundarias tricíclicas
SE6916906*3A SE384024B (sv)	1961-03-30	1962-02-07	9-hydroxi-9-(3'-alkoxi-propyl)-tioxanten-derivat for framstellning av farmakologiskt aktiva tiaxantenforeningar
DK58662AA DK104299C (da)	1961-02-08	1962-02-07	Fremgangsmåde til fremstilling af tertiæraminoalkylidensubstituerede dibenzocycloheptadien-, dibenzocycloheptatrien- eller thioxanthenforbindelser eller syreadditionssalte eller kvaternære ammoniumforbindelser deraf.
SE1324/62A SE317666B (fr)	1961-02-08	1962-02-07
GB42825/63A GB986875A (en)	1961-02-08	1963-02-05	The manufacture of halogeno-alkylidene tricyclic compounds and the conversion thereof
OA51047A OA00952A (fr)	1961-02-08	1964-12-26	Procédé pour la préparation de composés tricycliques.
SE05107/67A SE336348B (fr)	1961-03-30	1967-04-12
SE00780/69A SE350483B (fr)	1961-02-08	1969-01-21
SE00781/69A SE350481B (fr)	1961-02-08	1969-01-21
FI691201A FI46062C (fi)	1961-02-08	1969-04-23	Trisyklisesti substituoitu alkyylieetteri, joka on välituote terapeutt isesti vaikuttavien 5-amino-alkylideeni-dibentso/a,e/syklohepta-/1,5/d ieenien-,-dibentso/a,e/syklohepta/1,3,5/trieenien ja 9-amino-alkylidee ni-tioksanteenien valmistuksessa.

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
CH146761A CH419104A (de)	1961-02-08	1961-02-08	Verfahren zur Herstellung von tricyclischen Verbindungen
CH380261A CH501005A (de)	1961-02-08	1961-03-30	Verfahren zur Herstellung von tricyclischen Verbindungen

Publications (1)

Publication Number	Publication Date
CH501005A true CH501005A (de)	1970-12-31

Family

ID=25687732

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH380261A CH501005A (de)	1961-02-08	1961-03-30	Verfahren zur Herstellung von tricyclischen Verbindungen

Country Status (8)

Country	Link
BE (1)	BE613363A (fr)
CH (1)	CH501005A (fr)
DE (2)	DE1793621A1 (fr)
DK (1)	DK104299C (fr)
FI (2)	FI41390B (fr)
GB (2)	GB957230A (fr)
OA (1)	OA00952A (fr)
SE (3)	SE317666B (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3258399A (en) *	1962-09-13	1966-06-28	Colgate Palmolive Co	Method of inducing central nervous system stimulation
US3359161A (en) *	1963-08-29	1967-12-19	Kefalas As	Thiaxanthenols, process of producing and anti-tussive compositions thereof

1961
- 1961-03-30 CH CH380261A patent/CH501005A/de not_active IP Right Cessation
1962
- 1962-01-16 DE DE19621793621 patent/DE1793621A1/de active Pending
- 1962-01-16 DE DE1443983A patent/DE1443983C3/de not_active Expired
- 1962-02-01 BE BE613363A patent/BE613363A/fr unknown
- 1962-02-05 GB GB4304/62A patent/GB957230A/en not_active Expired
- 1962-02-06 FI FI0242/62A patent/FI41390B/fi active
- 1962-02-07 DK DK58662AA patent/DK104299C/da active
- 1962-02-07 SE SE1324/62A patent/SE317666B/xx unknown
1963
- 1963-02-05 GB GB42825/63A patent/GB986875A/en not_active Expired
1964
- 1964-12-26 OA OA51047A patent/OA00952A/fr unknown
1969
- 1969-01-21 SE SE00781/69A patent/SE350481B/xx unknown
- 1969-01-21 SE SE00780/69A patent/SE350483B/xx unknown
- 1969-04-23 FI FI691201A patent/FI46062C/fi active

Also Published As

Publication number	Publication date
OA00952A (fr)	1968-03-22
SE317666B (fr)	1969-11-24
GB957230A (en)	1964-05-06
DE1443983C3 (de)	1975-07-10
BE613363A (fr)	1962-08-01
DE1443983B2 (de)	1974-11-28
DE1793621A1 (de)	1971-11-18
GB986875A (en)	1965-03-24
FI46062B (fr)	1972-08-31
SE350483B (fr)	1972-10-30
FI46062C (fi)	1972-12-11
FI41390B (fr)	1969-07-31
SE350481B (fr)	1972-10-30
DK104299C (da)	1966-05-02
DE1443983A1 (de)	1969-01-16

Legal Events

Date	Code	Title	Description
1981-04-30	PL	Patent ceased

Publication	Publication Date	Title
DE68924529T2 (de)	1996-05-15	Thiochromanester von Phenolen und Terephthalaten mit retinoidähnlicher Wirkung.
DE2809377A1 (de)	1979-09-13	Phenoxyalkylcarbonsaeure-derivate, verfahren zu deren herstellung sowie diese verbindungen enthaltende arzneimittel
DE2803651C2 (fr)	1988-10-20
CH501005A (de)	1970-12-31	Verfahren zur Herstellung von tricyclischen Verbindungen
DE68902946T2 (de)	1993-04-29	Heteroarotinoid-derivate, verfahren zu deren herstellung und diese enthaltende pharmazeutische zusammenstellungen.
AT240866B (de)	1965-06-25	Verfahren zur Herstellung von basisch substituierten Dibenzoderivaten
US3432549A (en)	1969-03-11	Pharmacologically active new substituted benzamides
EP0003105B1 (fr)	1981-05-20	Procédé d'anilidation d'esters d'acide carboxylique
DE3306996A1 (de)	1984-08-30	Acrylsaeuremorpholide, ihre herstellung und verwendung
AT237589B (de)	1964-12-28	Verfahren zur Herstellung von basisch substituierten Dibenzoderivaten und deren Säureadditionssalzen oder quaternären Verbindungen
CH419104A (de)	1966-08-31	Verfahren zur Herstellung von tricyclischen Verbindungen
AT228775B (de)	1963-08-12	Verfahren zur Herstellung von 5-(γ-Sekundäraminopropyliden)-dibenzoheptaenverbindungen und deren Salzen
DE893950C (de)	1953-10-22	Verfahren zur Herstellung von 2-Halogen-4-aminoalkylaminotoluolen
CH356759A (de)	1961-09-15	Verfahren zur Herstellung von Dibenzo-cycloheptaenen
DE1668233A1 (de)	1969-08-21	Verfahren zur Herstellung von tricyclischen sekundaeren Aminen
AT330181B (de)	1976-06-25	Verfahren zur herstellung von neuen chinolinessigsaurederivaten und ihren salzen
AT220609B (de)	1962-04-10	Verfahren zur Herstellung von neuen Dibenzo-cycloheptaen-Verbindungen und deren salzartigen Abkömmlingen
AT233014B (de)	1964-04-25	Verfahren zur Herstellung von neuen Iminodibenzylderivaten
AT332864B (de)	1976-10-25	Verfahren zur herstellung von neuen diphenylmethoxyathylaminen und deren additionssalzen
DE1445800C (de)	1971-04-15	Verfahren zur Herstellung von Diben zoazepinen
DE2511621A1 (de)	1976-02-26	Verfahren zur herstellung neuer heterocyclischer verbindungen
AT235293B (de)	1964-08-25	Verfahren zur Herstellung von neuen Piperidinderivaten
AT248441B (de)	1966-07-25	Verfahren zur Herstellung von neuen Salicylsäurederivaten
AT218509B (de)	1961-12-11	Verfahren zur Herstellung von basisch substituierten Carbinolen, sowie von ihren sterisch einheitlichen Razematen und deren optisch aktiven Komponenten und/oder ihren Säureadditionssalzen
AT330779B (de)	1976-07-26	Verfahren zur herstellung von neuen chinolinessigsaurederivaten und ihren salzen