CH544066A - Verfahren zur Herstellung von Fluorenverbindungen - Google Patents

Verfahren zur Herstellung von Fluorenverbindungen

Info

Publication number: CH544066A
Authority: CH; Switzerland
Prior art keywords: sep; alkyl; formula; hydrogen; compounds
Prior art date: 1966-11-14

Application number

CH1590567A

Other languages

German (de)

English (en)

Inventor

Frank Hayes Norman

Original Assignee

Allen & Hanburys Ltd

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1966-11-14

Filing date

1967-11-14

Publication date

1973-11-15

1967-11-14 Application filed by Allen & Hanburys Ltd filed Critical Allen & Hanburys Ltd

1973-11-15 Publication of CH544066A publication Critical patent/CH544066A/de

Links

NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 title abstract description 6
230000003110 anti-inflammatory effect Effects 0.000 title abstract description 5
230000001773 anti-convulsant effect Effects 0.000 title abstract description 4
239000001961 anticonvulsive agent Substances 0.000 title abstract description 4
229960003965 antiepileptics Drugs 0.000 title abstract description 4
-1 sulphonamido Chemical group 0.000 claims abstract description 28
125000000217 alkyl group Chemical group 0.000 claims abstract description 10
125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 claims abstract description 7
150000003839 salts Chemical class 0.000 claims abstract description 6
239000002253 acid Substances 0.000 claims abstract description 5
125000005842 heteroatom Chemical group 0.000 claims abstract description 5
125000002947 alkylene group Chemical group 0.000 claims abstract description 4
125000003118 aryl group Chemical group 0.000 claims abstract description 4
125000002252 acyl group Chemical group 0.000 claims abstract description 3
125000003545 alkoxy group Chemical group 0.000 claims abstract description 3
125000006264 diethylaminomethyl group Chemical group [H]C([H])([H])C([H])([H])N(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 claims abstract description 3
229910052736 halogen Inorganic materials 0.000 claims abstract description 3
150000002367 halogens Chemical class 0.000 claims abstract description 3
125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract description 3
125000001064 morpholinomethyl group Chemical group [H]C([H])(*)N1C([H])([H])C([H])([H])OC([H])([H])C1([H])[H] 0.000 claims abstract description 3
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 3
125000004953 trihalomethyl group Chemical group 0.000 claims abstract description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 2
150000001875 compounds Chemical class 0.000 claims description 25
229910052739 hydrogen Inorganic materials 0.000 claims description 14
239000001257 hydrogen Substances 0.000 claims description 14
238000000034 method Methods 0.000 claims description 14
125000004432 carbon atom Chemical group C* 0.000 claims description 8
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 8
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
238000002360 preparation method Methods 0.000 claims description 6
239000003054 catalyst Substances 0.000 claims description 5
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
150000001412 amines Chemical class 0.000 claims description 3
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
238000006243 chemical reaction Methods 0.000 claims description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
238000007327 hydrogenolysis reaction Methods 0.000 claims description 2
229910052987 metal hydride Inorganic materials 0.000 claims description 2
150000004681 metal hydrides Chemical class 0.000 claims description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 claims description 2
125000003368 amide group Chemical group 0.000 claims 1
150000003141 primary amines Chemical class 0.000 claims 1
230000000202 analgesic effect Effects 0.000 abstract description 4
230000001078 anti-cholinergic effect Effects 0.000 abstract description 4
230000001430 anti-depressive effect Effects 0.000 abstract description 3
239000000935 antidepressant agent Substances 0.000 abstract description 3
229940005513 antidepressants Drugs 0.000 abstract description 3
230000000694 effects Effects 0.000 abstract description 3
BCGWQEUPMDMJNV-UHFFFAOYSA-N imipramine Chemical compound C1CC2=CC=CC=C2N(CCCN(C)C)C2=CC=CC=C21 BCGWQEUPMDMJNV-UHFFFAOYSA-N 0.000 abstract description 3
229960004801 imipramine Drugs 0.000 abstract description 3
125000003435 aroyl group Chemical group 0.000 abstract description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 35
OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 32
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
230000008018 melting Effects 0.000 description 15
238000002844 melting Methods 0.000 description 15
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
238000005303 weighing Methods 0.000 description 11
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
239000000203 mixture Substances 0.000 description 8
229910001868 water Inorganic materials 0.000 description 8
125000004005 formimidoyl group Chemical group [H]\N=C(/[H])* 0.000 description 7
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 6
239000000126 substance Substances 0.000 description 6
150000002220 fluorenes Chemical class 0.000 description 5
150000002431 hydrogen Chemical group 0.000 description 5
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 5
229910000041 hydrogen chloride Inorganic materials 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
238000002347 injection Methods 0.000 description 4
239000007924 injection Substances 0.000 description 4
238000010992 reflux Methods 0.000 description 4
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
238000004220 aggregation Methods 0.000 description 3
230000002776 aggregation Effects 0.000 description 3
150000001408 amides Chemical class 0.000 description 3
239000013078 crystal Substances 0.000 description 3
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 3
239000003814 drug Substances 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
GQNUPLZPYCRVRN-UHFFFAOYSA-N n-(9h-fluoren-9-yl)-n',n'-dimethylethane-1,2-diamine Chemical compound C1=CC=C2C(NCCN(C)C)C3=CC=CC=C3C2=C1 GQNUPLZPYCRVRN-UHFFFAOYSA-N 0.000 description 3
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
239000000047 product Substances 0.000 description 3
238000001953 recrystallisation Methods 0.000 description 3
239000000243 solution Substances 0.000 description 3
239000000725 suspension Substances 0.000 description 3
125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
OUGMRQJTULXVDC-UHFFFAOYSA-N 9h-fluoren-9-amine Chemical compound C1=CC=C2C(N)C3=CC=CC=C3C2=C1 OUGMRQJTULXVDC-UHFFFAOYSA-N 0.000 description 2
VGENDFBAVYCEFN-UHFFFAOYSA-N CN(C)CCN(C)C1C2=CC=CC=C2C2=C1C=CC=C2 Chemical compound CN(C)CCN(C)C1C2=CC=CC=C2C2=C1C=CC=C2 VGENDFBAVYCEFN-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
241000699670 Mus sp. Species 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
UCTWMZQNUQWSLP-UHFFFAOYSA-N adrenaline Chemical compound CNCC(O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-UHFFFAOYSA-N 0.000 description 2
210000000601 blood cell Anatomy 0.000 description 2
150000004985 diamines Chemical class 0.000 description 2
229940079593 drug Drugs 0.000 description 2
QMEZUZOCLYUADC-UHFFFAOYSA-N hydrate;dihydrochloride Chemical compound O.Cl.Cl QMEZUZOCLYUADC-UHFFFAOYSA-N 0.000 description 2
230000002631 hypothermal effect Effects 0.000 description 2
CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 2
238000007914 intraventricular administration Methods 0.000 description 2
239000007788 liquid Substances 0.000 description 2
229910052943 magnesium sulfate Inorganic materials 0.000 description 2
235000019341 magnesium sulphate Nutrition 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
239000013081 microcrystal Substances 0.000 description 2
BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 2
DILRJUIACXKSQE-UHFFFAOYSA-N n',n'-dimethylethane-1,2-diamine Chemical compound CN(C)CCN DILRJUIACXKSQE-UHFFFAOYSA-N 0.000 description 2
230000002093 peripheral effect Effects 0.000 description 2
239000003208 petroleum Substances 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
239000007787 solid Substances 0.000 description 2
239000002904 solvent Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 2
SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 description 1
WRRSFOZOETZUPG-FFHNEAJVSA-N (4r,4ar,7s,7ar,12bs)-9-methoxy-3-methyl-2,4,4a,7,7a,13-hexahydro-1h-4,12-methanobenzofuro[3,2-e]isoquinoline-7-ol;hydrate Chemical compound O.C([C@H]1[C@H](N(CC[C@@]112)C)C3)=C[C@H](O)[C@@H]1OC1=C2C3=CC=C1OC WRRSFOZOETZUPG-FFHNEAJVSA-N 0.000 description 1
VRZZMRYGHFNKEN-UHFFFAOYSA-N 2-(4-methylpiperazin-1-yl)acetamide Chemical compound CN1CCN(CC(N)=O)CC1 VRZZMRYGHFNKEN-UHFFFAOYSA-N 0.000 description 1
UNKLFUFMFMAYMX-UHFFFAOYSA-N 2-(9h-fluoren-9-ylamino)-n,n-dimethylacetamide Chemical compound C1=CC=C2C(NCC(=O)N(C)C)C3=CC=CC=C3C2=C1 UNKLFUFMFMAYMX-UHFFFAOYSA-N 0.000 description 1
NAHKTZOMFDGCMO-UHFFFAOYSA-N 2-(9h-fluoren-9-ylamino)acetamide Chemical compound C1=CC=C2C(NCC(=O)N)C3=CC=CC=C3C2=C1 NAHKTZOMFDGCMO-UHFFFAOYSA-N 0.000 description 1
XBPPLECAZBTMMK-UHFFFAOYSA-N 2-chloro-n,n-dimethylacetamide Chemical compound CN(C)C(=O)CCl XBPPLECAZBTMMK-UHFFFAOYSA-N 0.000 description 1
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 1
XTWYTFMLZFPYCI-KQYNXXCUSA-N 5'-adenylphosphoric acid Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O XTWYTFMLZFPYCI-KQYNXXCUSA-N 0.000 description 1
AHCDKANCCBEQJJ-UHFFFAOYSA-N 9-bromo-9h-fluorene Chemical compound C1=CC=C2C(Br)C3=CC=CC=C3C2=C1 AHCDKANCCBEQJJ-UHFFFAOYSA-N 0.000 description 1
XTWYTFMLZFPYCI-UHFFFAOYSA-N Adenosine diphosphate Natural products C1=NC=2C(N)=NC=NC=2N1C1OC(COP(O)(=O)OP(O)(O)=O)C(O)C1O XTWYTFMLZFPYCI-UHFFFAOYSA-N 0.000 description 1
201000001320 Atherosclerosis Diseases 0.000 description 1
RENMDAKOXSCIGH-UHFFFAOYSA-N Chloroacetonitrile Chemical compound ClCC#N RENMDAKOXSCIGH-UHFFFAOYSA-N 0.000 description 1
102000008186 Collagen Human genes 0.000 description 1
108010035532 Collagen Proteins 0.000 description 1
BWLUMTFWVZZZND-UHFFFAOYSA-N Dibenzylamine Chemical compound C=1C=CC=CC=1CNCC1=CC=CC=C1 BWLUMTFWVZZZND-UHFFFAOYSA-N 0.000 description 1
208000029422 Hypernatremia Diseases 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
208000006550 Mydriasis Diseases 0.000 description 1
UQQMQKFQFXRRSO-UHFFFAOYSA-N N-[2-(fluoren-9-ylideneamino)ethyl]acetamide Chemical compound C(C)(=O)NCCN=C1C2=CC=CC=C2C=2C=CC=CC12 UQQMQKFQFXRRSO-UHFFFAOYSA-N 0.000 description 1
UIQMVEYFGZJHCZ-SSTWWWIQSA-N Nalorphine Chemical compound C([C@@H](N(CC1)CC=C)[C@@H]2C=C[C@@H]3O)C4=CC=C(O)C5=C4[C@@]21[C@H]3O5 UIQMVEYFGZJHCZ-SSTWWWIQSA-N 0.000 description 1
RSDOPYMFZBJHRL-UHFFFAOYSA-N Oxotremorine Chemical compound O=C1CCCN1CC#CCN1CCCC1 RSDOPYMFZBJHRL-UHFFFAOYSA-N 0.000 description 1
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium on carbon Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
229940123445 Tricyclic antidepressant Drugs 0.000 description 1
208000013521 Visual disease Diseases 0.000 description 1
101100082032 Xenopus laevis pou3f1-a gene Proteins 0.000 description 1
AXJDEHNQPMZKOS-UHFFFAOYSA-N acetylazanium;chloride Chemical compound [Cl-].CC([NH3+])=O AXJDEHNQPMZKOS-UHFFFAOYSA-N 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
239000000654 additive Substances 0.000 description 1
230000004931 aggregating effect Effects 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
230000001760 anti-analgesic effect Effects 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
239000002585 base Substances 0.000 description 1
230000004071 biological effect Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
235000010418 carrageenan Nutrition 0.000 description 1
229920001525 carrageenan Polymers 0.000 description 1
239000000969 carrier Substances 0.000 description 1
210000003169 central nervous system Anatomy 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
239000002026 chloroform extract Substances 0.000 description 1
239000000812 cholinergic antagonist Substances 0.000 description 1
239000011247 coating layer Substances 0.000 description 1
OROGSEYTTFOCAN-DNJOTXNNSA-N codeine Natural products C([C@H]1[C@H](N(CC[C@@]112)C)C3)=C[C@H](O)[C@@H]1OC1=C2C3=CC=C1OC OROGSEYTTFOCAN-DNJOTXNNSA-N 0.000 description 1
229960004126 codeine Drugs 0.000 description 1
229920001436 collagen Polymers 0.000 description 1
208000029078 coronary artery disease Diseases 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
206010013781 dry mouth Diseases 0.000 description 1
238000001035 drying Methods 0.000 description 1
LBAQSKZHMLAFHH-UHFFFAOYSA-N ethoxyethane;hydron;chloride Chemical compound Cl.CCOCC LBAQSKZHMLAFHH-UHFFFAOYSA-N 0.000 description 1
125000006534 ethyl amino methyl group Chemical group [H]N(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
238000001914 filtration Methods 0.000 description 1
YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
238000009472 formulation Methods 0.000 description 1
239000012458 free base Substances 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
150000002366 halogen compounds Chemical class 0.000 description 1
LIAWOTKNAVAKCX-UHFFFAOYSA-N hydrazine;dihydrochloride Chemical compound Cl.Cl.NN LIAWOTKNAVAKCX-UHFFFAOYSA-N 0.000 description 1
238000006698 hydrazinolysis reaction Methods 0.000 description 1
OROGSEYTTFOCAN-UHFFFAOYSA-N hydrocodone Natural products C1C(N(CCC234)C)C2C=CC(O)C3OC2=C4C1=CC=C2OC OROGSEYTTFOCAN-UHFFFAOYSA-N 0.000 description 1
125000004356 hydroxy functional group Chemical group O* 0.000 description 1
229960000905 indomethacin Drugs 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
208000028774 intestinal disease Diseases 0.000 description 1
238000002955 isolation Methods 0.000 description 1
JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 1
229940011051 isopropyl acetate Drugs 0.000 description 1
239000010410 layer Substances 0.000 description 1
239000012280 lithium aluminium hydride Substances 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
BCUMPULZWNQMKD-UHFFFAOYSA-N methanol;propan-2-yl acetate Chemical compound OC.CC(C)OC(C)=O BCUMPULZWNQMKD-UHFFFAOYSA-N 0.000 description 1
150000004682 monohydrates Chemical class 0.000 description 1
229960005181 morphine Drugs 0.000 description 1
DAKZISABEDGGSV-UHFFFAOYSA-N n-(2-aminoethyl)acetamide Chemical compound CC(=O)NCCN DAKZISABEDGGSV-UHFFFAOYSA-N 0.000 description 1
OEQTYNBNMMKNDY-UHFFFAOYSA-N n-chloro-9h-fluoren-9-amine Chemical compound C1=CC=C2C(NCl)C3=CC=CC=C3C2=C1 OEQTYNBNMMKNDY-UHFFFAOYSA-N 0.000 description 1
229960000938 nalorphine Drugs 0.000 description 1
239000004084 narcotic analgesic agent Substances 0.000 description 1
229910000510 noble metal Inorganic materials 0.000 description 1
229960002748 norepinephrine Drugs 0.000 description 1
SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
239000012071 phase Substances 0.000 description 1
229960002895 phenylbutazone Drugs 0.000 description 1
VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 description 1
XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
125000006239 protecting group Chemical group 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
230000000638 stimulation Effects 0.000 description 1
229960002317 succinimide Drugs 0.000 description 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
239000003029 tricyclic antidepressant agent Substances 0.000 description 1
208000029257 vision disease Diseases 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
- C07C237/22—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton having nitrogen atoms of amino groups bound to the carbon skeleton of the acid part, further acylated
- 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
- C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
- C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
- C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
- C07C2603/18—Fluorenes; Hydrogenated fluorenes

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

CH1590567A 1966-11-14 1967-11-14 Verfahren zur Herstellung von Fluorenverbindungen CH544066A (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB50980/66A GB1176173A (en)	1966-11-14	1966-11-14	Novel Fluorene Compounds

Publications (1)

Publication Number	Publication Date
CH544066A true CH544066A (de)	1973-11-15

Family

ID=10458167

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH1590567A CH544066A (de)	1966-11-14	1967-11-14	Verfahren zur Herstellung von Fluorenverbindungen

Country Status (6)

Country	Link
BE (1)	BE706262A (fr)
CH (1)	CH544066A (fr)
FR (1)	FR8389M (fr)
GB (1)	GB1176173A (fr)
LU (1)	LU54842A1 (fr)
NL (1)	NL6715385A (fr)

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DK575387A (da) *	1986-11-04	1988-05-05	Otsuka Pharma Co Ltd	Hydrofluorenderivater, fremgangsmaade til fremstilling deraf og praeparater indeholdende saadanne forbindelser
US4837226A (en) *	1988-04-27	1989-06-06	Warner-Lambert Company	Polycyclic amine derivatives useful as cerebrovascular agents
US5278191A (en) *	1988-08-31	1994-01-11	G. D. Searle & Co.	Diphenylmethylaminoacetamide derivatives as anti-convulsants
US5288905A (en) *	1988-10-07	1994-02-22	G. D. Searle & Co.	Glycyl urea derivatives as anti-convulsants
US5098916A (en) *	1990-03-29	1992-03-24	G. D. Searle & Co.	Propanobicyclic amine derivatives for cns disorders
US5089506A (en) *	1990-04-30	1992-02-18	G. D. Searle & Co.	Ethanobicyclic amine derivatives for cns disorders
US5215992A (en) *	1990-04-30	1993-06-01	G. D. Searle & Co.	Ethanobicyclic amine derivatives for CNS disorders
US5141960A (en) *	1991-06-25	1992-08-25	G. D. Searle & Co.	Tricyclic glycinamide derivatives as anti-convulsants
AU5271996A (en) *	1995-04-07	1996-10-23	Novo Nordisk A/S	Novel heterocyclic compounds
WO1996031474A1 (fr) *	1995-04-07	1996-10-10	Novo Nordisk A/S	Nouveaux composes heterocycliques
AU5271796A (en) *	1995-04-07	1996-10-23	Novo Nordisk A/S	Novel heterocyclic compounds
WO1996031503A1 (fr) *	1995-04-07	1996-10-10	Novo Nordisk A/S	Nouveaux composes heterocycliques
US5952352A (en) *	1995-04-07	1999-09-14	Novo Nordisk A/S	Heterocyclic compounds

1966
- 1966-11-14 GB GB50980/66A patent/GB1176173A/en not_active Expired
1967
- 1967-11-09 BE BE706262D patent/BE706262A/xx unknown
- 1967-11-10 LU LU54842D patent/LU54842A1/xx unknown
- 1967-11-13 NL NL6715385A patent/NL6715385A/xx unknown
- 1967-11-14 FR FR128015A patent/FR8389M/fr not_active Expired
- 1967-11-14 CH CH1590567A patent/CH544066A/de not_active IP Right Cessation

Also Published As

Publication number	Publication date
LU54842A1 (fr)	1968-02-02
GB1176173A (en)	1970-01-01
FR8389M (fr)	1971-03-31
NL6715385A (fr)	1968-05-15
BE706262A (fr)	1968-05-09

Legal Events

Date	Code	Title	Description
1976-06-15	PL	Patent ceased

Publication	Publication Date	Title
DE2634288C3 (fr)	1980-03-13
DE1770153C3 (de)	1979-08-30	Heterocyclische Aminoketone, deren pharmakologisch verträgliche Säureadditionssalze und Verfahren zu ihrer Herstellung
CH544066A (de)	1973-11-15	Verfahren zur Herstellung von Fluorenverbindungen
DE69625877T2 (de)	2003-12-24	Verwendung von 5-HT1A Rezeptor-Liganden zur Behandlung des Glaukoms
DE2163911B2 (de)	1974-02-28	2-Aminomethyl-phenole, Verfahren zur Herstellung derselben und diese enthaltende Arzneimittel
DE2727047A1 (de)	1977-12-29	Indol-derivate, verfahren zu deren herstellung und diese enthaltende pharmazeutische praeparate
DE2460929C2 (fr)	1987-12-17
DE3233424A1 (de)	1984-03-15	Isochinolinderivate, verfahren zu ihrer herstellung, pharmazeutische praeparate auf basis dieser verbindungen und ihre verwendung
DE1695111B1 (de)	1972-05-31	Indolderivate
DE3112984A1 (de)	1981-12-24	2-(3-(4-(3-chlor-4-fluorphenyl)-1-piperazinyl) propyl)-1,2,4-triazolo(4,3-a)pyridin-3(2h)-on dessen pharmazeutische anwendung und herstellung
DE2503136A1 (de)	1975-07-31	5-methylthiopyrimidine, die als antidiabetische und hypocholesterinaemische arzneimittel geeignet sind
DE2746550C2 (fr)	1987-10-15
DE2621082C2 (de)	1986-02-13	Piperazinderivat, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel
DE2034640C3 (de)	1980-06-12	l-p-(7-Trifluormethyl-4-chinolyl) -amino-benzoyl-piperazine, Verfahren zu ihrer Herstellung und ihre Verwendung bei der Bekämpfung von Bluthochdruck
DE2931319A1 (de)	1980-02-14	6-methoxy-2-acetylnaphthalinoxim- derivate, verfahren zu ihrer herstellung sowie sie enthaltende arzneimittel
DE2062055C3 (de)	1979-01-18	Propanolamin-Derivate, Verfahren zu ihrer Herstellung und sie enthaltende Arzneimittel
DE2654888A1 (de)	1977-06-08	Diphenylacetamide, verfahren zu ihrer herstellung und sie enthaltende arzneimittel
DE2755707A1 (de)	1978-06-29	Verfahren zur herstellung von neuen piperazinderivaten
DE2063901A1 (en)	1972-07-20	Phenylalkylaminoalkylthiazoles - as antiphlogistics
DE2754148A1 (de)	1978-06-08	Substituierte aminoaethanole, verfahren zu ihrer herstellung und ihre verwendung als arzneistoffe
DE2810052A1 (de)	1978-09-14	Aminoaryl-1,2,4-triazine, verfahren zu ihrer herstellung und sie enthaltende arzneimittel
DE2227846A1 (de)	1973-01-04	Phenoxyessigsaeure-derivate und verfahren zu ihrer herstellung
DE2440378A1 (de)	1976-03-04	Arzneimittel mit antiphlogistischen und analgetischen eigenschaften
DE2341894A1 (de)	1974-03-07	Substituierte 2-phenyl-2,3-dihydrobenzo eckige klammer auf b eckige klammer zu thiophen-1,1-dioxyd-derivate, verfahren zu ihrer herstellung und sie enthaltende arzneimittel
DE2827454A1 (de)	1979-01-25	4-homoisotwistanderivate, verfahren zu ihrer herstellung, verwendung derselben und diese enthaltende arzneimittel