ES294340A1 - Procedimiento para la preparaciën de nuevos derivados azepinicos - Google Patents

Procedimiento para la preparaciën de nuevos derivados azepinicos

Info

Publication number: ES294340A1
Authority: ES; Spain
Prior art keywords: azepine; dibenz; methyl; acetyl; chloro
Prior art date: 1962-12-04
Legal status (The legal status 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 status listed.): Expired

Application number

ES0294340A

Other languages

English (en)

Spanish (es)

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Novartis AG

Original Assignee

JR Geigy AG

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

1962-12-04

Filing date

1963-12-03

Publication date

1964-06-01

1963-12-03 Application filed by JR Geigy AG filed Critical JR Geigy AG

1964-06-01 Publication of ES294340A1 publication Critical patent/ES294340A1/es

Status Expired legal-status Critical Current

Links

150000001538 azepines Chemical class 0.000 title abstract 3
239000000203 mixture Substances 0.000 title 1
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 abstract 12
-1 alkanoyl radical Chemical class 0.000 abstract 6
ROSDSFDQCJNGOL-UHFFFAOYSA-N protonated dimethyl amine Natural products CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 abstract 5
150000001875 compounds Chemical class 0.000 abstract 4
239000001257 hydrogen Substances 0.000 abstract 4
229910052739 hydrogen Inorganic materials 0.000 abstract 4
230000007062 hydrolysis Effects 0.000 abstract 4
238000006460 hydrolysis reaction Methods 0.000 abstract 4
235000011118 potassium hydroxide Nutrition 0.000 abstract 4
150000003839 salts Chemical class 0.000 abstract 4
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 abstract 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 abstract 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 abstract 2
239000002253 acid Substances 0.000 abstract 2
125000004432 carbon atom Chemical group C* 0.000 abstract 2
125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
125000004433 nitrogen atom Chemical group N* 0.000 abstract 2
150000007524 organic acids Chemical class 0.000 abstract 2
150000003254 radicals Chemical class 0.000 abstract 2
239000000932 sedative agent Substances 0.000 abstract 2
KEVXBVBTHBDMBY-UHFFFAOYSA-N (6-methyl-11H-benzo[b][1]benzazepin-4-yl)methanamine Chemical compound CC1=CC2=C(NC3=C1C=CC=C3)C=CC=C2CN KEVXBVBTHBDMBY-UHFFFAOYSA-N 0.000 abstract 1
JMGCRTKWZXSNEW-UHFFFAOYSA-N 1-(11H-benzo[b][1]benzazepin-5-yl)-N,N-dimethylmethanamine Chemical compound CN(C)CC1=CC2=C(NC3=C1C=CC=C3)C=CC=C2 JMGCRTKWZXSNEW-UHFFFAOYSA-N 0.000 abstract 1
XRNUHRNXIZMCIH-UHFFFAOYSA-N 1-(2,9-dichloro-11H-benzo[b][1]benzazepin-5-yl)-N,N-dimethylmethanamine Chemical compound ClC=1C=CC2=C(NC3=C(C(=C2)CN(C)C)C=CC(=C3)Cl)C1 XRNUHRNXIZMCIH-UHFFFAOYSA-N 0.000 abstract 1
IKAKEAOWHJQDSQ-UHFFFAOYSA-N 1-(2,9-dichloro-5-methylbenzo[b][1]benzazepin-11-yl)ethanone Chemical compound C(C)(=O)N1C2=C(C=C(C3=C1C=C(C=C3)Cl)C)C=CC(=C2)Cl IKAKEAOWHJQDSQ-UHFFFAOYSA-N 0.000 abstract 1
LEKLXMHRVHTZIH-UHFFFAOYSA-N 1-(2-chlorobenzo[b][1]benzazepin-11-yl)ethanone Chemical compound C(C)(=O)N1C2=C(C=CC3=C1C=CC=C3)C=CC(=C2)Cl LEKLXMHRVHTZIH-UHFFFAOYSA-N 0.000 abstract 1
PTSJWMUKAASJOV-UHFFFAOYSA-N 1-(5,6-dibromo-2-chloro-5,6-dihydrobenzo[b][1]benzazepin-11-yl)ethanone Chemical compound ClC=1C=CC2=C(N(C3=C(C(C2Br)Br)C=CC=C3)C(C)=O)C1 PTSJWMUKAASJOV-UHFFFAOYSA-N 0.000 abstract 1
GYXAGFQSEKCVIB-UHFFFAOYSA-N 1-(5-methylbenzo[b][1]benzazepin-11-yl)ethanone Chemical compound C(C)(=O)N1C2=C(C=C(C3=C1C=CC=C3)C)C=CC=C2 GYXAGFQSEKCVIB-UHFFFAOYSA-N 0.000 abstract 1
OLUOSLXXLHKQHM-UHFFFAOYSA-N 1-[5-(bromomethyl)-2,9-dichlorobenzo[b][1]benzazepin-11-yl]ethanone Chemical compound C(C)(=O)N1C2=C(C=C(C3=C1C=C(C=C3)Cl)CBr)C=CC(=C2)Cl OLUOSLXXLHKQHM-UHFFFAOYSA-N 0.000 abstract 1
RTXGWROFMKXMKB-UHFFFAOYSA-N 1-[5-(bromomethyl)-2-chlorobenzo[b][1]benzazepin-11-yl]ethanone Chemical compound ClC=1C=CC2=C(N(C3=C(C=C2CBr)C=CC=C3)C(C)=O)C1 RTXGWROFMKXMKB-UHFFFAOYSA-N 0.000 abstract 1
FJEVESSCCQDZBU-UHFFFAOYSA-N 1-[5-(bromomethyl)benzo[b][1]benzazepin-11-yl]ethanone Chemical compound BrCC1=CC2=C(N(C3=C1C=CC=C3)C(C)=O)C=CC=C2 FJEVESSCCQDZBU-UHFFFAOYSA-N 0.000 abstract 1
GPBIDTQXIMEYFB-UHFFFAOYSA-N 1-[6-(bromomethyl)-2-chlorobenzo[b][1]benzazepin-11-yl]ethanone Chemical compound ClC=1C=CC2=C(N(C3=C(C(=C2)CBr)C=CC=C3)C(C)=O)C1 GPBIDTQXIMEYFB-UHFFFAOYSA-N 0.000 abstract 1
ARXZZCMGABHGTL-UHFFFAOYSA-N 1-[6-(dimethylamino)-4-methylbenzo[b][1]benzazepin-11-yl]ethanone Chemical compound CN(C1=CC2=C(N(C3=C1C=CC=C3)C(C)=O)C=CC=C2C)C ARXZZCMGABHGTL-UHFFFAOYSA-N 0.000 abstract 1
PNCDVDWIMYCMEI-UHFFFAOYSA-N 11-benzyl-2-chloro-5-methyl-6H-benzo[b][1]benzazepin-5-ol Chemical compound ClC=1C=CC2=C(N(C3=C(CC2(O)C)C=CC=C3)CC3=CC=CC=C3)C1 PNCDVDWIMYCMEI-UHFFFAOYSA-N 0.000 abstract 1
LKAUEOQKFVQEEA-UHFFFAOYSA-N 11-benzyl-2-chloro-5-methylbenzo[b][1]benzazepine Chemical compound ClC=1C=CC2=C(N(C3=C(C=C2C)C=CC=C3)CC3=CC=CC=C3)C1 LKAUEOQKFVQEEA-UHFFFAOYSA-N 0.000 abstract 1
KOGOKDZBPJSSIL-UHFFFAOYSA-N 11-benzyl-2-chloro-5H-benzo[b][1]benzazepin-6-one hydrochloride Chemical compound ClC=1C=CC2=C(N(C3=C(C(C2)=O)C=CC=C3)CC3=CC=CC=C3)C1.Cl KOGOKDZBPJSSIL-UHFFFAOYSA-N 0.000 abstract 1
PUJNXDVXQDIMLE-UHFFFAOYSA-N 11-benzyl-2-chloro-6-methoxybenzo[b][1]benzazepine Chemical compound ClC=1C=CC2=C(N(C3=C(C(=C2)OC)C=CC=C3)CC3=CC=CC=C3)C1 PUJNXDVXQDIMLE-UHFFFAOYSA-N 0.000 abstract 1
GJPUTKWVQJEZPE-UHFFFAOYSA-N 1h-azepin-2-amine Chemical compound NC1=CC=CC=CN1 GJPUTKWVQJEZPE-UHFFFAOYSA-N 0.000 abstract 1
GBJXYEFCCOLWFW-UHFFFAOYSA-N 2-chloro-5-methyl-11H-benzo[b][1]benzazepine Chemical compound ClC=1C=CC2=C(NC3=C(C=C2C)C=CC=C3)C1 GBJXYEFCCOLWFW-UHFFFAOYSA-N 0.000 abstract 1
FCQUTDPPHFRPNJ-UHFFFAOYSA-N 2-chloro-6-methyl-11H-benzo[b][1]benzazepine Chemical compound CC1=CC2=C(NC3=C1C=CC=C3)C=C(C=C2)Cl FCQUTDPPHFRPNJ-UHFFFAOYSA-N 0.000 abstract 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 abstract 1
VOGVWOSRBPITFC-UHFFFAOYSA-N 5-methyl-11h-benzo[b][1]benzazepine Chemical compound CC1=CC2=CC=CC=C2NC2=CC=CC=C12 VOGVWOSRBPITFC-UHFFFAOYSA-N 0.000 abstract 1
206010002091 Anaesthesia Diseases 0.000 abstract 1
CKBDSSZBPFSKNX-UHFFFAOYSA-N CNC(C)C1=CC2=C(NC3=C1C=CC=C3)C=CC=C2.C(C)N(C(C)C2=CC3=C(NC1=C2C=CC=C1)C=CC=C3)CC.CN(C(C)C3=CC1=C(NC2=C3C=CC=C2)C=CC=C1)C Chemical compound CNC(C)C1=CC2=C(NC3=C1C=CC=C3)C=CC=C2.C(C)N(C(C)C2=CC3=C(NC1=C2C=CC=C1)C=CC=C3)CC.CN(C(C)C3=CC1=C(NC2=C3C=CC=C2)C=CC=C1)C CKBDSSZBPFSKNX-UHFFFAOYSA-N 0.000 abstract 1
MJMPEGGKHQJOHY-UHFFFAOYSA-N Cl.N1(CCCCC1)CC1=CC2=C(NC3=C1C=CC=C3)C=CC=C2.CNCC2=CC3=C(NC1=C2C=CC=C1)C=CC=C3 Chemical compound Cl.N1(CCCCC1)CC1=CC2=C(NC3=C1C=CC=C3)C=CC=C2.CNCC2=CC3=C(NC1=C2C=CC=C1)C=CC=C3 MJMPEGGKHQJOHY-UHFFFAOYSA-N 0.000 abstract 1
238000003747 Grignard reaction Methods 0.000 abstract 1
TUCNEACPLKLKNU-UHFFFAOYSA-N acetyl Chemical compound C[C]=O TUCNEACPLKLKNU-UHFFFAOYSA-N 0.000 abstract 1
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 abstract 1
239000012346 acetyl chloride Substances 0.000 abstract 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 abstract 1
150000001263 acyl chlorides Chemical class 0.000 abstract 1
230000010933 acylation Effects 0.000 abstract 1
238000005917 acylation reaction Methods 0.000 abstract 1
230000001476 alcoholic effect Effects 0.000 abstract 1
125000000217 alkyl group Chemical group 0.000 abstract 1
125000000746 allylic group Chemical group 0.000 abstract 1
150000001412 amines Chemical class 0.000 abstract 1
230000037005 anaesthesia Effects 0.000 abstract 1
238000001949 anaesthesia Methods 0.000 abstract 1
230000002082 anti-convulsion Effects 0.000 abstract 1
230000001430 anti-depressive effect Effects 0.000 abstract 1
230000001387 anti-histamine Effects 0.000 abstract 1
239000007864 aqueous solution Substances 0.000 abstract 1
XYOVOXDWRFGKEX-UHFFFAOYSA-N azepine Chemical compound N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 abstract 1
235000019445 benzyl alcohol Nutrition 0.000 abstract 1
KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 abstract 1
229940073608 benzyl chloride Drugs 0.000 abstract 1
230000031709 bromination Effects 0.000 abstract 1
238000005893 bromination reaction Methods 0.000 abstract 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
229910052794 bromium Inorganic materials 0.000 abstract 1
239000003795 chemical substances by application Substances 0.000 abstract 1
125000001309 chloro group Chemical group Cl* 0.000 abstract 1
238000006264 debenzylation reaction Methods 0.000 abstract 1
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 abstract 1
XNTYINWAOZRMSU-UHFFFAOYSA-N ethyl N-(11H-benzo[b][1]benzazepin-5-ylmethyl)-N-methylcarbamate Chemical compound C(C)OC(=O)N(C)CC1=CC2=C(NC3=C1C=CC=C3)C=CC=C2 XNTYINWAOZRMSU-UHFFFAOYSA-N 0.000 abstract 1
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 abstract 1
238000010438 heat treatment Methods 0.000 abstract 1
125000000623 heterocyclic group Chemical group 0.000 abstract 1
230000003301 hydrolyzing effect Effects 0.000 abstract 1
150000002576 ketones Chemical class 0.000 abstract 1
VXWPONVCMVLXBW-UHFFFAOYSA-M magnesium;carbanide;iodide Chemical compound [CH3-].[Mg+2].[I-] VXWPONVCMVLXBW-UHFFFAOYSA-M 0.000 abstract 1
WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical group [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 abstract 1
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 abstract 1
150000007522 mineralic acids Chemical class 0.000 abstract 1
BAVYZALUXZFZLV-UHFFFAOYSA-N mono-methylamine Natural products NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 abstract 1
229910052757 nitrogen Inorganic materials 0.000 abstract 1
125000004430 oxygen atom Chemical group O* 0.000 abstract 1
230000003389 potentiating effect Effects 0.000 abstract 1
229940125723 sedative agent Drugs 0.000 abstract 1
230000001624 sedative effect Effects 0.000 abstract 1
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 abstract 1
239000007858 starting material Substances 0.000 abstract 1
125000001424 substituent group Chemical group 0.000 abstract 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 abstract 1
230000001131 transforming effect Effects 0.000 abstract 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1

Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients

Landscapes

Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Epidemiology (AREA)
Life Sciences & Earth Sciences (AREA)
Chemical & Material Sciences (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Other In-Based Heterocyclic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

ES0294340A 1962-12-04 1963-12-03 Procedimiento para la preparaciën de nuevos derivados azepinicos Expired ES294340A1 (es)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH1421662A CH412906A (de)	1962-12-04	1962-12-04	Verfahren zur Herstellung von neuen Azepinderivaten

Publications (1)

Publication Number	Publication Date
ES294340A1 true ES294340A1 (es)	1964-06-01

Family

ID=4398918

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
ES0294340A Expired ES294340A1 (es)	1962-12-04	1963-12-03	Procedimiento para la preparaciën de nuevos derivados azepinicos
ES0294339A Expired ES294339A1 (es)	1962-12-04	1963-12-03	Procedimiento para la preparaciën de nuevos derivados azepinicos

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
ES0294339A Expired ES294339A1 (es)	1962-12-04	1963-12-03	Procedimiento para la preparaciën de nuevos derivados azepinicos

Country Status (10)

Country	Link
AT (2)	AT242159B (2)
BE (1)	BE640820A (2)
BR (1)	BR6355096D0 (2)
CH (2)	CH416645A (2)
DE (2)	DE1795513A1 (2)
DK (2)	DK107293C (2)
ES (2)	ES294340A1 (2)
FI (2)	FI42560B (2)
GB (1)	GB1038914A (2)
NL (2)	NL125064C (2)

0
- NL NL301291D patent/NL301291A/xx unknown
- NL NL125064D patent/NL125064C/xx active
1962
- 1962-11-04 CH CH564066A patent/CH416645A/de unknown
- 1962-12-04 CH CH1421662A patent/CH412906A/de unknown
1963
- 1963-12-02 FI FI2374/63A patent/FI42560B/fi active
- 1963-12-03 DE DE19631795513 patent/DE1795513A1/de active Pending
- 1963-12-03 AT AT460764A patent/AT242159B/de active
- 1963-12-03 DK DK564863AA patent/DK107293C/da active
- 1963-12-03 AT AT968063A patent/AT243274B/de active
- 1963-12-03 DK DK161965AA patent/DK107750C/da active
- 1963-12-03 BR BR155096/63A patent/BR6355096D0/pt unknown
- 1963-12-03 ES ES0294340A patent/ES294340A1/es not_active Expired
- 1963-12-03 DE DE19631445826D patent/DE1445826B1/de active Pending
- 1963-12-03 ES ES0294339A patent/ES294339A1/es not_active Expired
- 1963-12-03 GB GB47592/63A patent/GB1038914A/en not_active Expired
- 1963-12-04 BE BE640820D patent/BE640820A/xx unknown
1969
- 1969-10-06 FI FI2873/69A patent/FI42562B/fi active

Also Published As

Publication number	Publication date
AT243274B (de)	1965-11-10
DK107293C (da)	1967-05-16
NL301291A (2)
DE1795513A1 (de)	1972-01-13
BR6355096D0 (pt)	1973-07-19
FI42560B (2)	1970-06-01
GB1038914A (en)	1966-08-10
NL125064C (2)
BE640820A (2)	1964-06-04
DK107750C (da)	1967-07-03
CH416645A (de)	1966-07-15
ES294339A1 (es)	1964-05-16
DE1445826B1 (de)	1970-11-19
FI42562B (2)	1970-06-01
AT242159B (de)	1965-09-10
CH412906A (de)	1966-05-15

Publication	Publication Date	Title
GB959994A (en)	1964-06-03	Basically substituted compounds and a process for their production
NZ209166A (en)	1987-07-31	1-piperazinecarboxamides and pharmaceutical compositions
FI66374C (fi)	1984-10-10	Foerfarande foer framstaellning av terapeutiskt aktiva 3-fluor-10-piperazino-8-substituerade 10,11-dihydrodibenso(b f)tiepiner
US4235775A (en)	1980-11-25	Triazolobenzodiazepine derivatives
US2666050A (en)	1954-01-12	Process of producing them
CA2189760A1 (en)	1996-09-19	Pyrrolocarbazole derivatives
ES294340A1 (es)	1964-06-01	Procedimiento para la preparaciën de nuevos derivados azepinicos
IE44316B1 (en)	1981-10-21	Indazole derivatives
GB1562800A (en)	1980-03-19	Fused pyridodiazepines
US3636046A (en)	1972-01-18	Derivatives of dibenzo(b f)pyrrolo(3 4-d)azepine
CS242088A2 (en)	1990-09-12	Method of 1-cyclopropyl-7-substituted-6-fluor-4-oxo-1,4-dihydroquinoline-3-carboxylic acid's derivatives production
EP0019866B1 (en)	1984-03-14	Process for the preparation of 10,11-dihydro-5h-dibenzo (a,d)cyclohepten-5,10-imines
DE1720033A1 (de)	1971-05-19	Neue Indolderivate und Verfahren zu ihrer Herstellung
US3383382A (en)	1968-05-14	N-amino-iminodibenzyl
US3646146A (en)	1972-02-29	Diphenylcyclopropyl-methyl-amines
US3467755A (en)	1969-09-16	Compositions and methods for producing sedation and tranquilization with substituted 4,5,6,7- tetrahydro-4-oxindoles
US4235921A (en)	1980-11-25	Treating muscular spasms and convulsions with 3-azabicyclo[3.1.0]hexanes
GB1596170A (en)	1981-08-19	1,2,3,4,4a,10b-hexahydro-benz(f)isouqinolines
NO753672L (2)	1976-05-05
Hertler et al.	1959	Synthesis of 3, 8-Endomethylene-3-azabicyclo [3.2. 1]-octane (Cyclocamphidine)
US3532722A (en)	1970-10-06	Spiro(dibenzo(a,d) (1,4) cycloheptadiene-5-4' - tetrahydrofurfurylamine) and mono- and dialkylated derivatives and their salts
US3646038A (en)	1972-02-29	1-(n-methylpiperazineacetyl)aminofluorene
US3739030A (en)	1973-06-12	2-hydroxy-5-amino-benzamide derivatives
US3711484A (en)	1973-01-16	Derivatives of n-methylpiperazine
GB962461A (en)	1964-07-01	Substituted 5h-dibenz[b, f] azepines and processes for their production