NZ206992A - 5-(3-aminopropyl)-11-phenyl-5h-dibenzo(b,e)(1,4)-diazepines - Google Patents
5-(3-aminopropyl)-11-phenyl-5h-dibenzo(b,e)(1,4)-diazepinesInfo
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- NZ206992A NZ206992A NZ20699281A NZ20699281A NZ206992A NZ 206992 A NZ206992 A NZ 206992A NZ 20699281 A NZ20699281 A NZ 20699281A NZ 20699281 A NZ20699281 A NZ 20699281A NZ 206992 A NZ206992 A NZ 206992A
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Description
New Zealand Paient Spedficaiion for Paient Number £06992
206992
Priority Date(s): ft. $
Complete Specification Filed:
Class:
21 FpViftM
Publication Date:
P.O. Journal, No: ..
Under the provisions of RegU9
liition 23 (I) the
„
Specification bas been ante-dated] to ^LJ^£eLg42SL. I9i7
21 FES —" ^
Patents Form No. 5
3/
St{ Y%V.
NEW ZEALAND PATENTS ACT 195 3 COMPLETE SPECIFICATION
"5-(AMINO-ALKYL)-11-PHENYL-5H-DIBENZO [b,e][l,4] DIAZEPINES"
WE, A.H. ROBINS COMPANY, INC. a corporation organised under the laws of the State of Virginia, U.S.A. of 1407 Cummings Drive, Richmond, Virginia 23220, U.S.A. hereby declare the invention for which we pray that a patent may be granted to us, and the method by which it is to be performed, to be particularly described in and by the following statement
206992
-(AMINOALKYL)-11-PHENYL-5H-DIBENZO [b,e][1,4]DIAZEPINES
BACKGROUND OF THE INVENTION
1. Field of Invention.
The present invention relates to novel 5-(aminoalkyl)-ll-phenyl-5H-dibenzo[b,e][l,43diazepines and a process for their production.
2. Description of the Prior Art.
Wander, A. in British Patent 907,646 discloses preparation of certain of the dibenzodiazepines utilized in the method of this invention; e.g., the active ingredient of the compound of example 1 below in the form of the maleate salt.
Wander, A. in British Patent 959,994 discloses utility of reduced forms; e.g., 5-(aminoalkyl)-ll-phenyl-10,ll-dihydro-5H-dibenzo[b,e][l,4]diazepines as parasympathologics, antihistamines, spasmolytics, tranquillizers and psychic energizers.
Greig, M.E., et al, in J. Med. Chem. 14, No. 2 page 153 (1971) discloses anaphylaxis activity of certain dibenzodiazepine homologs in mice particularly 2-chloro-5-[2-(dimethylamino)ethyl]-ll-phenyl-5H-dibenzo[b,e][l,43d:
206992.
SUMMARY OF THE INVENTION In accordance with this invention there are provided compounds having the formula:
other is hydrogen, and
X is selected from the group consisting of hydrogen, chlorine, bromine and fluorine,
and the pharmaceutically acceptable acid addition salts thereof; and other compounds as specifically set forth in the Examples 2, and. 4 to 7 herein having the above::formula in which
2
and R are both methyl,
and X is as defined above, and including those specific salts also set forth in the Examples 2, and 4 to 7.
Pharmaceutically acceptable acid addition salts are those salts which are physiologically compatible, such salts being formed either by strong or weak acids. Representative of strong acids are hydrochloric, sulfuric and phosphoric acids. Representative of weak acids are fumaric, maleic, succinic, oxalic, cyclohexamic, and the like.
The compounds of this invention have antidepressant
X
Formula i
(ch2)3nr1r2
1 2
wherein r and r are both hydrogen or one is methyl and the utility. The use of the compounds in such utility is
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described and claimed in New Zealand Patent Specification No. 198986 from which this specification has been divided.
The compounds of this invention wherein the 5-position in formula I is substituted by the 3-dimethylaminopropyl radical are prepared by cyclodehydration of the N-(3-dimethylaminopropyl )-o-benzamido-diphenylamines as in British Patent 907,646 using a dehydrating-condensation catalyst; for example, phosphorus pentoxide or oxyhalogenides of phosphorus, preferably the latter, in a suitable solvent; e.g., 1,1,2,2-tetrachoroethane. The equation is:
wherein X has the values assigned under Formula I above.
The novel compounds of this invention wherein the 5-position in formula I is substituted by the 3-aminopropyl radical are prepared by cyclodehydration of novel N-[3-(l-phthalimido)propylJ-o-benzamido-diphenylamines (lib) and thereafter converting the phthalimido moiety to amino (NHj) with hydrazine and acid. The equation is:
DETAILED DESCRIPTION OF THE INVENTION
x n(ch3)2
la
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wherein X has the values assigned under Formula I. Compounds of Formula III are also novel. Compounds of Formula lib are described and claimed in New Zealand Patent Specification No. which has also been divided from N.Z. Patent
Specification No. 198986
The novel compounds of the invention wherein the 5-position in Formula I is substituted by 3-monomethylpropyl amine are prepared by further reaction of the 3-aminopropyl compound with triethylorthoformate followed by reaction with sodium borohydride (procedure of Crocket & Blanton, 1974(1): 55-6 Synthesis). The equation is as follows:
1) (EtO)aCH
2) NaBH4
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The starting benzamido compounds II (Ila and lib) are prepared by a modification of the procedure of British Patent 907,646. Ortho-nitro-diphenylamine is first reductively alkylated with a solution of B-chloropropyl dimethylamine or 3-(l-phthalimido)-l-chloropropane and following this the nitro moiety is reduced with hydrogen over palladium on carbon to given the corresponding ortho amino compound. The amino radical in the ortho position is then reacted with a benzoyl halide or a substituted benzoyl halide. The equation is as follows;
o2n vi
NaH
ci-(ch2)3q
02n
Pyridine j,
V
IV
O
n . C-Cl ii
( CH2 ) 3 t q
Q = -NCCH^^ or 1-phthalimido.
^ ■
29 AUG 198$
v
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Preparation 1 N-(3-Dimethylaminopropyl)-o-aminodiphenylamine.
A mixture of 32.0 g (0.107 mole) of N-(3-dimethylamino-propyl^-o-nitrodiphenylamine (b.p. 155°/0.4 to 174°C./ 0.33 mm), 100 ml of 200 proof ethyl alcohol and 1.5 g of 10% palladium-on-carbon catalyst was shaken under hydrogen atmosphere at room temperature of 1 hour. After approximately the theoretical amount of hydrogen was absorbed the catalyst was filtered off through a celite filter cake and solvent removed under reduced pressure. The residue was distilled under high vacuum as follows:
b.p.,°C. Amt.,g
Fraction 1 80-130°/0.2 mm 4.0
2 130-137°0.2 mm 7.0
3 137-142°/0.2 mm 15.5
Thin layer chromatography using 20% methyl alcohol - 80% benzene on silica gel, showed Fraction 3 to be quite pure.
Preparation 2 N-(3-Dimethylaminopropyl)-o-benzamidodiphenylamine.
To a solution of 15.5 g (0.0575 mole) of N-(3-dimethyl-aminopropyl)-o-aminodiphenylamine in 100 ml of pyridine cooled to about 5°C. under nitrogen atmosphere was added 17.8 g (0.063 mole) of benzoyl chloride. A small amount of benzene was used to wash the remaining benzoyl chloride into the reaction vessel. The mixture was stirred for 1 hr and the vessel stoppered and placed in the refrigerator over the wej
I
JUt1985 ;!
206992
The solvent was then evaporated under reduced pressure. The residual oil was dissolved in 100 ml of methylene chloride and the solution washed once with 150 ml of 3 N sodium hydroxide and three times with 250 ml of water. The methylene chloride layer was dried over magnesium sulfate and evaporated under reduced pressure. Residual pyridine was then removed under high vacuum (0.2 mm Hg) overnight. Weight of the residual oil, the free base, was 24.9 g.
Oxalate Salt - To a hot solution of 4.0 g of the free base in isopropyl alcohol was added 1.35 g (0.0107 mole) of oxalic acid dihydrate. The precipitated oxalate salt of the title compound weighed 3.5 g and melted at 162-5°C. The salt after drying 1 hr at 97-98°C. (refluxing propyl alcohol) and overnight at room temperature all at 0.1 mm Hg., analyzed as follows:
Analysis: Calculated for C26H29N3°5: C'67-37* H,6.31; N,9.06 Found : C,67.42; H,6.35; N,9.01
Preparation 3
Following the procedure of Preparation 2 and substituting the following for benzoyl chloride:
2-chloro-benzoyl chloride,
3-chloro-benzoyl chloride,
2-fluoro-benzoyl chloride,
3-fluoro-benzoyl chloride,
2-bromo-benzoyl chloride,
3-bromo-benzoyl chloride, and
4-chloro-benzoyl chloride,
206392
there are obtained:
N-(3-dimethylaminopropyl)-o-(2-chlorobenzamido) diphenylamine,
N-(3-dimethylaminopropyl)-o-(3-chlorobenzamido) diphenylamine,
N-(3-dimethylaminopropyl)-o-(2-fluorobenzamido) diphenylamine^
N-(3-dimethylaminopropyl)-o-(3-fluorobenzamido) diphenylamine,
N-(3-dimethylaminopropyl)-o-(2-bromobenzamido) diphenylamine,
N-(3-dimethylaminopropyl)-o-(3-bromobenzamido) diphenylamine, and
N-(3-dimethylaminopropyl)-o-(4-chlorobenzamido) diphenylamine.
Preparation 4 N-[3-(1-Phthalimido)propylJ-o-aminodiphenylamine. o-Nitrodiphenylamine is reacted with sodium hydride and 3-(l-phthalimido)-l-chloropropane to give N-3-(l-phthalimido)-propyl-o-nitrodiphenylamine which is then reduced with hydrogen over palladium-on-carbon in ethanol to give the title compound.
Preparation 5 When in the procedure of Preparation 2, N-3-(l-phthalimido)propyl-o-aminodiphenylamine is reacted with each of the following acyl chlorides in excess in the manner of Preparation 2:
1 5JUL1985 v
Xn.-'
206992
2-chloro-benzoyl chloride,
3-chloro-benzoyl chloride,
2-fluoro-benzoyl chloride,
3-fluoro-benzoyl chloride,
2-bromo-benzoyl chloride,
3-bromo-benzoyl chloride, and
4-chloro-benzoyl chloride,
there are obtained:
N-3-(l-phthalimido)propyl-o-(2-chlorobenzamido) diphenylamine,
N-3-(l-phthalimido)propyl-o-(3-chlorobenzamido) diphenylamine,
N-3-(1-phthalimido)propyl-o-(2-fluorobenzamido) diphenylamine,
N-3-(1-phthalimido)propyl-o-(3-fluorobenzamido) diphenylamine,
N-3-(1-phthalimido)propyl-o-(2-bromobenzamido) diphenylamine,
N-3-(1-phthalimido)propyl-o-(3-bromobenzamido) diphenylamine, and
N-3-(1-phthalimido)propyl-o-(4-chlorobenzamido) diphenylamine.
The following examples will illustrate compounds of the invention and processes for producing such compounds. The compound of Example 1 is not a part of this invention being described and claimed in New Zealand Patent Specificatio no. 2c(#9o which has also been divided from No. 19898
20699
- n -
Example 1
-(3-Dimethylaminopropyl)-ll-phenyl-5H-dibenzo [b,e][l,43diazepine, fumarate £1:13.
A stirred mixture of 18.9 g (0.05 mole) of N-(3-dimethylaminopropyl)-o-benzamidodiphenylamine and 32.19 g (0.2 mole) of phosphorus oxychloride in 50 ml of 1,1,2,2-tetrachloroethane was heated at 150°C under nitrogen atmosphere for 1.5 hr. The mixture was cooled somewhat and poured over aproximately 1000 ml of crushed ice and then diluted with enough water for a final volume of 1000 ml. The aqueous suspension was extracted twice with methylene chloride and the methylene chloride layer discarded. The aqueous layer was basified with 3 N sodium hydroxide and extracted with three - 250 ml portions of methylene chloride. These three methylene chloride washes were combined, dried over magnesium sulfate and evaporated under reduced pressure to give a residual oil weighing 13.8 g, the free base of the title compound. The oil was dissolved in hot isopropyl alcohol and reacted with 4.5 g (0.039 mole) of fumaric acid. The fumarate salt was collected by filtration, yielding 13 g when dried, m.p. 168-170°C.
Analysis: Calculated for C28H29N3°4: C,71.32; H,6.20;
N,8.91
Found : C,71.19; H6.19;
N8.89
Example 2
Following the procedure of Example 1 and substituting equal molar amounts of the following for N-(3-dimethylaminopropyl )-o-benzamidodiphenylamine:
u
N-(3-dimethylaminopropyl)-o-(2-chlorobenzamido) diphenylamine,
N-(3-dimethylaminopropyl)-o-(3-chlorobenzamido) diphenylamine,
N-(3-dimethylaminopropyl)-o-(2-fluorobenzamido) diphenylamine,
N-(3-dimethylaminopropyl)-o-(3-fluorobenzamido) diphenylamine,
N-(3-dimethylaminopropyl)-o-(2-bromobenzamido) diphenylamine,
N-(3-dimethylaminopropyl)-o-(3-bromobenzamido) diphenylamine, and
N-(3-dimethylaminopropyl)-o-(4-chlorobenzamido) diphenylamine,
there are obtained:
11- (2-chlorophenyl) -5-? (3-dimethylaminopropyl) -5H-dibenzo [b,e][1,4jdiazepine, fumarate,
11-(3-chlorophenyl)-5-(3-dimethylaminopropyl)-5H-dibenzo [b,e][1,4]diazepine, fumarate,
11-(2-fluorophenyl)-5-(3-dimethylaminopropyl)-5H-dibenzo [b,ej[l,4]diazepine, fumarate,
11-(3-fluorophenyl)-5-(3-dimethylaminopropyl)-5H-dibenzo [b,e][1,4]diazepine, fumarate,
11-(2-bromophenyl)-5-(3-dimethylaminopropyl)-5H-dibenzo [b,e][l,43diazepine, fumarate,
11-(3-bromophenyl)-5-(3-dimethylaminopropyl)-5H-dibenzo [b,eJCl,4jdiazepine, fumarate, and
20699
11-(4-chlorophenyl)-5-(3-dimethylaminopropyl)-5H-dibenzo [b,e][l,4]diazepine, fumarate.
Example 3
When in the procedure of Example 1 prior to addition of fumaric acid, the following are substituted for N-(3-dimethylaminopropyl)-o-benzamidodiphenylamine:
N-3-(1-phthalimido)propyl-o-benzamidodiphenylamine, N-3-(1-phthalimido)propyl-o-(2-chlorobenzamido) diphenylamine,
N-3-(1-phthalimido)propyl-o-(3-chlorobenzamido) diphenylamine,
N-3-(1-phthalimido)propyl-o-(2-fluorobenzamido) diphenylamine,
N-3-(1-phthalimido)propyl-o-(3-fluorobenzamido) diphenylamine,
N-3-(l-phthalimido)propyl-o-(2-bromobenzamido) diphenylamine,
N-3-(1-phthalimido)propyl-o-(3-bromobenzamido) diphenylamine, and
N-3-(1-phthalimido)propyl-o-(4-chlorobenzamido) diphenylamine,
there are obtained:
-[3-(1-phthaiimido)propyl]-ll-phenyl-5H-dibenzo Cb,e]£l,4]diazepine,
-[3-(1-phthalimido)propyl]-11-(2-chlorophenyl)-5H-dibenzoEb,e][l,4]diazepine,
i
-[3-(l-phthalimido)propyl]-ll-(3-chlorophenyl)-5H-dibenzo[b,e]Cl,4]diazepine,
206992-
14
-[3-(1-phthalimido)propyl]-11-(2-fluorophenyl)-5H-dibenzo[b,e][1,4]diazepine,
-[3-(1-phthalimido)propyl]-11-(3-fluorophenyl)-5H-dibenzo[b,e][1,4]diazepine
-[3-(1-phthalimido)propyl]-11-(2-bromophenyl)-5H-dibenzoCb,e][l,4]diazepine,
-[3-(1-phthalimido)propyl]-11-(3-bromophenyl)-5H-dibenzoCb,e][1,4]diazepine, and
-[3-(1-phthalimido)propyl]-11-(4-chlorophenyl)-5H-dibenzoCb,e][l,4]diazepine.
-(3-Aminopropyl)-ll-phenyl-5H-dibenzo[b,e][1,4]
diazepine hydrochloride.
A mixture of 0.035 mole of 5-[3-(l-phthalimido)propyl-ll-phenyl-5H-dibenzo[b,e][1,4]diazepine, 0.039 mole of hydrazine hydrate and 175 ml of 190 proof ethyl alcohol is refluxed for 2.5 hr and allowed to stand for several hours. A solution of 10 ml concentrated hydrochloric acid in 50 ml water is added to the mixture and the mixture is stirred for several hours. The mixture is filtered and the filtrate evaporated under reduced pressure. The hydrochloride salt is isolated by recrystallization from a suitable solvent and dried under reduced pressure.
Following the procedure of Example 4 and substituting equal molar amounts of the following for 5-[3-(1-phthalimido) propyl]-11-phenyl-5H-dibenzo[b,e][l,4]diazepine:
Example 4
Example 5
11-(2-chlorophenyl)-5-[3-(1-phthalimodo)propyl]-5H' dibenzoCb,e]Cl/4]diazepine,
11-(3-chlorophenyl)-5-[3-(1-phthalimido)propyl]-5H-dibenzoCb,e]Cl,4]diazepine,
11-(2-fluorophenyl)-5-[3-(1-phthalimido)propyl]-5H-dibenzoCb,e][l,4]diazepine,
11-(3-fluorophenyl)-5-[3-(1-phthalimido)propyl]-5H-dibenzoCb,e][l,4]diazepine,
11-(2-bromophenyl)-5-[3-(1-phthalimido)propyl]-5H-dibenzoCb,e]Cl, 4]diazepine,
11-(3-bromophenyl)-5-[3-(1-phthalimido)propyl]-5H-dibenzoCb,e]Cl,4]diazepine, and
11-(4-chlorophenyl)-5-C3-(1-phthalimido)propyl]-5H dibenzoCb,e][l,4]diazepine,
there are obtained:
-(3-aminopropyl)-11-(2-chlorophenyl)-5H-dibenzo Cb,e]£l,4]diazepine hydrochloride,
-(3-aminopropyl)-11—(3-chlorophenyl)-5H-dibenzo Eb,e]Cl,4]diazepine hydrochloride,
-(3-aminoproply)-11-(2-fluorophenyl)-5H-dibenzo [b,e]Cl,4]diazepine hydrochloride,
-(3-aminopropyl)-11-(3-fluorophenyl)-5H-dibenzo Cb,e]Cl,4]diazepine hydrochloride,
-(3-aminopropyl)-11-(2-bromophenyl)-5H-dibenzo Cb,e]Cl»4]diazepine hydrochloride,
-(3-aminopropyl)-11-(3-bromophenyl)-5H-dibenzo Cb,e]Cl/4]diazepine hydrochloride, and
20399
-(3-aminopropyl)-11-(4-chlorophenyl)-5H-dibenzo [b,e3[l,4]diazepine hydrochloride.
Example 6
N-Methyl-ll-phenyl-5H-dibenzo[b,e]Cl,4Jdiazepin-5-propanamine, hydrochloride.
The hydrochloride salt of 5-(3-aminopropyl)-ll-phenyl-5H-dibenzo[b,e][l,4]diazepine is converted to the free base by partitioning between dilute sodium hydroxide and methylene chloride, drying and concentrating the methylene chloride layer to dryness adding dry benzene and again concentrating to drive off the benzene. The resulting free base is dissolved in a large excess of freshly distilled triethylorthoformate with refluxing for several hours. The mixture is concentrated in vacuo, ethanol is added and the mixture concentrated again. The resulting imidate is dissolved in ethanol and sodium borohydride is added with stirring at 15-20°C until thin-layer chromatography indicates the absence of substantial amount of starting material. The mixture is cooled and gradually flooded with water followed by extraction with ethylacetate. The ethylacetate layer is washed to neutrality and salted, filtered and evaporated. Crude free base is isolated by column chromatography and reacted with ethereal hydrogen chloride and recrystallized to give the title compound.
Example 7
Following the procedure of Example 6 and substituting equal molar amounts of the following for 5-(3-aminopropyl)-ll-phenyl-5H-dib^nzo£b,e]Cl/4]diazepine:
20699
-(3-aminopropyl)-11-(2-chlorophenyl)-5H-dibenzo Cb,e][1,4]diazepine hydrochloride,
-(3-aminopropyl)-11-(3-chlorophenyl)-5H-dibenzo Cb,e]Cl/4]diazepine hydrochloride,
-(3-aminopropyl)-11-(2-fluorophenyl)-5H-dibenzo Cb/e]Cl/4]diazepine hydrochloride,
-(3-aminopropyl)-11-(3-fluorophenyl)-5H-dibenzo Cb,e]Cl»4]diazepine hydrochloride,
-(3-aminopropyl)-11-(2-bromophenyl)-5H-dibenzo Cb,e]Cl/4]diazepine hydrochloride,
-(3-aminopropyl)-11-(3-bromophenyl)-5H-dibenzo Cb,e]Cl/4]diazepine hydrochloride, and
-(3-aminopropyl)-11-(4-chlorophenyl)-5H-dibenzo Cb,e]Cl»4]diazepine hydrochloride,
there are obtained:
11-(2-chlorophenyl)-N-methyl-5H-dibenzoCb,e]Cl# 4] diazepin-5-propanamine hydrochloride,
11-(3-chlorophenyl)-N-methyl-5H-dibenzoCb,e]Cl/4] diazepin-5-propanamine hydrochloride,
11-( 2-fluorophenyl)-N-methyl-5H-dibenzoCb,e]C1» 4] diazepin-5-propanamine hydrochloride,
11-(3-fluorophenyl)-N-methyl-5H-dibenzoCb,e]C1/4] diazepin-5-propanamine hydrochloride,
11-(2-bromophenyl)-N-methyl-5H-dibenzoCb,e]C1/4] diazepin-5-propanamine hydrochloride,
11-(3-bromophenyl)-N-methyl-5H-dibenzoCb,e]Cl/4] diazepin-5-propanamine hydrochloride, and
11-(4-chlorophenyl)-N-methyl-5H-dibenzoCb,e]Cl/4] diazepin-5-propanamine hydrochloride.
206992
Claims (5)
1. A compound selected from those having the formula: (CH2)3NR1R2 wherein X is selected from the group consisting of hydrogen, 1 2 chlorine, bromine and fluorine, and R and R are both hydrogen 1 2 or R is hydrogen when R is methyl, and the pharmaceutically acceptable acid addition salts thereof and from those compounds having the above formula wherein X is as defined 1 2 above and R and R are both amt methyl and the acid addition salts thereof which are specifically set forth herein in any one of Examples 2, and 4 to 7.
2. A compound selected from those having the formula: 9stPfl85 ( CHg ) 3NRJR2 wherein X is selected from the group consisting of hydrogen, chlorine, bromine and fluorine, and Rl and R2 are both 206992 - 19 - 1 . 2 hydrogen or R is hydrogen when R is methyl, and the pharmaceutically acceptable acid addition salts thereof.and—- 4-V.^r.r. nnmpAMr^^lr fftQ aKni.o p whprpin Y IB a C_ 1 O _ defined Above ana k ana K age lhd^p^iKlfctully aclootod from -lyydiuym'i and methyl and Ui5 ai'id addition oaltc thereof^
3. A process for producing a compound as claimed in 1 2 claim 1 wherein both R and R are methyl groups comprising cyclodehydrating a compound of the formula Ila: Ila (ch2) 3 n(ch3)2 in the presence of a suitable catalyst and in a suitable solvent.
4. A process for producing a compound as claimed in 1 2 claim 1 wherein both R and R are hydrogen atoms comprising cyclodehydrating a compound of Formula lib; O^Nvo lib 8 f 15JULI985 206992 - 20 - in the presence of a suitable catalyst and in a suitable solvent, and then reacting the resulting compound with hydrazine in the presence of an acid.
5. A process for preparing a compound as claimed in 1 2 claim 1 where R is hydrogen and R is methyl comprising 1 2 reacting a corresponding compound where both R and R are hydrogen with ethylorthoformate and then with sodium borohydride. A.H. ROBINS COMPANY By their Attorneys BALDWIN, SON & CAREY
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US30507681A | 1981-09-24 | 1981-09-24 | |
| NZ198986A NZ198986A (en) | 1981-09-24 | 1981-11-17 | Anti-depressant compositions containing certain 5-(3-amino-propyl)-11-phenyl-5h-dibenzo(b,e)(1,4)-diazepines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NZ206992A true NZ206992A (en) | 1986-02-21 |
Family
ID=26650497
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NZ20699281A NZ206992A (en) | 1981-09-24 | 1981-11-17 | 5-(3-aminopropyl)-11-phenyl-5h-dibenzo(b,e)(1,4)-diazepines |
| NZ20699081A NZ206990A (en) | 1981-09-24 | 1981-11-17 | 5-(3-dimethylaminopropyl)-11-phenyl-5h-dibenzo-(b,e)(1,4)-diazepine,fumarate(1:1) |
| NZ20699181A NZ206991A (en) | 1981-09-24 | 1981-11-17 | N-(3-(phthal-1-imido)propyl)-o-benzamidodiphenylhlamines |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NZ20699081A NZ206990A (en) | 1981-09-24 | 1981-11-17 | 5-(3-dimethylaminopropyl)-11-phenyl-5h-dibenzo-(b,e)(1,4)-diazepine,fumarate(1:1) |
| NZ20699181A NZ206991A (en) | 1981-09-24 | 1981-11-17 | N-(3-(phthal-1-imido)propyl)-o-benzamidodiphenylhlamines |
Country Status (1)
| Country | Link |
|---|---|
| NZ (3) | NZ206992A (en) |
-
1981
- 1981-11-17 NZ NZ20699281A patent/NZ206992A/en unknown
- 1981-11-17 NZ NZ20699081A patent/NZ206990A/en unknown
- 1981-11-17 NZ NZ20699181A patent/NZ206991A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NZ206990A (en) | 1986-02-21 |
| NZ206991A (en) | 1986-02-21 |
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