NO792476L - Fremgangsmaate for fremstilling av organiske forbindelser - Google Patents

Fremgangsmaate for fremstilling av organiske forbindelser

Info

Publication number: NO792476L
Authority: NO; Norway
Prior art keywords: alkyl; compound; formula; benzyl; compounds
Prior art date: 1978-07-28

Application number

NO792476A

Other languages

English (en)

Norwegian (no)

Inventor

Regis Dupont

Patrick Lardenois

Claude Morel

Jonathan Frost

Gabor Istvan Koletar

Original Assignee

Synthelabo

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.)

1978-07-28

Filing date

1979-07-26

Publication date

1980-01-29

1978-07-28 Priority claimed from FR7822352A external-priority patent/FR2432025A1/fr

1978-07-28 Priority claimed from FR7822353A external-priority patent/FR2432026A1/fr

1979-07-26 Application filed by Synthelabo filed Critical Synthelabo

1980-01-29 Publication of NO792476L publication Critical patent/NO792476L/no

Links

238000000034 method Methods 0.000 title claims description 8
238000004519 manufacturing process Methods 0.000 title description 3
150000002894 organic compounds Chemical class 0.000 title 1
125000000217 alkyl group Chemical group 0.000 claims abstract description 23
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 16
125000002252 acyl group Chemical group 0.000 claims abstract description 14
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 13
239000001257 hydrogen Substances 0.000 claims abstract description 11
-1 halogenobenzyl Chemical group 0.000 claims abstract description 9
125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 8
125000001316 cycloalkyl alkyl group Chemical group 0.000 claims abstract description 8
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 8
150000002220 fluorenes Chemical class 0.000 claims abstract description 5
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims abstract description 4
125000006307 alkoxy benzyl group Chemical group 0.000 claims abstract description 3
125000006177 alkyl benzyl group Chemical group 0.000 claims abstract description 3
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 3
150000001875 compounds Chemical class 0.000 claims description 83
238000006243 chemical reaction Methods 0.000 claims description 8
238000002360 preparation method Methods 0.000 claims description 8
125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 7
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
150000002431 hydrogen Chemical class 0.000 claims description 5
125000003545 alkoxy group Chemical group 0.000 claims description 4
125000003435 aroyl group Chemical group 0.000 claims description 4
239000012948 isocyanate Substances 0.000 claims description 4
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 3
230000010933 acylation Effects 0.000 claims description 3
238000005917 acylation reaction Methods 0.000 claims description 3
230000029936 alkylation Effects 0.000 claims description 3
238000005804 alkylation reaction Methods 0.000 claims description 3
238000006264 debenzylation reaction Methods 0.000 claims description 3
150000008065 acid anhydrides Chemical class 0.000 claims description 2
230000002378 acidificating effect Effects 0.000 claims description 2
125000006277 halobenzyl group Chemical group 0.000 claims description 2
229910052736 halogen Inorganic materials 0.000 claims description 2
150000002367 halogens Chemical class 0.000 claims description 2
206010002660 Anoxia Diseases 0.000 abstract description 4
206010021143 Hypoxia Diseases 0.000 abstract description 4
150000003839 salts Chemical class 0.000 abstract description 3
239000002253 acid Substances 0.000 abstract description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 4
150000002219 fluoranthenes Chemical class 0.000 abstract 1
125000005843 halogen group Chemical group 0.000 abstract 1
239000004089 psychotropic agent Substances 0.000 abstract 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 65
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 44
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 36
239000000203 mixture Substances 0.000 description 24
239000000243 solution Substances 0.000 description 22
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 21
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 19
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 18
238000010992 reflux Methods 0.000 description 18
239000002904 solvent Substances 0.000 description 18
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 15
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
239000000155 melt Substances 0.000 description 15
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
238000001953 recrystallisation Methods 0.000 description 14
239000000047 product Substances 0.000 description 13
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
239000000725 suspension Substances 0.000 description 12
239000007787 solid Substances 0.000 description 11
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 9
RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 9
239000007858 starting material Substances 0.000 description 8
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 7
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
239000002244 precipitate Substances 0.000 description 7
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-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
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
238000001816 cooling Methods 0.000 description 6
238000001035 drying Methods 0.000 description 6
239000000706 filtrate Substances 0.000 description 6
239000012074 organic phase Substances 0.000 description 6
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
238000003756 stirring Methods 0.000 description 6
238000001704 evaporation Methods 0.000 description 5
230000008020 evaporation Effects 0.000 description 5
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
239000002585 base Substances 0.000 description 4
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 4
230000000694 effects Effects 0.000 description 4
LFTRYYFOMNLQNT-UHFFFAOYSA-N ethyl acetate;1h-indole Chemical compound CCOC(C)=O.C1=CC=C2NC=CC2=C1 LFTRYYFOMNLQNT-UHFFFAOYSA-N 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
APJYDQYYACXCRM-UHFFFAOYSA-N tryptamine Chemical compound C1=CC=C2C(CCN)=CNC2=C1 APJYDQYYACXCRM-UHFFFAOYSA-N 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
241000976983 Anoxia Species 0.000 description 3
241000699670 Mus sp. Species 0.000 description 3
239000007832 Na2SO4 Substances 0.000 description 3
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
229910021529 ammonia Inorganic materials 0.000 description 3
230000007953 anoxia Effects 0.000 description 3
238000009835 boiling Methods 0.000 description 3
239000013078 crystal Substances 0.000 description 3
238000001914 filtration Methods 0.000 description 3
150000004678 hydrides Chemical class 0.000 description 3
239000003208 petroleum Substances 0.000 description 3
239000000377 silicon dioxide Substances 0.000 description 3
229910052938 sodium sulfate Inorganic materials 0.000 description 3
235000011152 sodium sulphate Nutrition 0.000 description 3
XYGBKMMCQDZQOZ-UHFFFAOYSA-M sodium;4-hydroxybutanoate Chemical compound [Na+].OCCCC([O-])=O XYGBKMMCQDZQOZ-UHFFFAOYSA-M 0.000 description 3
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
230000004083 survival effect Effects 0.000 description 3
238000012360 testing method Methods 0.000 description 3
SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 description 2
JTEJPPKMYBDEMY-UHFFFAOYSA-N 5-methoxytryptamine Chemical compound COC1=CC=C2NC=C(CCN)C2=C1 JTEJPPKMYBDEMY-UHFFFAOYSA-N 0.000 description 2
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
241000700159 Rattus Species 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
150000001721 carbon Chemical group 0.000 description 2
239000002026 chloroform extract Substances 0.000 description 2
238000004090 dissolution Methods 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
239000012280 lithium aluminium hydride Substances 0.000 description 2
229910052760 oxygen Inorganic materials 0.000 description 2
239000001301 oxygen Substances 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
229910000027 potassium carbonate Inorganic materials 0.000 description 2
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
238000002390 rotary evaporation Methods 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
239000011734 sodium Substances 0.000 description 2
238000005406 washing Methods 0.000 description 2
HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 1
XIUUPSVCFNTVQZ-UHFFFAOYSA-N 1-(12-fluoro-3,5-dimethyl-1,3,6-triazatetracyclo[7.6.1.05,16.010,15]hexadeca-9(16),10(15),11,13-tetraen-6-yl)ethanone Chemical compound C12=CC(F)=CC=C2N2CN(C)CC3(C)N(C(C)=O)CCC1=C32 XIUUPSVCFNTVQZ-UHFFFAOYSA-N 0.000 description 1
ZKIORVIXEWIOGB-UHFFFAOYSA-N 2-(5-fluoro-1h-indol-3-yl)ethanamine Chemical compound C1=C(F)C=C2C(CCN)=CNC2=C1 ZKIORVIXEWIOGB-UHFFFAOYSA-N 0.000 description 1
IUUZMSMGSOUFTO-UHFFFAOYSA-N 2-indol-1-ylacetamide Chemical compound C1=CC=C2N(CC(=O)N)C=CC2=C1 IUUZMSMGSOUFTO-UHFFFAOYSA-N 0.000 description 1
229940097276 5-methoxytryptamine Drugs 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
208000020401 Depressive disease Diseases 0.000 description 1
229910010082 LiAlH Inorganic materials 0.000 description 1
229910010084 LiAlH4 Inorganic materials 0.000 description 1
RWBIPOOOLDZZBY-UHFFFAOYSA-N N1C(C=C2C(C=CC=C12)=O)=O Chemical compound N1C(C=C2C(C=CC=C12)=O)=O RWBIPOOOLDZZBY-UHFFFAOYSA-N 0.000 description 1
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
208000003443 Unconsciousness Diseases 0.000 description 1
208000027418 Wounds and injury Diseases 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
239000000654 additive Substances 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
238000010171 animal model Methods 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
230000003542 behavioural effect Effects 0.000 description 1
230000006931 brain damage Effects 0.000 description 1
231100000874 brain damage Toxicity 0.000 description 1
208000029028 brain injury Diseases 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
230000002490 cerebral effect Effects 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
229910052681 coesite Inorganic materials 0.000 description 1
230000001054 cortical effect Effects 0.000 description 1
229910052906 cristobalite Inorganic materials 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
230000006378 damage Effects 0.000 description 1
230000003001 depressive effect Effects 0.000 description 1
150000005690 diesters Chemical class 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
238000004821 distillation Methods 0.000 description 1
230000000517 effect on sleep Effects 0.000 description 1
238000010828 elution Methods 0.000 description 1
239000012259 ether extract Substances 0.000 description 1
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000006260 foam Substances 0.000 description 1
239000008098 formaldehyde solution Substances 0.000 description 1
239000012458 free base Substances 0.000 description 1
239000011521 glass Substances 0.000 description 1
RERZNCLIYCABFS-UHFFFAOYSA-N harmaline Chemical compound C1CN=C(C)C2=C1C1=CC=C(OC)C=C1N2 RERZNCLIYCABFS-UHFFFAOYSA-N 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
238000007327 hydrogenolysis reaction Methods 0.000 description 1
KDFBGNBTTMPNIG-UHFFFAOYSA-N hydron;2-(1h-indol-3-yl)ethanamine;chloride Chemical compound Cl.C1=CC=C2C(CCN)=CNC2=C1 KDFBGNBTTMPNIG-UHFFFAOYSA-N 0.000 description 1
208000014674 injury Diseases 0.000 description 1
238000007912 intraperitoneal administration Methods 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
150000002513 isocyanates Chemical class 0.000 description 1
239000007937 lozenge Substances 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
229910052753 mercury Inorganic materials 0.000 description 1
CWKLZLBVOJRSOM-UHFFFAOYSA-N methyl pyruvate Chemical compound COC(=O)C(C)=O CWKLZLBVOJRSOM-UHFFFAOYSA-N 0.000 description 1
125000004674 methylcarbonyl group Chemical group CC(=O)* 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
KHPXUQMNIQBQEV-UHFFFAOYSA-L oxaloacetate(2-) Chemical compound [O-]C(=O)CC(=O)C([O-])=O KHPXUQMNIQBQEV-UHFFFAOYSA-L 0.000 description 1
238000006213 oxygenation reaction Methods 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
235000010603 pastilles Nutrition 0.000 description 1
239000012071 phase Substances 0.000 description 1
230000000506 psychotropic effect Effects 0.000 description 1
230000029058 respiratory gaseous exchange Effects 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
230000007017 scission Effects 0.000 description 1
239000013049 sediment Substances 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
210000003625 skull Anatomy 0.000 description 1
230000004617 sleep duration Effects 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
ZVCDLGYNFYZZOK-UHFFFAOYSA-M sodium cyanate Chemical compound [Na]OC#N ZVCDLGYNFYZZOK-UHFFFAOYSA-M 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
JPTKZRPOIUYFTM-UHFFFAOYSA-N sodium;diethyl 2-oxobutanedioate Chemical compound [Na+].CCOC(=O)[CH-]C(=O)C(=O)OCC JPTKZRPOIUYFTM-UHFFFAOYSA-N 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
229910052682 stishovite Inorganic materials 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
230000000287 tissue oxygenation Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 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
229910052905 tridymite Inorganic materials 0.000 description 1
238000001665 trituration Methods 0.000 description 1
208000009999 tuberous sclerosis Diseases 0.000 description 1
230000002792 vascular Effects 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains three hetero rings
- C07D471/14—Ortho-condensed systems

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)
Nitrogen Condensed Heterocyclic Rings (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Steroid Compounds (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Medicinal Preparation (AREA)

NO792476A 1978-07-28 1979-07-26 Fremgangsmaate for fremstilling av organiske forbindelser NO792476L (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
FR7822352A FR2432025A1 (fr)	1978-07-28	1978-07-28	Derives d'imidazo et de pyrimido-pyrido-indoles, leur preparation et leur application en therapeutique
FR7822353A FR2432026A1 (fr)	1978-07-28	1978-07-28	Derives de fluorenes et de fluoranthenes et leur application en therapeutique

Publications (1)

Publication Number	Publication Date
NO792476L true NO792476L (no)	1980-01-29

Family

ID=26220699

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO792476A NO792476L (no)	1978-07-28	1979-07-26	Fremgangsmaate for fremstilling av organiske forbindelser

Country Status (13)

Country	Link
US (1)	US4277476A (de)
EP (1)	EP0008249B1 (de)
AT (1)	ATE165T1 (de)
AU (1)	AU524307B2 (de)
CA (1)	CA1107729A (de)
DE (1)	DE2960689D1 (de)
DK (1)	DK316279A (de)
ES (1)	ES482889A1 (de)
FI (1)	FI65250C (de)
GR (1)	GR75070B (de)
NO (1)	NO792476L (de)
NZ (1)	NZ191141A (de)
PT (1)	PT69988A (de)

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US4428880A (en)	1981-05-04	1984-01-31	S.A. Omnichem	Azepino[4,5-d]indole derivatives and preparation thereof
GB2184685B (en) *	1985-12-19	1989-10-11	Braas & Co Gmbh	Plastically deformable sheet material
EP2147679B1 (de)	2001-07-25	2014-06-25	Raptor Pharmaceutical, Inc.	Zusammensetzungen für den Blut-Hirn-Schrankentransport
US7767689B2 (en)	2004-03-15	2010-08-03	Ptc Therapeutics, Inc.	Carboline derivatives useful in the treatment of cancer
ZA200608176B (en)	2004-03-15	2008-05-28	Ptc Therapeutics Inc	Carboline derivatives useful in the inhibition of angiogenesis
US8076352B2 (en)	2004-03-15	2011-12-13	Ptc Therapeutics, Inc.	Administration of carboline derivatives useful in the treatment of cancer and other diseases
US8076353B2 (en)	2004-03-15	2011-12-13	Ptc Therapeutics, Inc.	Inhibition of VEGF translation
EP2392258B1 (de)	2005-04-28	2014-10-08	Proteus Digital Health, Inc.	Pharma-Informatiksystem
CN101594878A (zh)	2006-09-18	2009-12-02	雷普特药品公司	通过给予受体相关蛋白（rap）-缀合物对肝病症的治疗
PL3395372T3 (pl)	2009-02-20	2022-07-25	EnhanX Biopharm Inc.	Układ do dostarczania leków na bazie glutationu
CN102458374A (zh)	2009-05-06	2012-05-16	实验室护肤股份有限公司	包含活性剂-磷酸钙颗粒复合物的皮肤递送组合物及其使用方法
US20120077778A1 (en)	2010-09-29	2012-03-29	Andrea Bourdelais	Ladder-Frame Polyether Conjugates

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US2556574A (en) *	1949-06-24	1951-06-12	Allen & Hanburys Ltd	Indolopteridines and process for preparing same
US3108108A (en) *	1959-09-25	1963-10-22	Bayer Ag	Aza analogues of polynuclear o-quinones
US3122544A (en) *	1962-11-13	1964-02-25	American Home Prod	4-amino-2-aryl-6h-indeno(2, 3-g)-pteridin-6-ones
US3470181A (en) *	1967-10-23	1969-09-30	American Home Prod	Fused 2-pyrimidinepropionic acid compounds,related compounds,and the process for their preparation
US3631046A (en) *	1969-05-28	1971-12-28	Sandoz Ag	Tetracyclic quinazolin-ones
BE759337A (fr) *	1969-11-24	1971-05-24	Lilly Co Eli	Benzimidazol (2,1-b)-quinazolin (6h) ones qui sont des immuno-depresseurs, et nouvelles benzimidazo (2,1-b) quinazolin-12-(6h) ones
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1979
- 1979-07-05 EP EP79400459A patent/EP0008249B1/de not_active Expired
- 1979-07-05 DE DE7979400459T patent/DE2960689D1/de not_active Expired
- 1979-07-05 AT AT79400459T patent/ATE165T1/de not_active IP Right Cessation
- 1979-07-26 CA CA332,589A patent/CA1107729A/en not_active Expired
- 1979-07-26 DK DK316279A patent/DK316279A/da not_active Application Discontinuation
- 1979-07-26 US US06/060,857 patent/US4277476A/en not_active Expired - Lifetime
- 1979-07-26 PT PT69988A patent/PT69988A/pt unknown
- 1979-07-26 AU AU49278/79A patent/AU524307B2/en not_active Ceased
- 1979-07-26 NO NO792476A patent/NO792476L/no unknown
- 1979-07-27 ES ES482889A patent/ES482889A1/es not_active Expired
- 1979-07-27 NZ NZ191141A patent/NZ191141A/xx unknown
- 1979-07-27 FI FI792366A patent/FI65250C/fi not_active IP Right Cessation
1981
- 1981-01-05 GR GR59709A patent/GR75070B/el unknown

Also Published As

Publication number	Publication date
PT69988A (fr)	1979-08-01
ATE165T1 (de)	1981-09-15
DK316279A (da)	1980-01-29
EP0008249A2 (de)	1980-02-20
FI65250C (fi)	1984-04-10
FI65250B (fi)	1983-12-30
AU524307B2 (en)	1982-09-09
CA1107729A (en)	1981-08-25
EP0008249A3 (en)	1980-05-14
FI792366A7 (fi)	1980-01-29
NZ191141A (en)	1983-02-15
US4277476A (en)	1981-07-07
DE2960689D1 (en)	1981-11-19
ES482889A1 (es)	1980-04-16
AU4927879A (en)	1980-01-31
GR75070B (de)	1984-07-13
EP0008249B1 (de)	1981-08-26

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DK174161B1 (da)	2002-07-29	Anellerede indolderivater, fremgangsmåde til deres fremstilling og fremgangsmåde til fremstilling af farmaceutisk præparat indeholdende dem
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EA020409B1 (ru)	2014-10-30	Антагонисты рецептора cgrp
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SU1644718A3 (ru)	1991-04-23	Способ получени производных пиразоло[3,4- @ ]хинолина или пиридо [2,3- @ ]хиназолина или их солей
WO1994007859A1 (en)	1994-04-14	5-ht4 antagonists
NO134212B (de)	1976-05-24
EP1078928A1 (de)	2001-02-28	Pyridinderivate, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Zubereitungen
EP0021857B1 (de)	1982-12-22	Indolderivate, ihre Herstellung und diese Verbindungen enthaltende Arzneimittel
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NO794271L (no)	1980-10-28	Fremgangsmaate for fremstilling av indol-dioner
NO167863B (no)	1991-09-09	Analogifremgangsmaate til fremstilling av terapeutisk aktive, kondenserte, heterocykliske tetrahydroaminokinolinoler.
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CA2317515A1 (en)	1999-08-05	Oxazole derivatives as serotonin-1a receptor agonists
DK153149B (da)	1988-06-20	Analogifremgangsmaade til fremstilling af hydroxyaminoeburnanderivater eller farmaceutisk acceptable syreadditionssalte eller optisk aktiv isomerer deraf, samt octahydroindolokinolizin-monoesterderivater til anvendelse som udgangsmateriale ved fremgangsmaaden
NO157578B (no)	1988-01-04	Analogifremgangsmaate ved fremstilling av terapeutisk aktive imidazo(1,2-a)kinolinderivater
CA1277319C (en)	1990-12-04	5-aminoalkyl-beta-carboline derivatives, their production and their use as drugs
US3862160A (en)	1975-01-21	Derivatives of 9h-pyrido(3,4-b) indole and process of preparation
CA1300146C (en)	1992-05-05	12b-substituted 1-hydroxymethyl-octahydroindolo¬2,3-a\|- quinolizine derivatives, process for the preparation and pharmaceutical compositions containing them
EP0120832B1 (de)	1987-04-29	4-Alkylindolonaphthyridine und diese enthaltende pharmazeutische Zubereitungen
US4803207A (en)	1989-02-07	Hypoglycemic 2',3',10'-tetrahydro-10'-hydroxy-10'-substituted-spiro[cycloakane-1,3'-pyrimido(1,2-a)indole]deratives
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