LU82236A1 - 9-aminoalkylfluorenes, leur preparation et leur utilisation therapeutique - Google Patents

9-aminoalkylfluorenes, leur preparation et leur utilisation therapeutique Download PDF

Info

Publication number: LU82236A1
Authority: LU; Luxembourg
Prior art keywords: formula; compound; group; alkyl; isopropylaminopropyl
Prior art date: 1979-03-12

Application number

LU82236A

Other languages

English (en)

French (fr)

Inventor

William Bryant Lacefield

Richard Lee Simon

Original Assignee

Lilly Co Eli

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.)

1979-03-12

Filing date

1980-03-10

Publication date

1980-06-06

1980-03-10 Application filed by Lilly Co Eli filed Critical Lilly Co Eli

1980-06-06 Publication of LU82236A1 publication Critical patent/LU82236A1/fr

Links

238000002360 preparation method Methods 0.000 title claims description 5
230000001225 therapeutic effect Effects 0.000 title 1
150000001875 compounds Chemical class 0.000 claims description 75
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 25
125000000217 alkyl group Chemical group 0.000 claims description 17
238000000034 method Methods 0.000 claims description 17
150000003839 salts Chemical class 0.000 claims description 17
238000011282 treatment Methods 0.000 claims description 14
150000001412 amines Chemical class 0.000 claims description 13
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
125000004093 cyano group Chemical group *C#N 0.000 claims description 6
239000001257 hydrogen Substances 0.000 claims description 6
229910052739 hydrogen Inorganic materials 0.000 claims description 6
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
125000005843 halogen group Chemical group 0.000 claims description 5
UCEWGESNIULAGX-UHFFFAOYSA-N indecainide Chemical compound C1=CC=C2C(CCCNC(C)C)(C(N)=O)C3=CC=CC=C3C2=C1 UCEWGESNIULAGX-UHFFFAOYSA-N 0.000 claims description 5
239000007818 Grignard reagent Substances 0.000 claims description 4
125000004429 atom Chemical group 0.000 claims description 4
150000004795 grignard reagents Chemical class 0.000 claims description 4
239000008194 pharmaceutical composition Substances 0.000 claims description 4
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 3
125000003342 alkenyl group Chemical group 0.000 claims description 3
239000000460 chlorine Substances 0.000 claims description 3
229910052801 chlorine Inorganic materials 0.000 claims description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
229910052794 bromium Inorganic materials 0.000 claims description 2
239000003795 chemical substances by application Substances 0.000 claims description 2
125000001309 chloro group Chemical group Cl* 0.000 claims description 2
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
150000002576 ketones Chemical class 0.000 claims description 2
150000003140 primary amides Chemical class 0.000 claims description 2
125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 1
239000004480 active ingredient Substances 0.000 claims 1
230000002152 alkylating effect Effects 0.000 claims 1
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 1
239000003937 drug carrier Substances 0.000 claims 1
208000019622 heart disease Diseases 0.000 claims 1
230000003301 hydrolyzing effect Effects 0.000 claims 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 42
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 39
-1 2-phenetyl Chemical group 0.000 description 27
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 24
206010003119 arrhythmia Diseases 0.000 description 22
239000011541 reaction mixture Substances 0.000 description 20
239000000243 solution Substances 0.000 description 20
239000002904 solvent Substances 0.000 description 20
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 19
NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 19
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
230000006793 arrhythmia Effects 0.000 description 18
239000000203 mixture Substances 0.000 description 17
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
239000000047 product Substances 0.000 description 15
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
239000002253 acid Substances 0.000 description 13
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 12
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
239000002585 base Substances 0.000 description 11
239000002168 alkylating agent Substances 0.000 description 10
229940100198 alkylating agent Drugs 0.000 description 10
238000006243 chemical reaction Methods 0.000 description 10
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
238000010992 reflux Methods 0.000 description 9
239000007787 solid Substances 0.000 description 9
241000282472 Canis lupus familiaris Species 0.000 description 8
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
238000001704 evaporation Methods 0.000 description 8
230000008020 evaporation Effects 0.000 description 8
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 7
238000005804 alkylation reaction Methods 0.000 description 7
238000004458 analytical method Methods 0.000 description 7
239000003416 antiarrhythmic agent Substances 0.000 description 7
238000012360 testing method Methods 0.000 description 7
CJVMCKCMPQEKPZ-UHFFFAOYSA-N 9h-fluorene-9-carbonitrile Chemical compound C1=CC=C2C(C#N)C3=CC=CC=C3C2=C1 CJVMCKCMPQEKPZ-UHFFFAOYSA-N 0.000 description 6
241001465754 Metazoa Species 0.000 description 6
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
150000007513 acids Chemical class 0.000 description 6
230000029936 alkylation Effects 0.000 description 6
229910052757 nitrogen Inorganic materials 0.000 description 6
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
150000002148 esters Chemical class 0.000 description 5
239000000284 extract Substances 0.000 description 5
238000005984 hydrogenation reaction Methods 0.000 description 5
239000003921 oil Substances 0.000 description 5
235000019198 oils Nutrition 0.000 description 5
239000003960 organic solvent Substances 0.000 description 5
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 5
KVMQBCHLEIGTSV-UHFFFAOYSA-N 9-[3-(propan-2-ylamino)propyl]fluorene-9-carbonitrile Chemical compound C1=CC=C2C(CCCNC(C)C)(C#N)C3=CC=CC=C3C2=C1 KVMQBCHLEIGTSV-UHFFFAOYSA-N 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
239000003054 catalyst Substances 0.000 description 4
238000004821 distillation Methods 0.000 description 4
230000000694 effects Effects 0.000 description 4
YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 description 4
150000002220 fluorenes Chemical class 0.000 description 4
239000007789 gas Substances 0.000 description 4
230000007062 hydrolysis Effects 0.000 description 4
238000006460 hydrolysis reaction Methods 0.000 description 4
238000001802 infusion Methods 0.000 description 4
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 4
238000007911 parenteral administration Methods 0.000 description 4
230000033764 rhythmic process Effects 0.000 description 4
150000003335 secondary amines Chemical class 0.000 description 4
229910000104 sodium hydride Inorganic materials 0.000 description 4
230000009466 transformation Effects 0.000 description 4
GRKYBIILBRZHOA-UHFFFAOYSA-N 9-[3-(propan-2-ylamino)propyl]fluoren-9-ol Chemical compound C1=CC=C2C(CCCNC(C)C)(O)C3=CC=CC=C3C2=C1 GRKYBIILBRZHOA-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 3
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
230000003288 anthiarrhythmic effect Effects 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
239000007810 chemical reaction solvent Substances 0.000 description 3
239000003085 diluting agent Substances 0.000 description 3
238000002474 experimental method Methods 0.000 description 3
239000008103 glucose Substances 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
125000000623 heterocyclic group Chemical group 0.000 description 3
239000005457 ice water Substances 0.000 description 3
239000004615 ingredient Substances 0.000 description 3
239000000543 intermediate Substances 0.000 description 3
238000001990 intravenous administration Methods 0.000 description 3
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical group IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 3
239000011777 magnesium Substances 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
150000002825 nitriles Chemical class 0.000 description 3
125000004433 nitrogen atom Chemical group N* 0.000 description 3
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
150000003858 primary carboxamides Chemical class 0.000 description 3
238000001953 recrystallisation Methods 0.000 description 3
125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 3
239000012312 sodium hydride Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
239000003826 tablet Substances 0.000 description 3
JLEPZAUPTZFVIM-RHIZIOMBSA-N (3s,5s,9r,10s,13r,17r)-3-hydroxy-10,13-dimethyl-17-[(2r)-6-methylheptan-2-yl]-1,2,3,4,5,6,9,11,12,15,16,17-dodecahydrocyclopenta[a]phenanthrene-14-carbaldehyde Chemical compound C1[C@@H](O)CC[C@]2(C)[C@@H](CC[C@@]3([C@@H]([C@H](C)CCCC(C)C)CCC33C=O)C)C3=CC[C@H]21 JLEPZAUPTZFVIM-RHIZIOMBSA-N 0.000 description 2
125000004178 (C1-C4) alkyl group Chemical group 0.000 description 2
125000006040 2-hexenyl group Chemical group 0.000 description 2
125000006024 2-pentenyl group Chemical group 0.000 description 2
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
QPWOANSAQQMAPH-UHFFFAOYSA-N 9-(3-piperidin-1-ylpropyl)fluorene-9-carbonitrile Chemical compound C12=CC=CC=C2C2=CC=CC=C2C1(C#N)CCCN1CCCCC1 QPWOANSAQQMAPH-UHFFFAOYSA-N 0.000 description 2
WUIPMJJARAYJLE-UHFFFAOYSA-N 9-[3-(dimethylamino)propyl]fluorene-9-carbonitrile Chemical compound C1=CC=C2C(CCCN(C)C)(C#N)C3=CC=CC=C3C2=C1 WUIPMJJARAYJLE-UHFFFAOYSA-N 0.000 description 2
PWFLISNWYDWJHX-UHFFFAOYSA-N 9h-fluoren-1-ol Chemical compound C12=CC=CC=C2CC2=C1C=CC=C2O PWFLISNWYDWJHX-UHFFFAOYSA-N 0.000 description 2
ABZPQPREPTZBMO-UHFFFAOYSA-N 9h-fluorene-1-carboxamide Chemical compound C1C2=CC=CC=C2C2=C1C(C(=O)N)=CC=C2 ABZPQPREPTZBMO-UHFFFAOYSA-N 0.000 description 2
LPMXVESGRSUGHW-UHFFFAOYSA-N Acolongiflorosid K Natural products OC1C(O)C(O)C(C)OC1OC1CC2(O)CCC3C4(O)CCC(C=5COC(=O)C=5)C4(C)CC(O)C3C2(CO)C(O)C1 LPMXVESGRSUGHW-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
LPMXVESGRSUGHW-GHYGWZAOSA-N Ouabain Natural products O([C@@H]1[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O1)[C@H]1C[C@@H](O)[C@@]2(CO)[C@@](O)(C1)CC[C@H]1[C@]3(O)[C@@](C)([C@H](C4=CC(=O)OC4)CC3)C[C@@H](O)[C@H]21 LPMXVESGRSUGHW-GHYGWZAOSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
229920002472 Starch Polymers 0.000 description 2
244000166550 Strophanthus gratus Species 0.000 description 2
238000005903 acid hydrolysis reaction Methods 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 2
125000004103 aminoalkyl group Chemical group 0.000 description 2
150000001450 anions Chemical class 0.000 description 2
230000037396 body weight Effects 0.000 description 2
WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 2
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 2
150000003857 carboxamides Chemical class 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
238000009833 condensation Methods 0.000 description 2
230000005494 condensation Effects 0.000 description 2
239000013078 crystal Substances 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
229940079593 drug Drugs 0.000 description 2
239000003814 drug Substances 0.000 description 2
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
238000001914 filtration Methods 0.000 description 2
NXNSCUZKMVYAJQ-UHFFFAOYSA-N hydron;9-[3-(propan-2-ylamino)propyl]fluorene-9-carboxamide;chloride Chemical compound Cl.C1=CC=C2C(CCCNC(C)C)(C(N)=O)C3=CC=CC=C3C2=C1 NXNSCUZKMVYAJQ-UHFFFAOYSA-N 0.000 description 2
229910052740 iodine Inorganic materials 0.000 description 2
JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 2
239000007788 liquid Substances 0.000 description 2
229910052749 magnesium Inorganic materials 0.000 description 2
NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 2
BWLFHTUZEZSUSH-UHFFFAOYSA-N n-benzyl-3-chloro-n-propan-2-ylpropan-1-amine Chemical compound ClCCCN(C(C)C)CC1=CC=CC=C1 BWLFHTUZEZSUSH-UHFFFAOYSA-N 0.000 description 2
150000007524 organic acids Chemical class 0.000 description 2
235000005985 organic acids Nutrition 0.000 description 2
KVNYFPKFSJIPBJ-UHFFFAOYSA-N ortho-diethylbenzene Natural products CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 description 2
LPMXVESGRSUGHW-HBYQJFLCSA-N ouabain Chemical compound O[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1O[C@@H]1C[C@@]2(O)CC[C@H]3[C@@]4(O)CC[C@H](C=5COC(=O)C=5)[C@@]4(C)C[C@@H](O)[C@@H]3[C@@]2(CO)[C@H](O)C1 LPMXVESGRSUGHW-HBYQJFLCSA-N 0.000 description 2
229960003343 ouabain Drugs 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
150000003141 primary amines Chemical class 0.000 description 2
238000011321 prophylaxis Methods 0.000 description 2
150000003242 quaternary ammonium salts Chemical class 0.000 description 2
LOUPRKONTZGTKE-LHHVKLHASA-N quinidine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@H]2[C@@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-LHHVKLHASA-N 0.000 description 2
239000008107 starch Substances 0.000 description 2
235000019698 starch Nutrition 0.000 description 2
239000006188 syrup Substances 0.000 description 2
235000020357 syrup Nutrition 0.000 description 2
150000003512 tertiary amines Chemical class 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 1
VOGQZKPKCZDFBF-UHFFFAOYSA-N 1-(3-chloropropyl)-2,6-dimethylpiperidine Chemical compound CC1CCCC(C)N1CCCCl VOGQZKPKCZDFBF-UHFFFAOYSA-N 0.000 description 1
CEEKMXMGOHQJAL-UHFFFAOYSA-N 1-(3-chloropropyl)-2,6-dimethylpiperidine;hydrochloride Chemical compound Cl.CC1CCCC(C)N1CCCCl CEEKMXMGOHQJAL-UHFFFAOYSA-N 0.000 description 1
XZKFBZOAIGFZSU-UHFFFAOYSA-N 1-bromo-4-methylpentane Chemical compound CC(C)CCCBr XZKFBZOAIGFZSU-UHFFFAOYSA-N 0.000 description 1
WFEOGMWEZOBOAI-UHFFFAOYSA-N 1-but-3-ynylpyrrolidine Chemical compound C#CCCN1CCCC1 WFEOGMWEZOBOAI-UHFFFAOYSA-N 0.000 description 1
ZIKHQMQASDDCGT-UHFFFAOYSA-N 1-chloro-n-(2-methylpropyl)pentan-3-amine Chemical compound ClCCC(CC)NCC(C)C ZIKHQMQASDDCGT-UHFFFAOYSA-N 0.000 description 1
LQSQLFOKTMSBEC-UHFFFAOYSA-N 1-prop-2-ynylpiperidine Chemical compound C#CCN1CCCCC1 LQSQLFOKTMSBEC-UHFFFAOYSA-N 0.000 description 1
SDGKUVSVPIIUCF-UHFFFAOYSA-N 2,6-dimethylpiperidine Chemical compound CC1CCCC(C)N1 SDGKUVSVPIIUCF-UHFFFAOYSA-N 0.000 description 1
GTHLNSMGRHRHEI-UHFFFAOYSA-N 2,7-dimethyl-9-[3-(propan-2-ylamino)propyl]fluoren-9-ol Chemical compound C1=C(C)C=C2C(CCCNC(C)C)(O)C3=CC(C)=CC=C3C2=C1 GTHLNSMGRHRHEI-UHFFFAOYSA-N 0.000 description 1
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 description 1
ZFFBIQMNKOJDJE-UHFFFAOYSA-N 2-bromo-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(Br)C(=O)C1=CC=CC=C1 ZFFBIQMNKOJDJE-UHFFFAOYSA-N 0.000 description 1
125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
HFHYSEXNJLYHIF-UHFFFAOYSA-N 2-methyl-n-prop-2-ynylpropan-2-amine Chemical compound CC(C)(C)NCC#C HFHYSEXNJLYHIF-UHFFFAOYSA-N 0.000 description 1
125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
125000005916 2-methylpentyl group Chemical group 0.000 description 1
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
CRDBTWHALLRFOX-UHFFFAOYSA-N 3-(2,6-dimethylpiperidin-1-yl)propan-1-ol Chemical compound CC1CCCC(C)N1CCCO CRDBTWHALLRFOX-UHFFFAOYSA-N 0.000 description 1
XCTKOSQESKGKMR-UHFFFAOYSA-N 3-bromo-n-propan-2-ylpropan-1-amine Chemical compound CC(C)NCCCBr XCTKOSQESKGKMR-UHFFFAOYSA-N 0.000 description 1
NYYRRBOMNHUCLB-UHFFFAOYSA-N 3-chloro-n,n-dimethylpropan-1-amine Chemical compound CN(C)CCCCl NYYRRBOMNHUCLB-UHFFFAOYSA-N 0.000 description 1
QLHYVFSGYNVMPW-UHFFFAOYSA-N 3-chloro-n-methylpropan-1-amine Chemical compound CNCCCCl QLHYVFSGYNVMPW-UHFFFAOYSA-N 0.000 description 1
125000006041 3-hexenyl group Chemical group 0.000 description 1
RXXCIBALSKQCAE-UHFFFAOYSA-N 3-methylbutoxymethylbenzene Chemical compound CC(C)CCOCC1=CC=CC=C1 RXXCIBALSKQCAE-UHFFFAOYSA-N 0.000 description 1
125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000006051 4-methyl-2-pentenyl group Chemical group 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
NQWUNUJSDRTHGZ-UHFFFAOYSA-N 9-(3-aminopropyl)-n-ethylfluorene-9-carboxamide Chemical compound C1=CC=C2C(C(=O)NCC)(CCCN)C3=CC=CC=C3C2=C1 NQWUNUJSDRTHGZ-UHFFFAOYSA-N 0.000 description 1
NKKSWMLGOGXPEB-UHFFFAOYSA-N 9-(3-aminopropyl)fluorene-9-carbonitrile Chemical compound C1=CC=C2C(CCCN)(C#N)C3=CC=CC=C3C2=C1 NKKSWMLGOGXPEB-UHFFFAOYSA-N 0.000 description 1
NZMHPKUOEWBREH-UHFFFAOYSA-N 9-(3-aminopropyl)fluorene-9-carboxamide Chemical compound C1=CC=C2C(CCCN)(C(N)=O)C3=CC=CC=C3C2=C1 NZMHPKUOEWBREH-UHFFFAOYSA-N 0.000 description 1
JWZYSQOGZKASDL-UHFFFAOYSA-N 9-(3-chloropropyl)fluorene-9-carbonitrile Chemical compound C1=CC=C2C(CCCCl)(C#N)C3=CC=CC=C3C2=C1 JWZYSQOGZKASDL-UHFFFAOYSA-N 0.000 description 1
FASDRUDRUNLBGO-UHFFFAOYSA-N 9-(3-piperidin-1-ylpropyl)fluorene-9-carboxamide Chemical compound C12=CC=CC=C2C2=CC=CC=C2C1(C(=O)N)CCCN1CCCCC1 FASDRUDRUNLBGO-UHFFFAOYSA-N 0.000 description 1
SMPHRERYINLJLI-UHFFFAOYSA-N 9-(4-morpholin-4-ylbutyl)fluorene-9-carboxamide Chemical compound C12=CC=CC=C2C2=CC=CC=C2C1(C(=O)N)CCCCN1CCOCC1 SMPHRERYINLJLI-UHFFFAOYSA-N 0.000 description 1
MWNGRXDBDYMZAN-UHFFFAOYSA-N 9-[3-(2,6-dimethylpiperidin-1-yl)propyl]fluorene-9-carbonitrile Chemical compound CC1CCCC(C)N1CCCC1(C#N)C2=CC=CC=C2C2=CC=CC=C21 MWNGRXDBDYMZAN-UHFFFAOYSA-N 0.000 description 1
BTWAQXXXPALPNK-UHFFFAOYSA-N 9-[3-(2,6-dimethylpiperidin-1-yl)propyl]fluorene-9-carboxamide Chemical compound CC1CCCC(C)N1CCCC1(C(N)=O)C2=CC=CC=C2C2=CC=CC=C21 BTWAQXXXPALPNK-UHFFFAOYSA-N 0.000 description 1
DOSXJBUDYQSJSJ-UHFFFAOYSA-N 9-[3-(3-phenylpropylamino)propyl]fluorene-9-carbonitrile Chemical compound C12=CC=CC=C2C2=CC=CC=C2C1(C#N)CCCNCCCC1=CC=CC=C1 DOSXJBUDYQSJSJ-UHFFFAOYSA-N 0.000 description 1
GQWATHRSNVXVOB-UHFFFAOYSA-N 9-[3-(but-2-enylamino)propyl]fluoren-9-ol Chemical compound C1=CC=C2C(CCCNCC=CC)(O)C3=CC=CC=C3C2=C1 GQWATHRSNVXVOB-UHFFFAOYSA-N 0.000 description 1
GZLVUZIYUVRPMA-UHFFFAOYSA-N 9-[3-(diethylamino)propyl]fluorene-9-carbonitrile Chemical compound C1=CC=C2C(CCCN(CC)CC)(C#N)C3=CC=CC=C3C2=C1 GZLVUZIYUVRPMA-UHFFFAOYSA-N 0.000 description 1
UNZMQFVJQIYOBJ-UHFFFAOYSA-N 9-[3-(diethylamino)propyl]fluorene-9-carboxamide Chemical compound C1=CC=C2C(CCCN(CC)CC)(C(N)=O)C3=CC=CC=C3C2=C1 UNZMQFVJQIYOBJ-UHFFFAOYSA-N 0.000 description 1
RZXWADIYMGFFQR-UHFFFAOYSA-N 9-[3-(dimethylamino)propyl]fluorene-9-carboxamide Chemical compound C1=CC=C2C(CCCN(C)C)(C(N)=O)C3=CC=CC=C3C2=C1 RZXWADIYMGFFQR-UHFFFAOYSA-N 0.000 description 1
YCHBPEUTHBKWTD-UHFFFAOYSA-N 9-[3-(hex-3-enylamino)propyl]fluorene-9-carbonitrile Chemical compound C1=CC=C2C(CCCNCCC=CCC)(C#N)C3=CC=CC=C3C2=C1 YCHBPEUTHBKWTD-UHFFFAOYSA-N 0.000 description 1
UZGBDBFDLGSSKH-UHFFFAOYSA-N 9-[3-(hexylamino)propyl]fluoren-9-ol Chemical compound C1=CC=C2C(CCCNCCCCCC)(O)C3=CC=CC=C3C2=C1 UZGBDBFDLGSSKH-UHFFFAOYSA-N 0.000 description 1
XAYSIPZPDWYCBN-UHFFFAOYSA-N 9-[3-(pentylamino)propyl]fluorene-9-carboxamide Chemical group C1=CC=C2C(CCCNCCCCC)(C(N)=O)C3=CC=CC=C3C2=C1 XAYSIPZPDWYCBN-UHFFFAOYSA-N 0.000 description 1
ICSWQSCPUKKCGQ-UHFFFAOYSA-N 9-[3-(propan-2-ylamino)prop-1-ynyl]fluoren-9-ol Chemical compound C1=CC=C2C(C#CCNC(C)C)(O)C3=CC=CC=C3C2=C1 ICSWQSCPUKKCGQ-UHFFFAOYSA-N 0.000 description 1
AEFZMCKKGJQBBL-UHFFFAOYSA-N 9-[3-(tert-butylamino)propyl]fluoren-9-ol;hydrobromide Chemical compound Br.C1=CC=C2C(CCCNC(C)(C)C)(O)C3=CC=CC=C3C2=C1 AEFZMCKKGJQBBL-UHFFFAOYSA-N 0.000 description 1
UXBACLCXXGGTEP-UHFFFAOYSA-N 9-[3-[di(propan-2-yl)amino]propyl]-n,n-di(propan-2-yl)fluorene-9-carboxamide Chemical group C1=CC=C2C(CCCN(C(C)C)C(C)C)(C(=O)N(C(C)C)C(C)C)C3=CC=CC=C3C2=C1 UXBACLCXXGGTEP-UHFFFAOYSA-N 0.000 description 1
WOPWXLIGRGPPSP-UHFFFAOYSA-N 9-[3-[di(propan-2-yl)amino]propyl]fluoren-9-ol Chemical compound C1=CC=C2C(CCCN(C(C)C)C(C)C)(O)C3=CC=CC=C3C2=C1 WOPWXLIGRGPPSP-UHFFFAOYSA-N 0.000 description 1
FZHFFKJONQYCNO-UHFFFAOYSA-N 9-[4-(2-phenylethylamino)butyl]fluoren-9-ol Chemical compound C12=CC=CC=C2C2=CC=CC=C2C1(O)CCCCNCCC1=CC=CC=C1 FZHFFKJONQYCNO-UHFFFAOYSA-N 0.000 description 1
GYOXDGSLNWONMA-UHFFFAOYSA-N 9-[4-(benzylamino)butyl]-n,n-dibutylfluorene-9-carboxamide Chemical compound C12=CC=CC=C2C2=CC=CC=C2C1(C(=O)N(CCCC)CCCC)CCCCNCC1=CC=CC=C1 GYOXDGSLNWONMA-UHFFFAOYSA-N 0.000 description 1
GKOCNZFDOOURBJ-UHFFFAOYSA-N 9-[4-(diethylamino)butyl]fluorene-9-carbonitrile Chemical compound C1=CC=C2C(CCCCN(CC)CC)(C#N)C3=CC=CC=C3C2=C1 GKOCNZFDOOURBJ-UHFFFAOYSA-N 0.000 description 1
IONBRWYIPOJNRR-UHFFFAOYSA-N 9-[4-(hex-2-enylamino)butyl]fluorene-9-carboxamide Chemical compound C1=CC=C2C(CCCCNCC=CCCC)(C(N)=O)C3=CC=CC=C3C2=C1 IONBRWYIPOJNRR-UHFFFAOYSA-N 0.000 description 1
HJMRMVNYQSDSJA-UHFFFAOYSA-N 9-[4-(propan-2-ylamino)butyl]fluoren-9-ol Chemical compound C1=CC=C2C(CCCCNC(C)C)(O)C3=CC=CC=C3C2=C1 HJMRMVNYQSDSJA-UHFFFAOYSA-N 0.000 description 1
HTPXFGUCAUTOEL-UHFFFAOYSA-N 9h-fluorene-1-carboxylic acid Chemical compound C1C2=CC=CC=C2C2=C1C(C(=O)O)=CC=C2 HTPXFGUCAUTOEL-UHFFFAOYSA-N 0.000 description 1
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 1
229910015900 BF3 Inorganic materials 0.000 description 1
ZOXJGFHDIHLPTG-BJUDXGSMSA-N Boron-10 Chemical compound [10B] ZOXJGFHDIHLPTG-BJUDXGSMSA-N 0.000 description 1
COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
CAQWNKXTMBFBGI-UHFFFAOYSA-N C.[Na] Chemical compound C.[Na] CAQWNKXTMBFBGI-UHFFFAOYSA-N 0.000 description 1
125000004648 C2-C8 alkenyl group Chemical group 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
208000024172 Cardiovascular disease Diseases 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
NNLATLBKJTZJDP-UHFFFAOYSA-N ClCCCC1(C2=CC=CC=C2C=2C=CC=CC12)C#N.Cl Chemical compound ClCCCC1(C2=CC=CC=C2C=2C=CC=CC12)C#N.Cl NNLATLBKJTZJDP-UHFFFAOYSA-N 0.000 description 1
240000001879 Digitalis lutea Species 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
238000003747 Grignard reaction Methods 0.000 description 1
MFESCIUQSIBMSM-UHFFFAOYSA-N I-BCP Chemical compound ClCCCBr MFESCIUQSIBMSM-UHFFFAOYSA-N 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
NNJVILVZKWQKPM-UHFFFAOYSA-N Lidocaine Chemical compound CCN(CC)CC(=O)NC1=C(C)C=CC=C1C NNJVILVZKWQKPM-UHFFFAOYSA-N 0.000 description 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
238000010934 O-alkylation reaction Methods 0.000 description 1
240000007594 Oryza sativa Species 0.000 description 1
235000007164 Oryza sativa Nutrition 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
DMDHQZQWVAXSDF-UHFFFAOYSA-N S(=O)(=O)(O)O.C(C)(C)NCCCC1(C2=CC=CC=C2C=2C=CC=CC12)C#N Chemical compound S(=O)(=O)(O)O.C(C)(C)NCCCC1(C2=CC=CC=C2C=2C=CC=CC12)C#N DMDHQZQWVAXSDF-UHFFFAOYSA-N 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
229930006000 Sucrose Natural products 0.000 description 1
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
RDFKRSLUNOBGIK-UHFFFAOYSA-M [Cl-].C(C)(C)N(CCC[Mg+])C(C)C Chemical compound [Cl-].C(C)(C)N(CCC[Mg+])C(C)C RDFKRSLUNOBGIK-UHFFFAOYSA-M 0.000 description 1
230000002159 abnormal effect Effects 0.000 description 1
OAWYDLKHZQNWBN-UHFFFAOYSA-N acetic acid;9-[3-(propan-2-ylamino)propyl]fluorene-9-carboxamide Chemical compound CC(O)=O.C1=CC=C2C(CCCNC(C)C)(C(N)=O)C3=CC=CC=C3C2=C1 OAWYDLKHZQNWBN-UHFFFAOYSA-N 0.000 description 1
230000004913 activation Effects 0.000 description 1
229910000102 alkali metal hydride Inorganic materials 0.000 description 1
150000008046 alkali metal hydrides Chemical class 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
125000005907 alkyl ester group Chemical group 0.000 description 1
125000002947 alkylene group Chemical group 0.000 description 1
238000005905 alkynylation reaction Methods 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
239000000010 aprotic solvent Substances 0.000 description 1
239000011260 aqueous acid Substances 0.000 description 1
230000002763 arrhythmic effect Effects 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 description 1
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
238000004166 bioassay Methods 0.000 description 1
230000004071 biological effect Effects 0.000 description 1
RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
230000005587 bubbling Effects 0.000 description 1
125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
KMGBZBJJOKUPIA-UHFFFAOYSA-N butyl iodide Chemical compound CCCCI KMGBZBJJOKUPIA-UHFFFAOYSA-N 0.000 description 1
239000002775 capsule Substances 0.000 description 1
235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
239000001768 carboxy methyl cellulose Substances 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
239000008112 carboxymethyl-cellulose Substances 0.000 description 1
210000000748 cardiovascular system Anatomy 0.000 description 1
239000000969 carrier Substances 0.000 description 1
NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 description 1
LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 description 1
229940125773 compound 10 Drugs 0.000 description 1
229940125782 compound 2 Drugs 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000002285 corn oil Substances 0.000 description 1
235000005687 corn oil Nutrition 0.000 description 1
230000034994 death Effects 0.000 description 1
231100000517 death Toxicity 0.000 description 1
PBGGNZZGJIKBMJ-UHFFFAOYSA-N di(propan-2-yl)azanide Chemical compound CC(C)[N-]C(C)C PBGGNZZGJIKBMJ-UHFFFAOYSA-N 0.000 description 1
238000010586 diagram Methods 0.000 description 1
238000007865 diluting Methods 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
238000001035 drying Methods 0.000 description 1
125000004185 ester group Chemical group 0.000 description 1
235000019441 ethanol Nutrition 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
235000013312 flour Nutrition 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
239000012458 free base Substances 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
210000002837 heart atrium Anatomy 0.000 description 1
125000005842 heteroatom Chemical group 0.000 description 1
238000007327 hydrogenolysis reaction Methods 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
238000007918 intramuscular administration Methods 0.000 description 1
238000007912 intraperitoneal administration Methods 0.000 description 1
238000010253 intravenous injection Methods 0.000 description 1
239000011630 iodine Substances 0.000 description 1
HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical group CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
238000002955 isolation Methods 0.000 description 1
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical class C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
239000008101 lactose Substances 0.000 description 1
229960004194 lidocaine Drugs 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
AFRJJFRNGGLMDW-UHFFFAOYSA-N lithium amide Chemical compound [Li+].[NH2-] AFRJJFRNGGLMDW-UHFFFAOYSA-N 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
238000011418 maintenance treatment Methods 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
239000011976 maleic acid Substances 0.000 description 1
150000002689 maleic acids Chemical class 0.000 description 1
229940102396 methyl bromide Drugs 0.000 description 1
DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
239000011707 mineral Substances 0.000 description 1
238000002156 mixing Methods 0.000 description 1
125000000896 monocarboxylic acid group Chemical group 0.000 description 1
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
XKRQLFAFMZSNJH-UHFFFAOYSA-N n,n-diethyl-3-iodopropan-1-amine Chemical compound CCN(CC)CCCI XKRQLFAFMZSNJH-UHFFFAOYSA-N 0.000 description 1
CGSBVEHGUHCRCB-UHFFFAOYSA-N n,n-diethylbut-3-yn-1-amine Chemical compound CCN(CC)CCC#C CGSBVEHGUHCRCB-UHFFFAOYSA-N 0.000 description 1
CZOOVKHMGMYWGD-UHFFFAOYSA-N n-(3-bromopropyl)-n-hexylhexan-1-amine Chemical compound CCCCCCN(CCCBr)CCCCCC CZOOVKHMGMYWGD-UHFFFAOYSA-N 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
PUHYNZVAXFZYFB-UHFFFAOYSA-N n-methyl-9-[3-(propan-2-ylamino)propyl]fluorene-9-carboxamide Chemical compound C1=CC=C2C(C(=O)NC)(CCCNC(C)C)C3=CC=CC=C3C2=C1 PUHYNZVAXFZYFB-UHFFFAOYSA-N 0.000 description 1
HQFYIDOMCULPIW-UHFFFAOYSA-N n-methylprop-2-yn-1-amine Chemical compound CNCC#C HQFYIDOMCULPIW-UHFFFAOYSA-N 0.000 description 1
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
BQMKURIMSKNDLR-UHFFFAOYSA-N n-prop-2-ynylpropan-2-amine Chemical compound CC(C)NCC#C BQMKURIMSKNDLR-UHFFFAOYSA-N 0.000 description 1
WIIRJYRINSFNSN-UHFFFAOYSA-N n-propan-2-yl-9-[3-(propan-2-ylamino)propyl]fluorene-9-carboxamide;hydrochloride Chemical compound Cl.C1=CC=C2C(CCCNC(C)C)(C(=O)NC(C)C)C3=CC=CC=C3C2=C1 WIIRJYRINSFNSN-UHFFFAOYSA-N 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
PVWOIHVRPOBWPI-UHFFFAOYSA-N n-propyl iodide Chemical compound CCCI PVWOIHVRPOBWPI-UHFFFAOYSA-N 0.000 description 1
239000002547 new drug Substances 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
239000007935 oral tablet Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
AHWALFGBDFAJAI-UHFFFAOYSA-N phenyl carbonochloridate Chemical compound ClC(=O)OC1=CC=CC=C1 AHWALFGBDFAJAI-UHFFFAOYSA-N 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
229910000105 potassium hydride Inorganic materials 0.000 description 1
NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
REQCZEXYDRLIBE-UHFFFAOYSA-N procainamide Chemical compound CCN(CC)CCNC(=O)C1=CC=C(N)C=C1 REQCZEXYDRLIBE-UHFFFAOYSA-N 0.000 description 1
229960000244 procainamide Drugs 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
229960001404 quinidine Drugs 0.000 description 1
235000009566 rice Nutrition 0.000 description 1
210000002966 serum Anatomy 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
RGHFKWPGWBFQLN-UHFFFAOYSA-M sodium;5,5-diethylpyrimidin-3-ide-2,4,6-trione Chemical compound [Na+].CCC1(CC)C([O-])=NC(=O)NC1=O RGHFKWPGWBFQLN-UHFFFAOYSA-M 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
238000010254 subcutaneous injection Methods 0.000 description 1
239000005720 sucrose Substances 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
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
230000002936 tranquilizing effect 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
210000003462 vein Anatomy 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/33—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic 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
- C07D295/096—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 with the ring nitrogen atoms and the oxygen or sulfur atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
- A—HUMAN NECESSITIES
- A41—WEARING APPAREL
- A41D—OUTERWEAR; PROTECTIVE GARMENTS; ACCESSORIES
- A41D31/00—Materials specially adapted for outerwear
- A41D31/04—Materials specially adapted for outerwear characterised by special function or use
- A41D31/10—Impermeable to liquids, e.g. waterproof; Liquid-repellent
- A41D31/102—Waterproof and breathable
- A—HUMAN NECESSITIES
- A41—WEARING APPAREL
- A41D—OUTERWEAR; PROTECTIVE GARMENTS; ACCESSORIES
- A41D31/00—Materials specially adapted for outerwear
- A41D31/04—Materials specially adapted for outerwear characterised by special function or use
- A41D31/18—Elastic
- A41D31/185—Elastic using layered materials
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/06—Antiarrhythmics
- 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
- C07D295/14—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 carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D295/155—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 carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic 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
- C07C2603/06—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

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Life Sciences & Earth Sciences (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Chemical Kinetics & Catalysis (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmacology & Pharmacy (AREA)
Medicinal Chemistry (AREA)
General Chemical & Material Sciences (AREA)
Heart & Thoracic Surgery (AREA)
Cardiology (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Textile Engineering (AREA)
Epidemiology (AREA)
Birds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Hydrogenated Pyridines (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

LU82236A 1979-03-12 1980-03-10 9-aminoalkylfluorenes, leur preparation et leur utilisation therapeutique LU82236A1 (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US1953379A	1979-03-12	1979-03-12
US1953379		1979-03-12

Publications (1)

Publication Number	Publication Date
LU82236A1 true LU82236A1 (fr)	1980-06-06

Family

ID=21793707

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
LU82236A LU82236A1 (fr)	1979-03-12	1980-03-10	9-aminoalkylfluorenes, leur preparation et leur utilisation therapeutique

Country Status (40)

Country	Link
US (1)	US4277495A (de)
EP (1)	EP0018076B1 (de)
JP (1)	JPS55124743A (de)
KR (2)	KR840000279B1 (de)
AR (6)	AR228851A1 (de)
AT (4)	AT370407B (de)
AU (1)	AU527992B2 (de)
BE (1)	BE882166A (de)
CA (1)	CA1136624A (de)
CH (1)	CH643234A5 (de)
CS (4)	CS214696B2 (de)
CY (1)	CY1345A (de)
DD (1)	DD149511A5 (de)
DE (1)	DE3064872D1 (de)
DK (1)	DK158658C (de)
EG (1)	EG14592A (de)
ES (5)	ES489470A0 (de)
FI (3)	FI67211C (de)
FR (2)	FR2460287A1 (de)
GB (1)	GB2046257B (de)
GR (1)	GR68035B (de)
GT (1)	GT198062477A (de)
HK (1)	HK101086A (de)
HU (1)	HU179837B (de)
IE (1)	IE49553B1 (de)
IL (1)	IL59558A (de)
IT (1)	IT1140772B (de)
LU (1)	LU82236A1 (de)
MA (1)	MA18763A1 (de)
MY (1)	MY8700080A (de)
NZ (1)	NZ193078A (de)
OA (1)	OA06486A (de)
PH (1)	PH15594A (de)
PL (1)	PL122643B1 (de)
PT (1)	PT70927A (de)
RO (2)	RO79822A (de)
SG (1)	SG72286G (de)
SU (2)	SU1022656A3 (de)
YU (1)	YU65680A (de)
ZA (1)	ZA801422B (de)

Families Citing this family (14)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4212337A (en) *	1978-03-31	1980-07-15	Union Carbide Corporation	Closure fastening device
US4452745A (en) *	1981-02-06	1984-06-05	Eli Lilly And Company	9-Aminoalkylfluorenes
US4484352A (en) *	1983-02-07	1984-11-20	Katzin Lawrence F	Reclosable plastic bag
US4552982A (en) *	1983-08-01	1985-11-12	Eli Lilly And Company	Synthesis of 9-carbamoyl-9-(3-aminopropyl)fluorenes
US4508735A (en) *	1983-09-21	1985-04-02	Eli Lilly And Company	Anti-arrhythmic N-alkanoylaminoalkyl fluorenes
US4486592A (en) *	1983-10-19	1984-12-04	Eli Lilly And Company	9-Carbamoylfluorene derivatives
US4585894A (en) *	1983-10-19	1986-04-29	Eli Lilly And Company	Process for producing 9-carbamoyl fluorene derivatives
IL73261A (en) *	1983-10-19	1988-03-31	Lilly Co Eli	Process for producing 9-carbamoyl-9-aminoalkyl fluorene derivatives,and certain intermediates thereof
DE3444837A1 (de) *	1984-12-08	1986-06-12	Basf Ag, 6700 Ludwigshafen	10,11-dihydro-5h-dibenzo(a,d)cycloheptadien- derivate, ihre herstellung und verwendung
GB9304189D0 (en) *	1993-03-02	1993-04-21	Sturmey Archer Ltd	Epicyclic change speed gear hubs
US5739135A (en) *	1993-09-03	1998-04-14	Bristol-Myers Squibb Company	Inhibitors of microsomal triglyceride transfer protein and method
US5631203A (en) *	1995-05-04	1997-05-20	Phillips Petroleum Company	Metallocene compounds and preparation thereof containing terminal alkynes
NZ330216A (en) *	1996-01-16	2000-09-29	Bristol Myers Squibb Co	Conformationally restricted aromatic inhibitors of microsomal triglyceride transfer protein and use in treatment of atherosclerosis
US5760246A (en)	1996-12-17	1998-06-02	Biller; Scott A.	Conformationally restricted aromatic inhibitors of microsomal triglyceride transfer protein and method

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB736372A (en) *	1953-05-06	1955-09-07	Miles Lab	Fluorene derivatives
FR1345419A (fr) *	1962-12-21	1963-12-06	Boehringer & Soehne Gmbh	Procédé pour la préparation de dérivés basiques du fluorène et des sels de ces dérivés
NL287095A (de)	1962-12-21	1965-02-25
DE1203253B (de) *	1963-02-09	1965-10-21	Boehringer & Soehne Gmbh	Verfahren zur Herstellung basischer Fluorenderivate und ihrer Salze
FR1482727A (fr) *	1965-06-10	1967-05-26	Upjohn Co	9-(2-amino-1-méthyléthyl) fluoren-9-ols et leur procédé de fabrication
GB1211459A (en) *	1967-05-10	1970-11-04	Abbott Lab	Hydroxy amines
US3660485A (en) *	1970-10-05	1972-05-02	Searle & Co	Fluorene-9-carboxylic acid hydrazides
US3843657A (en) *	1972-12-08	1974-10-22	Searle & Co	9-dialkylamin oalkyl-n-substituted fluorene-9-carboxamides

1980
- 1980-03-04 MA MA18961A patent/MA18763A1/fr unknown
- 1980-03-09 IL IL59558A patent/IL59558A/xx not_active IP Right Cessation
- 1980-03-10 PH PH23742A patent/PH15594A/en unknown
- 1980-03-10 LU LU82236A patent/LU82236A1/fr unknown
- 1980-03-10 CH CH186780A patent/CH643234A5/fr not_active IP Right Cessation
- 1980-03-10 GR GR61386A patent/GR68035B/el unknown
- 1980-03-10 RO RO80100428A patent/RO79822A/ro unknown
- 1980-03-10 HU HU8080562A patent/HU179837B/hu not_active IP Right Cessation
- 1980-03-10 FR FR8005310A patent/FR2460287A1/fr active Granted
- 1980-03-10 CA CA000347366A patent/CA1136624A/en not_active Expired
- 1980-03-10 AU AU56301/80A patent/AU527992B2/en not_active Ceased
- 1980-03-10 YU YU00656/80A patent/YU65680A/xx unknown
- 1980-03-10 NZ NZ193078A patent/NZ193078A/xx unknown
- 1980-03-10 PT PT70927A patent/PT70927A/pt not_active IP Right Cessation
- 1980-03-11 PL PL1980222600A patent/PL122643B1/pl unknown
- 1980-03-11 FI FI800735A patent/FI67211C/fi not_active IP Right Cessation
- 1980-03-11 JP JP3256780A patent/JPS55124743A/ja active Granted
- 1980-03-11 BE BE1/9746A patent/BE882166A/fr not_active IP Right Cessation
- 1980-03-11 CS CS801664A patent/CS214696B2/cs unknown
- 1980-03-11 DK DK103380A patent/DK158658C/da not_active IP Right Cessation
- 1980-03-11 CS CS807588A patent/CS214699B2/cs unknown
- 1980-03-11 AT AT0134480A patent/AT370407B/de not_active IP Right Cessation
- 1980-03-11 IT IT20502/80A patent/IT1140772B/it active
- 1980-03-11 CS CS807589A patent/CS214700B2/cs unknown
- 1980-03-11 CY CY1345A patent/CY1345A/xx unknown
- 1980-03-11 GT GT198062477A patent/GT198062477A/es unknown
- 1980-03-11 ZA ZA00801422A patent/ZA801422B/xx unknown
- 1980-03-11 GB GB8008171A patent/GB2046257B/en not_active Expired
- 1980-03-11 IE IE494/80A patent/IE49553B1/en not_active IP Right Cessation
- 1980-03-11 EG EG80144A patent/EG14592A/xx active
- 1980-03-11 DE DE8080300745T patent/DE3064872D1/de not_active Expired
- 1980-03-11 EP EP80300745A patent/EP0018076B1/de not_active Expired
- 1980-03-11 CS CS807587A patent/CS214698B2/cs unknown
- 1980-03-12 DD DD80219616A patent/DD149511A5/de not_active IP Right Cessation
- 1980-03-12 ES ES489470A patent/ES489470A0/es active Granted
- 1980-03-12 OA OA57051A patent/OA06486A/xx unknown
- 1980-03-12 AR AR280279A patent/AR228851A1/es active
- 1980-03-12 KR KR1019800001022A patent/KR840000279B1/ko not_active Expired
- 1980-04-17 US US06/141,228 patent/US4277495A/en not_active Expired - Lifetime
- 1980-09-01 FR FR8018884A patent/FR2457278A1/fr active Granted
- 1980-11-28 ES ES497300A patent/ES497300A0/es active Granted
- 1980-11-28 ES ES497302A patent/ES8201947A1/es not_active Expired
- 1980-11-28 ES ES497303A patent/ES8201943A1/es not_active Expired
- 1980-11-28 ES ES497301A patent/ES497301A0/es active Granted
1981
- 1981-01-14 SU SU813229056A patent/SU1022656A3/ru active
- 1981-01-15 SU SU813229055A patent/SU1015820A3/ru active
- 1981-03-12 AT AT0114081A patent/AT368130B/de not_active IP Right Cessation
- 1981-03-12 AT AT0114181A patent/AT368131B/de not_active IP Right Cessation
- 1981-03-12 AT AT0113981A patent/AT368125B/de not_active IP Right Cessation
- 1981-06-22 AR AR285808A patent/AR229402A1/es active
- 1981-06-22 AR AR285804A patent/AR225526A1/es active
- 1981-06-22 AR AR285807A patent/AR230983A1/es active
- 1981-06-22 AR AR285805A patent/AR227318A1/es active
- 1981-06-22 AR AR285806A patent/AR228059A1/es active
1983
- 1983-03-10 RO RO83108965A patent/RO85074A/ro unknown
- 1983-10-07 KR KR1019830004760A patent/KR840001836B1/ko not_active Expired
1984
- 1984-03-07 FI FI840921A patent/FI70006C/fi not_active IP Right Cessation
- 1984-03-07 FI FI840920A patent/FI69299C/fi not_active IP Right Cessation
1986
- 1986-09-06 SG SG722/86A patent/SG72286G/en unknown
- 1986-12-24 HK HK1010/86A patent/HK101086A/xx unknown
1987
- 1987-12-30 MY MY80/87A patent/MY8700080A/xx unknown

Also Published As

Publication number	Publication date
FR2460287A1 (fr)	1981-01-23
FI67211C (fi)	1985-02-11
AT370407B (de)	1983-03-25
ES497303A0 (es)	1982-01-01
SU1022656A3 (ru)	1983-06-07
FR2460287B1 (de)	1983-03-11
DD149511A5 (de)	1981-07-15
IL59558A0 (en)	1980-06-30
CS214699B2 (en)	1982-05-28
ATA134480A (de)	1982-08-15
ATA113981A (de)	1982-01-15
FI800735A7 (fi)	1980-09-13
RO85074A (ro)	1984-08-17
IT1140772B (it)	1986-10-10
DE3064872D1 (en)	1983-10-27
FI840920L (fi)	1984-03-07
AR228851A1 (es)	1983-04-29
FI840921L (fi)	1984-03-07
FI67211B (fi)	1984-10-31
AR230983A1 (es)	1984-08-31
IL59558A (en)	1984-05-31
KR840000279B1 (ko)	1984-03-13
JPS6314702B2 (de)	1988-04-01
AR227318A1 (es)	1982-10-15
KR830001860A (ko)	1983-05-19
SU1015820A3 (ru)	1983-04-30
ES497302A0 (es)	1982-01-01
AT368125B (de)	1982-09-10
EP0018076B1 (de)	1983-09-21
CS214700B2 (en)	1982-05-28
AU5630180A (en)	1980-09-18
ATA114081A (de)	1982-01-15
ES8201945A1 (es)	1982-01-01
KR840001836B1 (ko)	1984-10-22
ES8201946A1 (es)	1982-01-01
AT368131B (de)	1982-09-10
ATA114181A (de)	1982-01-15
CY1345A (en)	1987-01-16
MA18763A1 (fr)	1980-10-01
AR228059A1 (es)	1983-01-14
ES8104186A1 (es)	1981-04-16
AR225526A1 (es)	1982-03-31
GT198062477A (es)	1981-09-02
GB2046257B (en)	1983-10-19
FI69299B (fi)	1985-09-30
GR68035B (de)	1981-10-27
FI70006C (fi)	1986-09-12
BE882166A (fr)	1980-09-11
DK158658C (da)	1990-12-31
DK158658B (da)	1990-07-02
IE49553B1 (en)	1985-10-30
CA1136624A (en)	1982-11-30
GB2046257A (en)	1980-11-12
PL122643B1 (en)	1982-08-31
AU527992B2 (en)	1983-03-31
JPS55124743A (en)	1980-09-26
IT8020502A0 (it)	1980-03-11
NZ193078A (en)	1981-11-19
ES8201947A1 (es)	1982-01-01
MY8700080A (en)	1987-12-31
CS214696B2 (en)	1982-05-28
RO79822A (ro)	1983-02-01
ES8201943A1 (es)	1982-01-01
DK103380A (da)	1980-09-13
AR229402A1 (es)	1983-08-15
AT368130B (de)	1982-09-10
EG14592A (en)	1985-03-31
FR2457278A1 (fr)	1980-12-19
FR2457278B1 (de)	1984-06-29
SG72286G (en)	1987-03-27
FI69299C (fi)	1986-01-10
PH15594A (en)	1983-02-28
FI840921A0 (fi)	1984-03-07
OA06486A (fr)	1981-07-31
CS214698B2 (en)	1982-05-28
PL222600A1 (de)	1980-12-15
FI70006B (fi)	1986-01-31
ES497300A0 (es)	1982-01-01
EP0018076A1 (de)	1980-10-29
HU179837B (en)	1982-12-28
ES497301A0 (es)	1982-01-01
FI840920A0 (fi)	1984-03-07
CH643234A5 (fr)	1984-05-30
PT70927A (en)	1980-04-01
ES489470A0 (es)	1981-04-16
US4277495A (en)	1981-07-07
YU65680A (en)	1983-02-28
ZA801422B (en)	1981-10-28
IE800494L (en)	1980-09-12
HK101086A (en)	1987-01-02

Publication	Publication Date	Title
LU82387A1 (fr)	1980-07-31	Esters d'acyl-carnitines,leur procede de preparation et compositions pharmaceutiques contenant ces esters
EP0745586A1 (de)	1996-12-04	Aryl(alkyl)propylamide, Verfahren zu ihrer Herstellung und pharmazeutische Zusammensetzungen, die sie enthalten
EP0506532A1 (de)	1992-09-30	Indolderivate, Verfahren zu deren Herstellung und diese enthaltende Arzneimittel
LU82236A1 (fr)	1980-06-06	9-aminoalkylfluorenes, leur preparation et leur utilisation therapeutique
EP0373998A1 (de)	1990-06-20	Propenonoximether, Verfahren zu dessen Herstellung sowie diese enthaltende Arzneinmittel
EP0125195B1 (de)	1987-09-30	4'-Flavonkarbonsäuren, Verfahren zu deren Herstellung und ihre therapeutische Verwendung
EP0062596B1 (de)	1985-07-03	Derivate von 4-Aminoäthoxy-5-isopropyl-2-methylphenolen, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel
EP0077427B1 (de)	1985-05-22	Piperidin-Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel
EP0737670A1 (de)	1996-10-16	Tricyclische Amidverbindungen, Verfahren zu deren Herstellung und sie enthaltende pharmazeutische Zusammensetzungen
EP0745584A1 (de)	1996-12-04	Arylalkyl(thio)carboxamidverbindungen mit Affinität für Melatoninrezeptoren, Verfahren zu ihrer Herstellung und sie enthaltende pharmazeutische Zusammensetzungen
EP0063084B1 (de)	1984-09-12	Phenethanolamin-Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel
US4658061A (en)	1987-04-14	9-aminoalkylfluorenes
EP0138714B1 (de)	1987-05-20	1-(Acetylaminophenyl)-2-Amino-Propanon-Derivate, deren therapeutische Verwendung und Verfahren zu deren Herstellung
CH622795A5 (de)	1981-04-30
EP0201400A1 (de)	1986-12-17	4-Phenylpropylindolderivate und ihre Salze, Verfahren zur Herstellung, deren Anwendung als Heilmittel und sie enthaltende pharmazeutische Zusammensetzungen
EP0002401B1 (de)	1980-12-10	Naphtalen-Derivate, Verfahren zu deren Herstellung und deren Verwendung in der Therapeutik
EP0275762B1 (de)	1993-11-18	Indol-Carboxamid-Derivate und ihre Salze, Verfahren und Zwischenprodukte zur Herstellung, Anwendung als Heilmittel und Zusammenstellungen, die sie enthalten
CH658786A5 (fr)	1986-12-15	Medicaments qui contiennent d'alpha-(n-pyrrolyl)-acides ou de leurs sels ou esters.
EP0709371B1 (de)	1998-05-06	O-Arylmethyl-N-(thio)acyl-hydroxylamine als Liganden des Melatoninrezeptors, Verfahren zu ihrer Herstellung und sie enthaltende pharmazeutische Zusammensetzungen
LU82237A1 (fr)	1980-06-06	(1,1-biphenyl-2-yl)-propyl- et butylamines, leur preparatin et leur utilisation therapeutique
CH620678A5 (en)	1980-12-15	Process for the preparation of a derivative of piperidine
BE897281A (fr)	1983-11-03	Le 2 (hexahydroazepine)-n-(2,6-dimethylphenyle)-acetamide son derive chlorhydrate, procede pour leur obtention et compositions pharmaceutique les contenant
CH618970A5 (en)	1980-08-29	Process for the preparation of 4-amido-trans-decahydroquinoline derivatives
BE822193A (fr)	1975-05-14	Nouveaux composes aromatiques amines
FR2610931A1 (fr)	1988-08-19	Application a titre de medicaments de derives de la dihydroquinidine, nouveaux derives et procede de preparation