NO131594B - - Google Patents

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Info

Publication number: NO131594B
Authority: NO; Norway
Prior art keywords: residue; propenyl; acid; dihydro; formula
Prior art date: 1971-02-23

Application number

NO538/72A

Other languages

English (en)

Norwegian (no)

Other versions

NO131594C (da

Inventor

D Beck

R Bernasconi

K Schenker

A Storni

M Wilhelm

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.)

1971-02-23

Filing date

1972-02-22

Publication date

1975-03-17

1971-02-23 Priority claimed from CH257771A external-priority patent/CH552558A/de

1972-01-17 Priority claimed from CH68872A external-priority patent/CH612805A5/xx

1972-02-22 Application filed by Ciba Geigy Ag filed Critical Ciba Geigy Ag

1975-03-17 Publication of NO131594B publication Critical patent/NO131594B/no

1975-06-25 Publication of NO131594C publication Critical patent/NO131594C/no

Links

150000001875 compounds Chemical class 0.000 claims description 35
239000002253 acid Substances 0.000 claims description 22
150000003839 salts Chemical class 0.000 claims description 20
238000000034 method Methods 0.000 claims description 14
150000002148 esters Chemical class 0.000 claims description 10
125000004432 carbon atom Chemical group C* 0.000 claims description 8
229910052757 nitrogen Inorganic materials 0.000 claims description 8
125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
125000004043 oxo group Chemical group O=* 0.000 claims description 8
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
125000000217 alkyl group Chemical group 0.000 claims description 5
125000003277 amino group Chemical group 0.000 claims description 5
125000001424 substituent group Chemical group 0.000 claims description 5
150000003512 tertiary amines Chemical class 0.000 claims description 5
125000003282 alkyl amino group Chemical group 0.000 claims description 4
239000007795 chemical reaction product Substances 0.000 claims description 4
230000003287 optical effect Effects 0.000 claims description 4
238000002360 preparation method Methods 0.000 claims description 4
230000000506 psychotropic effect Effects 0.000 claims description 4
150000003335 secondary amines Chemical class 0.000 claims description 4
125000006310 cycloalkyl amino group Chemical group 0.000 claims description 2
230000007062 hydrolysis Effects 0.000 claims description 2
238000006460 hydrolysis reaction Methods 0.000 claims description 2
230000008569 process Effects 0.000 claims description 2
230000001225 therapeutic effect Effects 0.000 claims 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 41
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 38
239000000243 solution Substances 0.000 description 38
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 36
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 26
-1 methylamino, ethylamino, propylamino, isopropylamino Chemical group 0.000 description 26
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 23
238000002844 melting Methods 0.000 description 23
230000008018 melting Effects 0.000 description 23
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 22
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 17
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 17
238000006243 chemical reaction Methods 0.000 description 17
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 17
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 14
239000002585 base Substances 0.000 description 13
229910052938 sodium sulfate Inorganic materials 0.000 description 13
235000011152 sodium sulphate Nutrition 0.000 description 13
239000007858 starting material Substances 0.000 description 13
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 12
239000013078 crystal Substances 0.000 description 12
238000003756 stirring Methods 0.000 description 12
239000000203 mixture Substances 0.000 description 11
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 10
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 10
239000011541 reaction mixture Substances 0.000 description 10
150000007513 acids Chemical class 0.000 description 9
239000003795 chemical substances by application Substances 0.000 description 9
239000000155 melt Substances 0.000 description 9
239000012279 sodium borohydride Substances 0.000 description 9
229910000033 sodium borohydride Inorganic materials 0.000 description 9
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 8
238000001953 recrystallisation Methods 0.000 description 8
235000011121 sodium hydroxide Nutrition 0.000 description 8
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 7
229940098779 methanesulfonic acid Drugs 0.000 description 7
230000009467 reduction Effects 0.000 description 7
238000006722 reduction reaction Methods 0.000 description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
230000002378 acidificating effect Effects 0.000 description 6
238000001816 cooling Methods 0.000 description 6
239000003921 oil Substances 0.000 description 6
235000019198 oils Nutrition 0.000 description 6
239000002904 solvent Substances 0.000 description 6
239000000126 substance Substances 0.000 description 6
NLHDGEXLFCDTHQ-BJMVGYQFSA-N (e)-3-anthracen-9-ylprop-2-enal Chemical class C1=CC=C2C(/C=C/C=O)=C(C=CC=C3)C3=CC2=C1 NLHDGEXLFCDTHQ-BJMVGYQFSA-N 0.000 description 5
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
229960000583 acetic acid Drugs 0.000 description 5
230000000694 effects Effects 0.000 description 5
239000000706 filtrate Substances 0.000 description 5
235000019253 formic acid Nutrition 0.000 description 5
229940013688 formic acid Drugs 0.000 description 5
238000010438 heat treatment Methods 0.000 description 5
238000007912 intraperitoneal administration Methods 0.000 description 5
238000010992 reflux Methods 0.000 description 5
239000000725 suspension Substances 0.000 description 5
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
235000011054 acetic acid Nutrition 0.000 description 4
150000008044 alkali metal hydroxides Chemical class 0.000 description 4
239000008346 aqueous phase Substances 0.000 description 4
UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 4
238000009833 condensation Methods 0.000 description 4
230000005494 condensation Effects 0.000 description 4
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 4
ZKQFHRVKCYFVCN-UHFFFAOYSA-N ethoxyethane;hexane Chemical compound CCOCC.CCCCCC ZKQFHRVKCYFVCN-UHFFFAOYSA-N 0.000 description 4
XEKOWRVHYACXOJ-UHFFFAOYSA-N ethyl acetate Substances CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 4
239000001257 hydrogen Substances 0.000 description 4
229910052739 hydrogen Inorganic materials 0.000 description 4
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
229910000041 hydrogen chloride Inorganic materials 0.000 description 4
239000005457 ice water Substances 0.000 description 4
229910052744 lithium Inorganic materials 0.000 description 4
150000007522 mineralic acids Chemical class 0.000 description 4
150000007524 organic acids Chemical class 0.000 description 4
239000012074 organic phase Substances 0.000 description 4
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
239000000047 product Substances 0.000 description 4
125000006017 1-propenyl group Chemical group 0.000 description 3
QQFOYBYVRWBGGB-UHFFFAOYSA-N 3-anthracen-9-yl-N-methylprop-2-en-1-amine Chemical compound CNCC=CC=1C2=CC=CC=C2C=C2C=CC=CC12 QQFOYBYVRWBGGB-UHFFFAOYSA-N 0.000 description 3
RVLPMOASZWJYHU-UHFFFAOYSA-N 3-anthracen-9-yl-N-methylprop-2-en-1-imine Chemical compound CN=CC=CC=1C2=CC=CC=C2C=C2C=CC=CC12 RVLPMOASZWJYHU-UHFFFAOYSA-N 0.000 description 3
FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 3
239000005977 Ethylene Substances 0.000 description 3
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
241001465754 Metazoa Species 0.000 description 3
241000700159 Rattus Species 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
150000001299 aldehydes Chemical class 0.000 description 3
229910001854 alkali hydroxide Inorganic materials 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
239000003054 catalyst Substances 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
238000000605 extraction Methods 0.000 description 3
150000004678 hydrides Chemical class 0.000 description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 3
238000004519 manufacturing process Methods 0.000 description 3
229910052987 metal hydride Inorganic materials 0.000 description 3
150000004681 metal hydrides Chemical class 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
230000007935 neutral effect Effects 0.000 description 3
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 3
239000000825 pharmaceutical preparation Substances 0.000 description 3
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 3
238000000746 purification Methods 0.000 description 3
235000017557 sodium bicarbonate Nutrition 0.000 description 3
229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
239000011701 zinc Substances 0.000 description 3
229910052725 zinc Inorganic materials 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
PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 2
LULAYUGMBFYYEX-UHFFFAOYSA-N 3-chlorobenzoic acid Chemical compound OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 2
HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 2
ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 2
BLUNNZYDUZHPAD-UHFFFAOYSA-N 4-methylbenzenesulfonic acid;dihydrate Chemical compound O.O.CC1=CC=C(S(O)(=O)=O)C=C1 BLUNNZYDUZHPAD-UHFFFAOYSA-N 0.000 description 2
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
206010013710 Drug interaction Diseases 0.000 description 2
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
239000005909 Kieselgur Substances 0.000 description 2
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-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
LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-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
238000010521 absorption reaction Methods 0.000 description 2
125000002252 acyl group Chemical group 0.000 description 2
239000003513 alkali Substances 0.000 description 2
BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 2
YMNKUHIVVMFOFO-UHFFFAOYSA-N anthracene-9-carbaldehyde Chemical compound C1=CC=C2C(C=O)=C(C=CC=C3)C3=CC2=C1 YMNKUHIVVMFOFO-UHFFFAOYSA-N 0.000 description 2
RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
238000009835 boiling Methods 0.000 description 2
229910000085 borane Inorganic materials 0.000 description 2
125000001589 carboacyl group Chemical group 0.000 description 2
239000003610 charcoal Substances 0.000 description 2
239000003638 chemical reducing agent Substances 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
238000003776 cleavage reaction Methods 0.000 description 2
239000012230 colorless oil Substances 0.000 description 2
125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 2
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 2
USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
239000003480 eluent Substances 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
239000000284 extract Substances 0.000 description 2
KWIUHFFTVRNATP-UHFFFAOYSA-N glycine betaine Chemical compound C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 2
125000005597 hydrazone group Chemical group 0.000 description 2
150000007857 hydrazones Chemical class 0.000 description 2
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical class I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
230000003301 hydrolyzing effect Effects 0.000 description 2
229910052500 inorganic mineral Inorganic materials 0.000 description 2
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
239000007788 liquid Substances 0.000 description 2
239000012280 lithium aluminium hydride Substances 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
239000001630 malic acid Substances 0.000 description 2
235000011090 malic acid Nutrition 0.000 description 2
229940099690 malic acid Drugs 0.000 description 2
230000011987 methylation Effects 0.000 description 2
238000007069 methylation reaction Methods 0.000 description 2
235000010755 mineral Nutrition 0.000 description 2
239000011707 mineral Substances 0.000 description 2
239000012299 nitrogen atmosphere Substances 0.000 description 2
GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
239000012071 phase Substances 0.000 description 2
229910052697 platinum Inorganic materials 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
125000004368 propenyl group Chemical group C(=CC)* 0.000 description 2
235000019260 propionic acid Nutrition 0.000 description 2
229940095574 propionic acid Drugs 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 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
150000003254 radicals Chemical class 0.000 description 2
YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
230000007017 scission Effects 0.000 description 2
150000007659 semicarbazones Chemical group 0.000 description 2
QMGVPVSNSZLJIA-FVWCLLPLSA-N strychnine Chemical compound O([C@H]1CC(N([C@H]2[C@H]1[C@H]1C3)C=4C5=CC=CC=4)=O)CC=C1CN1[C@@H]3[C@]25CC1 QMGVPVSNSZLJIA-FVWCLLPLSA-N 0.000 description 2
239000011975 tartaric acid Substances 0.000 description 2
235000002906 tartaric acid Nutrition 0.000 description 2
229960001367 tartaric acid Drugs 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
DNXIKVLOVZVMQF-UHFFFAOYSA-N (3beta,16beta,17alpha,18beta,20alpha)-17-hydroxy-11-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-yohimban-16-carboxylic acid, methyl ester Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(C(=O)OC)C(O)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 DNXIKVLOVZVMQF-UHFFFAOYSA-N 0.000 description 1
AAWZDTNXLSGCEK-LNVDRNJUSA-N (3r,5r)-1,3,4,5-tetrahydroxycyclohexane-1-carboxylic acid Chemical compound O[C@@H]1CC(O)(C(O)=O)C[C@@H](O)C1O AAWZDTNXLSGCEK-LNVDRNJUSA-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
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
- C07C211/26—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring
- C07C211/31—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring the six-membered aromatic ring being part of a condensed ring system formed by at least three rings
- 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
- C07C2603/22—Ortho- or ortho- and peri-condensed systems containing three rings containing only six-membered rings
- C07C2603/24—Anthracenes; Hydrogenated anthracenes
- 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)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Hydrogenated Pyridines (AREA)

NO538/72A 1971-02-23 1972-02-22 NO131594C (da)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
CH257771A CH552558A (de)	1971-02-23	1971-02-23	Verfahren zur herstellung neuer 9-(3-amino-1-propenyl)9,10-dihydro-9,10-aethano-anthracene.
CH68872A CH612805A5 (da)	1971-02-12	1972-01-17
CH66872		1972-01-17

Publications (2)

Publication Number	Publication Date
NO131594B true NO131594B (da)	1975-03-17
NO131594C NO131594C (da)	1975-06-25

Family

ID=27172295

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO538/72A NO131594C (da)	1971-02-23	1972-02-22

Country Status (19)

Country	Link
US (1)	US3862131A (da)
JP (1)	JPS5813534B1 (da)
AR (5)	AR203710A1 (da)
AT (1)	AT317193B (da)
BE (1)	BE779664A (da)
CA (1)	CA987318A (da)
CS (4)	CS174198B2 (da)
DD (1)	DD95388A5 (da)
DE (1)	DE2207212A1 (da)
ES (1)	ES400021A1 (da)
FR (1)	FR2126354B1 (da)
GB (1)	GB1383599A (da)
HU (1)	HU164398B (da)
IE (1)	IE36088B1 (da)
IL (1)	IL38772A (da)
NL (1)	NL7202325A (da)
NO (1)	NO131594C (da)
SE (1)	SE381458B (da)
SU (5)	SU472498A3 (da)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3965181A (en) *	1973-07-06	1976-06-22	Syntex (U.S.A.) Inc.	Tricyclic pharmacological agents, intermediates and methods of making
GB1508669A (en) *	1974-12-13	1978-04-26	Sumitomo Chemical Co	Methanoanthracene derivative and a process for the preparation thereof

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3489799A (en) *	1967-09-26	1970-01-13	Ciba Geigy Corp	Ethano-anthracenes

1972
- 1972-02-15 CA CA134,715A patent/CA987318A/en not_active Expired
- 1972-02-15 IL IL38772A patent/IL38772A/xx unknown
- 1972-02-16 IE IE191/72A patent/IE36088B1/xx unknown
- 1972-02-16 DE DE19722207212 patent/DE2207212A1/de not_active Ceased
- 1972-02-17 US US227277A patent/US3862131A/en not_active Expired - Lifetime
- 1972-02-18 GB GB762472A patent/GB1383599A/en not_active Expired
- 1972-02-18 SE SE7201993A patent/SE381458B/xx unknown
- 1972-02-21 ES ES400021A patent/ES400021A1/es not_active Expired
- 1972-02-22 SU SU1752589A patent/SU472498A3/ru active
- 1972-02-22 NL NL7202325A patent/NL7202325A/xx not_active Application Discontinuation
- 1972-02-22 AT AT143072A patent/AT317193B/de not_active IP Right Cessation
- 1972-02-22 NO NO538/72A patent/NO131594C/no unknown
- 1972-02-22 CS CS8641A patent/CS174198B2/cs unknown
- 1972-02-22 SU SU1952298A patent/SU510145A3/ru active
- 1972-02-22 CS CS8643A patent/CS174200B2/cs unknown
- 1972-02-22 SU SU1952304A patent/SU482941A3/ru active
- 1972-02-22 DD DD161039A patent/DD95388A5/xx unknown
- 1972-02-22 BE BE779664A patent/BE779664A/xx unknown
- 1972-02-22 CS CS8640A patent/CS174197B2/cs unknown
- 1972-02-22 HU HUCI1210A patent/HU164398B/hu unknown
- 1972-02-22 CS CS8642A patent/CS174199B2/cs unknown
- 1972-02-23 AR AR240667A patent/AR203710A1/es active
- 1972-02-23 JP JP47018165A patent/JPS5813534B1/ja active Pending
- 1972-02-23 FR FR7206116A patent/FR2126354B1/fr not_active Expired
1973
- 1973-01-01 AR AR246765A patent/AR203987A1/es active
- 1973-01-01 AR AR246763A patent/AR204157A1/es active
- 1973-02-23 AR AR246766A patent/AR201553A1/es active
- 1973-02-23 AR AR246764A patent/AR201658A1/es active
- 1973-07-27 SU SU1952306A patent/SU498901A3/ru active
- 1973-07-27 SU SU1952305A patent/SU502602A3/ru active

Also Published As

Publication number	Publication date
GB1383599A (en)	1974-02-12
SU472498A3 (ru)	1975-05-30
NO131594C (da)	1975-06-25
AR203987A1 (es)	1975-11-12
AR201553A1 (es)	1975-03-31
CS174200B2 (da)	1977-03-31
AR201658A1 (es)	1975-04-08
FR2126354A1 (da)	1972-10-06
AR204157A1 (es)	1975-11-28
IL38772A0 (en)	1972-04-27
CA987318A (en)	1976-04-13
NL7202325A (da)	1972-08-25
CS174198B2 (da)	1977-03-31
BE779664A (fr)	1972-08-22
ES400021A1 (es)	1975-09-01
IE36088B1 (en)	1976-08-18
AR203710A1 (es)	1975-10-15
CS174199B2 (da)	1977-03-31
SU482941A3 (ru)	1975-08-30
SE381458B (sv)	1975-12-08
SU502602A3 (ru)	1976-02-05
SU510145A3 (ru)	1976-04-05
IL38772A (en)	1975-06-25
HU164398B (da)	1974-02-28
DE2207212A1 (de)	1972-09-07
US3862131A (en)	1975-01-21
CS174197B2 (da)	1977-03-31
DD95388A5 (da)	1973-02-05
SU498901A3 (ru)	1976-01-05
FR2126354B1 (da)	1975-08-01
JPS5813534B1 (da)	1983-03-14
IE36088L (en)	1972-08-23
AT317193B (de)	1974-08-12

Publication	Publication Date	Title
IE51507B1 (en)	1987-01-07	Tricyclic imidazole derivatives
NO166164B (no)	1991-03-04	Festeanordning til aa etablere elektrisk forbindelse med en engangs hudelektrode.
NO884008L (no)	1989-03-10	Fremgangsmaate for fremstilling av 3,7-diazabicyclo(3,3,1)nonanforbindelser.
NO135140B (da)	1976-11-08
US4731470A (en)	1988-03-15	[(5,6-dichloro-3-oxo-2,9a-alkano-2,3,9,9a-tetrahydro-1H-fluoren-7-yl)oxy]alkanoic acids and alkanimidamides
US3933802A (en)	1976-01-20	New sulphamoylbenzoic acid amides
US4882353A (en)	1989-11-21	Chroman derivatives for combating thrombosis and asthma
US4203895A (en)	1980-05-20	Process for the preparation of cis-(±)-3,4-dihydro-N,N,2-trimethyl-2H-1-benzopyran-3-amine and intermediates produced thereby
NO170305B (no)	1992-06-22	Framgangsmaate og anordning for framstilling av isoleringslegeme
NO121893B (da)	1971-04-26
NO823587L (no)	1983-04-29	Laktoner.
NO163597B (no)	1990-03-19	Styreinnretning for et ett-eller tosporet kjoeretoey.
US3557127A (en)	1971-01-19	Substituted cyclohexenes,derivatives thereof and processes for obtaining same
US3255249A (en)	1966-06-07	2-branched lower alkyl-amino-1-(indan-, hydrogenated indan- and hydrogenated naphth-2-yl) lower alkanols
NO131594B (da)	1975-03-17
EP0118564B1 (en)	1987-04-22	4-amino-tetrahydro-2-naphthoic acid derivatives
US2906757A (en)	1959-09-29	Their preparation
NO814468L (no)	1982-07-01	Tiazolinderivater, fremgangsmaate til deres fremstilling, deres anvendelse samt farmasoeytiske preparater paa basis av disse forbindelser
US4017542A (en)	1977-04-12	9-(2-Hydroxy-3-amino-propyl)-9,10-dihydro-9,10-ethano-anthracenes and salts thereof
US4045580A (en)	1977-08-30	Pharmaceutical preparation using 9-(2-hydroxy-3-amino-propyl)-9,10-dihydro-9,10-ethano-anthracenes as antidepressants
EP0202950B1 (en)	1993-09-29	Berban derivatives and their preparation and pharmaceutical formulation
US3028394A (en)	1962-04-03	9-phenyl octahydroindole compounds and process of making same
DE1964797A1 (de)	1970-07-16	Neue Amine und Verfahren zu ihrer Herstellung
US2778829A (en)	1957-01-22	New 5:6-dihydro-benzo (c) cinnoline derivatives and a process for their preparation
NO136410B (da)	1977-05-23