US2802004A - Derivatives of 3-aza-bicyclo (3: 2: 0) heptane-2, 4-dione - Google Patents
Derivatives of 3-aza-bicyclo (3: 2: 0) heptane-2, 4-dione Download PDFInfo
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- US2802004A US2802004A US539653A US53965355A US2802004A US 2802004 A US2802004 A US 2802004A US 539653 A US539653 A US 539653A US 53965355 A US53965355 A US 53965355A US 2802004 A US2802004 A US 2802004A
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- United States
- Prior art keywords
- heptane
- dione
- azabicyclo
- imide
- matter
- Prior art date
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- ILPNRWUGFSPGAA-UHFFFAOYSA-N heptane-2,4-dione Chemical compound CCCC(=O)CC(C)=O ILPNRWUGFSPGAA-UHFFFAOYSA-N 0.000 title description 6
- 150000001875 compounds Chemical class 0.000 claims description 15
- 239000000203 mixture Substances 0.000 claims description 14
- 150000003839 salts Chemical group 0.000 description 18
- 150000003949 imides Chemical class 0.000 description 17
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- 238000000034 method Methods 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 6
- 150000008064 anhydrides Chemical class 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 150000002431 hydrogen Chemical class 0.000 description 4
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 238000005292 vacuum distillation Methods 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- MZVQCMJNVPIDEA-UHFFFAOYSA-N [CH2]CN(CC)CC Chemical group [CH2]CN(CC)CC MZVQCMJNVPIDEA-UHFFFAOYSA-N 0.000 description 2
- 230000003444 anaesthetic effect Effects 0.000 description 2
- 230000002921 anti-spasmodic effect Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 230000000973 chemotherapeutic effect Effects 0.000 description 2
- 239000000812 cholinergic antagonist Substances 0.000 description 2
- 239000002178 crystalline material Substances 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- -1 dialkylaminoalkyl imides Chemical class 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000003589 local anesthetic agent Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- SUSAGCZZQKACKE-ZXZARUISSA-N (1s,2r)-cyclobutane-1,2-dicarboxylic acid Chemical compound OC(=O)[C@H]1CC[C@H]1C(O)=O SUSAGCZZQKACKE-ZXZARUISSA-N 0.000 description 1
- NMNZZIMBGSGRPN-ZXZARUISSA-N (1s,5r)-3-oxabicyclo[3.2.0]heptane-2,4-dione Chemical compound O=C1OC(=O)[C@@H]2CC[C@H]12 NMNZZIMBGSGRPN-ZXZARUISSA-N 0.000 description 1
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 1
- XSJVWZAETSBXKU-UHFFFAOYSA-N 2-ethoxypropane Chemical compound CCOC(C)C XSJVWZAETSBXKU-UHFFFAOYSA-N 0.000 description 1
- UIKUBYKUYUSRSM-UHFFFAOYSA-N 3-morpholinopropylamine Chemical compound NCCCN1CCOCC1 UIKUBYKUYUSRSM-UHFFFAOYSA-N 0.000 description 1
- KQTGCJMBUBYSLL-UHFFFAOYSA-N 4-piperidin-1-ylmorpholine Chemical compound C1CCCCN1N1CCOCC1 KQTGCJMBUBYSLL-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 229940127089 cytotoxic agent Drugs 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 230000007721 medicinal effect Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- UDGSVBYJWHOHNN-UHFFFAOYSA-N n',n'-diethylethane-1,2-diamine Chemical compound CCN(CC)CCN UDGSVBYJWHOHNN-UHFFFAOYSA-N 0.000 description 1
- DILRJUIACXKSQE-UHFFFAOYSA-N n',n'-dimethylethane-1,2-diamine Chemical compound CN(C)CCN DILRJUIACXKSQE-UHFFFAOYSA-N 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000012450 pharmaceutical intermediate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/52—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring condensed with a ring other than six-membered
Definitions
- This invention relates to compositions of matter, particularly to chemo-therapeutic organic compounds that are also of value as synthetic and pharmaceutical intermediates in preparing other chemo-therapeutic agents. More particularly the invention relates to compounds possessing bronchiodilatory, antispasmodic and local anesthetic properties in varying degrees.
- this invention relates to dialkylaminoalkyl imides of l,2-cis-cyclobutane dicarboxylic anhydride, their simple and quaternary salts.
- the novel compounds discovered are obtained by reacting the appropriate dialkylaminoalkylamine with the anhydride of 1,2-cis-cyclobutane dicarboxylic acid to form the intermediate amic acid which is cyclized to the imide by heating for 2 hours at 170 180 C.
- the imides are isolated directly from the re action mixture by vacuum distillation and are then converted to simple or quaternary salts by reaction with an acid or an alkyl halide respectively in suitable media.
- A- on R i) X- Formula 3
- A represents the azabicycloheptanedione nucleus
- n a number from 1 to 6
- R represents 2 alkyl groups with from 1 to 6 carbon atoms
- R an alkyl group with from 1 to 6 carbon atoms or an alkylene group containing 3 carbon atoms.
- X represents an anion, namely, chloride, iodide, bromide, acetate or sulfate.
- R may be the same as or different from R in any of the formulae given.
- Ionic chloride Calculated-l2.90%; found-13.l0%.
- N-DIALKYLAMINOALKYL-B-AZABICYCLO (3:210) HEPTANE 2,4-DIONES Analysts, Percent 13. P., N-substltutent 0. Mm Carbon Hydrogen Nltrogen Calcd. Found Oalcd. Found Calcd. Found diethylamlnobutyl. 104-108 0. 2 66. 63 66. 71 9. 59 0. 55 11.10 9. 98 dlethylarnlnoamyL. -114 0.1 67. 63 67. 55 9. 84 0. 72 10. 52 10. 64 dletbylarnlnohexyL -124 0. 1 6B. 53 68. 44 10. 06 10. 11 9. 99 10.
- the monomethi0dide (This was formed from the imide in acetone with a slight excess of methyl iodide, and was a white crystalline material, M. P. 236-238 C. decomposition. Recrystallized from isopropanol, M. P. 239.5241 C. decomposition.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Description
United States Patent DERIVATIVES 0F 3AZABICYCLO (322:0) HEPTANE-2,4-DIONE Charles H. Grogan, Falls Church, Va., and Leonard M. Rice, Baltimore, Md., assignors to The Geschlckter Fund for Medical Research, Inc., Washington, D. C., a corporation of New York No Drawing. Application October 10, 1955, Serial No. 539,653
11 Claims. (Cl. 260-2475) This invention relates to compositions of matter, particularly to chemo-therapeutic organic compounds that are also of value as synthetic and pharmaceutical intermediates in preparing other chemo-therapeutic agents. More particularly the invention relates to compounds possessing bronchiodilatory, antispasmodic and local anesthetic properties in varying degrees.
Specifically this invention relates to dialkylaminoalkyl imides of l,2-cis-cyclobutane dicarboxylic anhydride, their simple and quaternary salts.
It is a basic object of the present invention to provide novel organic compounds and methods for the prepara tion thereof.
It is another object of the invention to provide novel, physiologically active compounds characterized by chemotherapeutic or medicinal properties, particularly bronchiodilatory, antispasmodic and local anesthetic activity.
These and other objects and the manner in which they are accomplished will become apparent to those conversant with the art from the following description of the general class of compounds and certain specific examples of particular members thereof as well as general and specific methods of their preparation.
Generally stated, the novel compounds discovered are obtained by reacting the appropriate dialkylaminoalkylamine with the anhydride of 1,2-cis-cyclobutane dicarboxylic acid to form the intermediate amic acid which is cyclized to the imide by heating for 2 hours at 170 180 C. The imides are isolated directly from the re action mixture by vacuum distillation and are then converted to simple or quaternary salts by reaction with an acid or an alkyl halide respectively in suitable media.
0 n H H nc-co I (L N (CH2)..N=R ncc 11 HA 8 J Formulal Formula 2 The simple salts of these imides, formed on the side chain nitrogen are illustrated by Formula 2, and the Patented Aug. 6, 1957 monoquaternary salts, likewise formed on the side chain nitrogen are illustrated by Formula 3.
A- on =R i) X- Formula 3 In these formulae A represents the azabicycloheptanedione nucleus, n a number from 1 to 6, R represents 2 alkyl groups with from 1 to 6 carbon atoms, and R an alkyl group with from 1 to 6 carbon atoms or an alkylene group containing 3 carbon atoms. The structure (N=R) may represent a heterocyclic ring namely, morpholine, piperidine, pyrrolidine, piperazine or N- methyl piperazine. X represents an anion, namely, chloride, iodide, bromide, acetate or sulfate. In the quaternary salts R may be the same as or different from R in any of the formulae given.
The following examples of specific compounds and methods of their preparation will illustrate the manner in which they are obtained by the application of the general synthesizing procedure to particular members of the class of compounds discovered. It will be understood, however, that the following examples are merely illustrative and are not, nor are they intended to be, exhaustive of all the compounds embraced by this invention.
EXAMPLE I N dimethylaminoeihyl 3 azabicyclo(3:2:0)heptane- 2,4-dlone simple salts and quaternary salts The inside-0.2 mole of 1,2-cis-cyclobutane dicarboxylic anhydride was weighed into a 50 ml. 24/40 flask and 0.2 mole of dimethylaminoethylamine added rapidly in one lot. An exothermic reaction took place and the mass soon liquified. It was stirred until homogeneous (or heated if necessary to obtain a homogeneous liquid phase) and reweighed. Any amine lost (usually none) was replaced and a 12% excess of amine added. The reaction mixture was stirred until again homogeneous and heated slowly to l70-180 C. It was maintained at this temperature until water was no longer evolved (usually 2 hours) to cyclize the amic acid initially formed to the imide. Following the heating period, the flask was connected directly to a vacuum distillation apparatus and heated slowly to the boiling point so as to remove any lower boiling material such as unreacted amine. The material was distilled and the whole distilled between 1l4-116 C./l mm. It was redistilled and there was obtained 26.5 grams of imide, B. P. 86- 94 C./0.08 mm. as a clear, colorless, oily liquid, n =l.4938.
Carbon, H drogen, Nitrogen,
Percent ercent Percent Calculated 61. 20 8. 22 14. 28 Found E1. 32 8. 24 32 absolute ethanol increased the melting point to 259- 260 C.
Ionic iodide: Calculated-37.53%; found37.31%.
EXAMPLE II N diethylaminoethyl 3 azabicyclo(3:2:0)heptane- 2,4-dine simple and quaternary salts The imide.This imide was prepared ,in a manner analogous to that detailed under Example I by the re action of 0.2 mole of diethylaminoethylamine with 0.2 mole of the anhydride. On vacuum distillation 29 grams of a colorless oily liquid, B. P. 93-100" C./0.2 mm. was obtained, n =1.491O.
Nitrogen, Percent Carbon Percent Hydrogen, Percent N-dimethylaminopropyl-3-azabicyclo(3:2:0)heptane- 2,4-di0ne simple and quaternary salts The imide.--Reaction of 0.2 mole of dimethylamino- Calculated 8. Found 8.
pylamine with 0.1 mole of the anhydride as detailed under Example I yielded 16.6 grams of the title imide, B. P. 103 C./O.l mm., n "=1.49l8.
Carbon, Hydrogen, Nitrogen,
Percent Percent Percent Calculated E5. 51 9. 31 11. 76 Found 65. 63 9. 21 12.01
The monohydrochl0ride.-This was formed from the imide in isopropanol with an excess of alcoholic HCl and precipitation with ether, M. P. 149-151 C. not changed on recrystallization.
Ionic chloride: Calculated-l2.90%; found-13.l0%.
The m0n0methiodide.-This was formed from the imide in acetone with a slight excess of methyl iodide, M. P. 184-185 C. not changed on recrystallization.
Ionic iodide: Calculated-33.37%; found33.43%.
EXAMPLE V N-morpholinopropyl-3-azabicyclo(3:2.'0)heptane- 2,4-di0ne simple and quaternary salts The imide.This was formed by reaction of 0.1 mole of morpholinopropylamine with 0.1 mole of the anhydride as detailed under Example I. Obtained 21.1 grams, B. P. 150-155 C./0.3 mm., n =1.5130.
Carbon, Hydrogen, Nitrogen,
Percent Percent Percent Calculated 61. 88 7. 99 11. 10 Found 51. 97 7. 84 11. 32
N-DIALKYLAMINOALKYL-B-AZABICYCLO (3:210) HEPTANE 2,4-DIONES Analysts, Percent 13. P., N-substltutent 0. Mm Carbon Hydrogen Nltrogen Calcd. Found Oalcd. Found Calcd. Found diethylamlnobutyl. 104-108 0. 2 66. 63 66. 71 9. 59 0. 55 11.10 9. 98 dlethylarnlnoamyL. -114 0.1 67. 63 67. 55 9. 84 0. 72 10. 52 10. 64 dletbylarnlnohexyL -124 0. 1 6B. 53 68. 44 10. 06 10. 11 9. 99 10. 09 dlbutylamlnoethyl. 109-115 0. 2 6B. 53 6B. 38 11). [)6 9. 98 9. 99 10. 15 dihexylaminoethyl. -129 0. 1 71. 38 71. 31 10. 78 10. 67 8. 33 8. 5D morphollnoethyl 142-148 0. 2 60. 48 60. 62 7.61 7.68 11. TI} 11. B1 plperldlnoetbyl 138-144 0. 2 66. 07 65. 98 8. 53 8. 55 1 l. 86 11. 90
propylamine with 0.2 mole of the anhydride as detailed under Example I yielded 31 grams of the title imide, B. P. 87-97" C./0.2 mm., n =1.4942.
Carbon, Hydrogen, Nitrogen,
Percent Percent Percent Calculated 62. 83 8. 63 13. 32 Found 62. 75 B. 71 13. 22
EXAMPLE IV N-diethylaminopropyl-3-azabicyclo(3:2:0 heptane- 2,4-dz'0ne simple and quaternary salts The imide.--Reaction of 0.1 mole of diethylaminopro- The m0nohydrochl0ride.-This was formed from the imide in isopropanol with excess alcoholic-HG! and was a white crystalline material, M. P. 182-3 C. Recrystallized from isopropanol-ethyl ether, M. P. 185-186 C.
Ionic chloride: Calculated-12.28%; found-12.31%.
The monomethi0dide.-This was formed from the imide in acetone with a slight excess of methyl iodide, and was a white crystalline material, M. P. 236-238 C. decomposition. Recrystallized from isopropanol, M. P. 239.5241 C. decomposition.
Ionic iodide: Calculated-32.l9%; found-32.12%.
From the foregoing description of a novel class of compounds, details of preparation and characterization of exemplary members of the class, it will be understood that, on the basis of the discovery and knowledge dis closed herein, other specific compounds can be made and variations in the methods of synthesis resorted to. The appended table contains additional examples of imides prepared by the procedures detailed herein. Therefore, the specific compounds and methods disclosed herein are to be considered in all respects as illustrative and not restrictive, the scope of the discovery being indicated by the appended claims rather than the foregoing descriptive detailed examples, and all specific compounds and variations and methods which come within the meaning and range of equivalency of the claims are therefore intended to be embraced therein.
What is claimed and desired to be secured by United States Letters Patent is:
I. As a novel composition of matter, a compound selected from the group consisting of (1) compounds having the formula BIC-OH- where, in said formula, n is a number from 1 to 6, and R is selected from the group consisting of two alkyl groups with each alkyl group having from 1 to 6 carbon atoms and radicals which form, together with the nitrogen atom to which they are attached, a heterocyclic group selected from the group consisting of morpholino, piperidine and pyrrolidino, and (2) the acid addition salts and mono-quaternary salts of (l).
2. As a novel composition of matter, a mono-methonium salt of N-dimethylaminoethyl-3-azabicyclo(3:2:0)- heptane-2,4-dione.
3. As a novel composition of matter, a mono-metho- 6 nium salt of N-dimethylaminoethyl-3-azabicyclo(3:2:0)- heptane-2,4-dione.
4. As a novel composition of matter, a mono-methonium salt of N-dimethylaminopropyl-3-azabicyclo(3 :2:0)- heptane-2,4-dione.
5. As a novel composition of matter, a mono-methonium salt of N-diethylaminopropyl-3-azabicyclo(32:0)- heptane-2,4-dione.
6. As a novel composition of matter, a mono-methoniutn salt of N-morpholinopropyl-3-azabicyclo(3:2:0)- heptane-2,4-dione.
7. As a novel composition of matter, N-dimethylaminoethyl-3-azabicyclo( 3 :2 :0 heptane-2,4-dione.
8. As a novel composition of matter, the mono-methonium chloride of N-dimethylaminoethyl-3-azabicyclo- (3 :2:0)hpetane-2,4-dione.
9. As a novel composition of matter, N-diethylaminoethyl-3-azabicyclo(3 :2 0 heptane-2,4-dione.
10. As a novel composition of matter, the mono-methonium chloride of N diethylaminoethyl 3 azabicyclo- (3 :2 0)heptane-2,4-dione.
11. As a novel composition of matter, the mono-methonium chloride of N-dimethylamino-propyl-3-azabicyclo- (3 :2 0) heptane-2,4-dione.
References Cited in the file of this patent FOREIGN PATENTS 173,063 Great Britain Dec. 21, 1921
Claims (1)
1. AS A NOVEL COMPOSITION OF MATTER, A COMPOUND SELECTED FROM THE GROUP CONSISTING OF (1) COMPOUNDS HAVING THE FORMULA
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US539653A US2802004A (en) | 1955-10-10 | 1955-10-10 | Derivatives of 3-aza-bicyclo (3: 2: 0) heptane-2, 4-dione |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US539653A US2802004A (en) | 1955-10-10 | 1955-10-10 | Derivatives of 3-aza-bicyclo (3: 2: 0) heptane-2, 4-dione |
| CH813428X | 1955-10-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2802004A true US2802004A (en) | 1957-08-06 |
Family
ID=25738543
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US539653A Expired - Lifetime US2802004A (en) | 1955-10-10 | 1955-10-10 | Derivatives of 3-aza-bicyclo (3: 2: 0) heptane-2, 4-dione |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2802004A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2904548A (en) * | 1957-01-28 | 1959-09-15 | Geschickter Fund Med Res | N-substituted-3-azabicyclo [3:3:0] octane-2, 4-diones and salts thereof |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB173063A (en) * | 1920-09-21 | 1921-12-21 | Chem Ind Basel | Manufacture of soluble derivatives of camphoric acid |
-
1955
- 1955-10-10 US US539653A patent/US2802004A/en not_active Expired - Lifetime
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB173063A (en) * | 1920-09-21 | 1921-12-21 | Chem Ind Basel | Manufacture of soluble derivatives of camphoric acid |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2904548A (en) * | 1957-01-28 | 1959-09-15 | Geschickter Fund Med Res | N-substituted-3-azabicyclo [3:3:0] octane-2, 4-diones and salts thereof |
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