US3855276A - Phenanthryl ethylidene carbazic acid esters - Google Patents
Phenanthryl ethylidene carbazic acid esters Download PDFInfo
- Publication number
- US3855276A US3855276A US00425421A US42542173A US3855276A US 3855276 A US3855276 A US 3855276A US 00425421 A US00425421 A US 00425421A US 42542173 A US42542173 A US 42542173A US 3855276 A US3855276 A US 3855276A
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- US
- United States
- Prior art keywords
- phenanthryl
- ethylidene
- carbazic acid
- acid esters
- carbazic
- Prior art date
- 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 - Lifetime
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- -1 Phenanthryl ethylidene carbazic acid esters Chemical class 0.000 title claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 16
- 238000000034 method Methods 0.000 abstract description 6
- 238000002360 preparation method Methods 0.000 abstract description 6
- 230000002128 anti-rhinoviral effect Effects 0.000 abstract description 3
- 241000700605 Viruses Species 0.000 description 7
- 239000000203 mixture Substances 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 241000709661 Enterovirus Species 0.000 description 4
- 125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 description 4
- YIFJDVCSCBVZOC-UHFFFAOYSA-N (ethylideneamino)carbamic acid Chemical class CC=NNC(O)=O YIFJDVCSCBVZOC-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 229920001817 Agar Polymers 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 239000008272 agar Substances 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 239000003937 drug carrier Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000006187 pill Substances 0.000 description 3
- 230000001225 therapeutic effect Effects 0.000 description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 229920001800 Shellac Polymers 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000013553 cell monolayer Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 230000006378 damage Effects 0.000 description 2
- 230000003111 delayed effect Effects 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- 239000002702 enteric coating Substances 0.000 description 2
- 239000012055 enteric layer Substances 0.000 description 2
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000004208 shellac Substances 0.000 description 2
- ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 2
- 229940113147 shellac Drugs 0.000 description 2
- 235000013874 shellac Nutrition 0.000 description 2
- JKVNPRNAHRHQDD-UHFFFAOYSA-N 1-phenanthren-3-ylethanone Chemical compound C1=CC=C2C3=CC(C(=O)C)=CC=C3C=CC2=C1 JKVNPRNAHRHQDD-UHFFFAOYSA-N 0.000 description 1
- UUQHAAWMCLITRZ-KEOOTSPTSA-N 2-[(3S,6S,12S,20R,23S)-20-carbamoyl-12-[3-(diaminomethylideneamino)propyl]-3-(1H-indol-3-ylmethyl)-2,5,8,11,14,22-hexaoxo-17,18-dithia-1,4,7,10,13,21-hexazabicyclo[21.3.0]hexacosan-6-yl]acetic acid Chemical compound N1C(=O)[C@H](CC(O)=O)NC(=O)CNC(=O)[C@H](CCCN=C(N)N)NC(=O)CCSSC[C@@H](C(N)=O)NC(=O)[C@@H]2CCCN2C(=O)[C@@H]1CC1=CNC2=CC=CC=C12 UUQHAAWMCLITRZ-KEOOTSPTSA-N 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- 235000019739 Dicalciumphosphate Nutrition 0.000 description 1
- 229920002491 Diethylaminoethyl-dextran Polymers 0.000 description 1
- 229910004373 HOAc Inorganic materials 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
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- 241000709664 Picornaviridae Species 0.000 description 1
- QOSMNYMQXIVWKY-UHFFFAOYSA-N Propyl levulinate Chemical compound CCCOC(=O)CCC(C)=O QOSMNYMQXIVWKY-UHFFFAOYSA-N 0.000 description 1
- 235000021355 Stearic acid Nutrition 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
- 229930006000 Sucrose Natural products 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 229940081735 acetylcellulose Drugs 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000003708 ampul Substances 0.000 description 1
- 230000000840 anti-viral effect Effects 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 229960000541 cetyl alcohol Drugs 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 239000003240 coconut oil Substances 0.000 description 1
- 235000019864 coconut oil Nutrition 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 239000002385 cottonseed oil Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000000120 cytopathologic effect Effects 0.000 description 1
- NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 1
- 229940038472 dicalcium phosphate Drugs 0.000 description 1
- 229910000390 dicalcium phosphate Inorganic materials 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 210000001198 duodenum Anatomy 0.000 description 1
- 239000008157 edible vegetable oil Substances 0.000 description 1
- 238000009505 enteric coating Methods 0.000 description 1
- 239000012894 fetal calf serum Substances 0.000 description 1
- 239000012054 flavored emulsion Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- WFJRIDQGVSJLLH-UHFFFAOYSA-N methyl n-aminocarbamate Chemical compound COC(=O)NN WFJRIDQGVSJLLH-UHFFFAOYSA-N 0.000 description 1
- 239000007758 minimum essential medium Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000006186 oral dosage form Substances 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 239000008024 pharmaceutical diluent Substances 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 230000000241 respiratory effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 235000012431 wafers Nutrition 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C281/00—Derivatives of carbonic acid containing functional groups covered by groups C07C269/00 - C07C279/00 in which at least one nitrogen atom of these functional groups is further bound to another nitrogen atom not being part of a nitro or nitroso group
- C07C281/02—Compounds containing any of the groups, e.g. carbazates
Definitions
- this invention relates to compounds of the formula:
- the compounds of the present invention exhibit antiviral activity against a variety of rhinoviruses.
- Confluent monolayers of a continuous cell-line such as I-IeLa, HEp-Z, KB or L-l32 grown in plastic tissue culture dishes were infected with one of the viruses causing respiratory illness such as the common cole.
- viruses include members of the picornavirus group including the rhinoviruses, for example, types 1B, 2, 5, 14, or 23 and including the enteroviruses, for example, Coxsackie A-l5 or A-2l.
- the agar medium used for this purpose was of the following formulation:
- the virus-infected cell monolayers plus test compound were incubated for 3 to 5 days in a humidified atmosphere of 5 percent carbon dioxide at either 33 or 37C., depending on the virus. The ability of these compounds to protect tissues from destruction by the viruses was then evident after staining the residual, uninfected cells with 0.5 percent crystal violet in 20 percent ethanol.
- 3-[ l-( 3-phenanthryl)ethylidene carbazic acid ethyl ester is also active in providing protection against Coxsackie A-2l virus.
- the active components of this invention can be used in compositions such as tablets: the principal active ingredient is mixed with conventional tableting ingredients such as corn starch, lactose, sucrose, sorbitol,,talc, stearic acid, magnesium stearate, dicalcium phosphate, gums, or similar materials as non-toxic pharmaceutically acceptable diluents or carriers.
- the tablets or pills of the novel compositions can be laminated or otherwise compounded to provide a dosage form affording the advantage of prolonged or delayed action or predetermined successive action of the enclosed medication.
- the tablet or pill can comprise an inner dosage and an outer dosage component, the latter being in the form of an envelope over the former.
- the two components can be separated by an enteric layer which serves to resist disintegration in the stomach and permits the inner component to pass intact into the duodenum or to be delayed in release.
- enteric layers or coatings such materials including a number of polymeric acids or mixtures of polymeric acids with such materials as shellac, shellac and cetyl alcohol, cellulose acetate and the like.
- enteric coating comprises a styrene-maleic acid copolymer together with known materials contributing to the enteric properties of the coating.
- liquid forms in which the novel compositions of the present invention may be incoporated for administration include suitably flavored emulsions with edible oils, such as, cottonseed oil, sesame oil, coconut oil, peanut oil, and the like, as well as elixirs and similar pharmaceutical vehicles.
- edible oils such as, cottonseed oil, sesame oil, coconut oil, peanut oil, and the like
- elixirs and similar pharmaceutical vehicles such as, elixirs and similar pharmaceutical vehicles.
- Sterile suspensions or solutions can be prepared for parenteral use. isotonic preparations containing suitable preservatives are also de- 5.92; N, 9.15. Found: C, 74.59; H, 5.91; N, 9.11.
- EXAMPLE 2 Preparation of warmblooded animal subjects, each unit containing a 5 3-[ l-(3-Phenanthryl)ethylidene]-carbazic acid methyl predetermined quantity of active component calculated to produce the desired therapeutic effect in association with the required pharmaceutical diluent, carrier or vehicle.
- the specification for the novel dosage forms of this invention are indicated by characteristics of the active component and the particular therapeutic effect to be achieved or the limitations inherent in the art of compounding such an active component for therapeutic use in warm-blooded animals as disclosed in this specification.
- suitable oral dosage forms in accord with this invention are tablets, capsules, pills, powder packets, granules, wafers, cachets, teaspoonfuls, dropperfuls, ampules, vials, segregated multiples of any of the foregoing and other forms as herein described.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The preparation of the phenanthryl ethylidene carbazic acid alkyl esters having antirhinoviral activity and method of use are described.
Description
I United States Patent [191 Dusza et al.
[ Dec. 17, 1974 PHENANTHRYL ETHYLIDENE CARBAZIC ACID ESTERS [75] Inventors: John Paul Dusza, Nanuet; Harry Lee Lindsay, Pearl River; Seymour Bernstein, New City, all of NY.
'[73] Assignee: American Cyanamid Company,
Stamford, Conn.
[22] Filed: Dec. 17, 1973 [21] App]. No.: 425,421
[52] U.S. Cl. 260/471 C, 424/300 [51] Int. Cl. C07c 125/06 [58] Field of Search 260/471 C Primary Examiner-James A. Patten Assistant Examiner-L. A. Thaxton Attorney, Agent, or Firm-Ernest Y. Miller [5 7] ABSTRACT The preparation of the phenanthryl ethylidene carbazic acid alkyl esters having antirhinoviral activity and method of use are described.
3 Claims, No Drawings PHENANTI-IRYL ETHYLIDENE CARBAZIC ACID ESTERS DESCRIPTION OF THE INVENTION This invention is concerned with phenanthryl ethyli- 5 dene carbazic acid alkyl esters and method of using the same.
In particular, this invention relates to compounds of the formula:
I C=NNHCCOR Wherein R is lower alkyl C, to C The compounds of the present invention are prepared by methods which can be graphically illustrated as follows:
'+ NH NHc'ooR 40 n [HClg/or gl. HOAc E ano 1-? Hrs. Reflux =NNHCOOR Wherein R is a lower alkyl, C to C Among the specific compounds which can be prepared by the above method,are, for example: 3-[ l-(3- phenanthryl)ethylidene]-carbazic acid-ethyl ester, 3- l-(3-phenanthryl)ethylidenelcarbazic acid methyl ester, 3-[l-(3-phenanthryl)ethylidene1-carbazic acid propyl ester, 3-[ l-(3-phenanthryl)ethylidenel-carbazic acid t-butyl ester. 3-[ l-(3-phenanthryl)ethylidenelcarbazic acid hexyl ester.
The compounds of the present invention exhibit antiviral activity against a variety of rhinoviruses.
The following procedure is used to determine the anti-rhinoviral activity of the present compounds. Confluent monolayers of a continuous cell-line such as I-IeLa, HEp-Z, KB or L-l32 grown in plastic tissue culture dishes were infected with one of the viruses causing respiratory illness such as the common cole. These viruses include members of the picornavirus group including the rhinoviruses, for example, types 1B, 2, 5, 14, or 23 and including the enteroviruses, for example, Coxsackie A-l5 or A-2l. Protection of the tissues to the cytopathic effects of the viruses was ascertained by means of a plaque inhibition test in which the test compound was adsorbed into a filter paper disc and placed on the agar used to overlay the infected cell monolayers, or by incorporation into the said agar overlay. The agar medium used for this purpose was of the following formulation:
Minimum Essential Medium (Eagles) containing Earles Salts (Grand Island Biological Company, Grand Island, NY.) and to which has been added:
The virus-infected cell monolayers plus test compound were incubated for 3 to 5 days in a humidified atmosphere of 5 percent carbon dioxide at either 33 or 37C., depending on the virus. The ability of these compounds to protect tissues from destruction by the viruses was then evident after staining the residual, uninfected cells with 0.5 percent crystal violet in 20 percent ethanol.
A summary of the test results obtained on representative compounds are shown in Table I.
In addition, 3-[ l-( 3-phenanthryl)ethylidene carbazic acid ethyl ester is also active in providing protection against Coxsackie A-2l virus.
The active components of this invention can be used in compositions such as tablets: the principal active ingredient is mixed with conventional tableting ingredients such as corn starch, lactose, sucrose, sorbitol,,talc, stearic acid, magnesium stearate, dicalcium phosphate, gums, or similar materials as non-toxic pharmaceutically acceptable diluents or carriers. The tablets or pills of the novel compositions can be laminated or otherwise compounded to provide a dosage form affording the advantage of prolonged or delayed action or predetermined successive action of the enclosed medication. For example, the tablet or pill can comprise an inner dosage and an outer dosage component, the latter being in the form of an envelope over the former. The two components can be separated by an enteric layer which serves to resist disintegration in the stomach and permits the inner component to pass intact into the duodenum or to be delayed in release. A variety of materials can be used for such enteric layers or coatings, such materials including a number of polymeric acids or mixtures of polymeric acids with such materials as shellac, shellac and cetyl alcohol, cellulose acetate and the like. A particularly advantageous enteric coating comprises a styrene-maleic acid copolymer together with known materials contributing to the enteric properties of the coating.
The liquid forms in which the novel compositions of the present invention may be incoporated for administration include suitably flavored emulsions with edible oils, such as, cottonseed oil, sesame oil, coconut oil, peanut oil, and the like, as well as elixirs and similar pharmaceutical vehicles. Sterile suspensions or solutions can be prepared for parenteral use. isotonic preparations containing suitable preservatives are also de- 5.92; N, 9.15. Found: C, 74.59; H, 5.91; N, 9.11.
EXAMPLE 2 Preparation of warmblooded animal subjects, each unit containing a 5 3-[ l-(3-Phenanthryl)ethylidene]-carbazic acid methyl predetermined quantity of active component calculated to produce the desired therapeutic effect in association with the required pharmaceutical diluent, carrier or vehicle. The specification for the novel dosage forms of this invention are indicated by characteristics of the active component and the particular therapeutic effect to be achieved or the limitations inherent in the art of compounding such an active component for therapeutic use in warm-blooded animals as disclosed in this specification. Examples of suitable oral dosage forms in accord with this invention are tablets, capsules, pills, powder packets, granules, wafers, cachets, teaspoonfuls, dropperfuls, ampules, vials, segregated multiples of any of the foregoing and other forms as herein described.
DETAILED DESCRIPTION The following examples describe in detail the preparation of representative compounds of this invention.
EXAMPLE 1 Preparation of 3-[ l-(3-Phenanthryl)ethylidene1-carbazic acid ethyl ester ester A mixture of l 1.0 gm. of 3-acetylphenanthrene and 9.0 gm. of methyl carbazate in 50 ml. of a solution of 4 percent glacial acetic acid in absolute ethanol is refluxed for 2 hours and then cooled in a refrigerator. The precipitate is washed with percent ethanol and then water. The precipitate is dissolved in methylene chloride and passed through an acid silicate of magnesium column. The refluxing effluent is treated with hexane to crystallization. The product is collected and dried, yielding 12.1 gm., melting point l76-l78.5C. Anal. Calcd. for c,,,H,,N,o,: C, 73.95; H, 5.52; N. 9.58. Found: C, 74.05; H, 5.57; N, 9.55.
We claim:
1. A compound of the formula:
C=N -NacooR wherein R is lower alkyl C, to C 2. The compound in accordance with claim 1, 3-[1- (3-phenanthryl)ethylidenel-carbazic acid ethyl ester. 3. The compound in accordance with claim 1, 3-[1- (3-phenanthry1)ethylidene]-carbazic acid methyl ester.
UNITED sTATEs PATENT OFFICE CERTIFICATE OF CORRECTIN PatentNo. 5,855,276 Dated December 17, 197
John Paul Dusza Harry Lee Lindsay and Inventor(s) Seymour Bernstein It is certified that error appears in the above-identified patent and that said'Letters Patent are hereby corrected as shown below:
, Column 2, between lines 21 and 22, please insert the following:
- Ionagar No. 2 0.4%
Diethylaminoethyl dextran 0.01% Magnesium chloride 0.06% Fetal calf serum 2% (v/v) Column 2, between lines 51 and 32, please insert th following table;
TABLE I Rhinovirus 3-[1- 3Phenanthryl)ethylidene carbazic acid ethyl ester 3-[l-(3-Phenanthryl)ethylidene]- carbazic acid methyl ester Protects tissue from destruction by virus Signed and sealed this 8th day of April 1975.
(SEAL) Attest:
C. I-ARSHALL DANN RUTH C. I-IASON Commissioner of Patents Attesting Officer. and Trademarks USCOMM-DC G037 B-PSD I ORM PO-iOSO (10-69) v (LS. GOVERNMENT PRINTING OFFICE 1 I", 0-3384
Claims (3)
1. A COMPOUND OF THE FORMULA
2. The compound in accordance with claim 1, 3-(1-(3-phenanthryl)ethylidene)-carbazic acid ethyl ester.
3. The compound in accordance with claim 1, 3-(1-(3-phenanthryl)ethylidene)-carbazic acid methyl ester.
Priority Applications (15)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US00425421A US3855276A (en) | 1973-12-17 | 1973-12-17 | Phenanthryl ethylidene carbazic acid esters |
| IL46086A IL46086A0 (en) | 1973-12-17 | 1974-11-20 | Alkylidene carbazic acid esters |
| PH16553A PH10280A (en) | 1973-12-17 | 1974-11-22 | Phenanthryl ethylidene carbazic esters |
| DE19742455684 DE2455684A1 (en) | 1973-12-17 | 1974-11-25 | SUBSTITUTED CARBAZIC ACID ALKYLESTERS AND THE METHOD FOR THEIR PRODUCTION |
| AU75849/74A AU7584974A (en) | 1973-12-17 | 1974-11-28 | Substituted carbazic acid alkyl esters |
| AR256716A AR203665A1 (en) | 1973-12-17 | 1974-11-28 | METHOD FOR PREPARING ETHYLESTERS OF 3-SUBSTITUTED CARBACIC ACID |
| NL7415989A NL7415989A (en) | 1973-12-17 | 1974-12-09 | Antirhinoviral benzofuranyl ethylidene carbazic acid esters - prepd. from (substd.) 2-acetylbenzofuran and alkyl carbazate ester |
| DK648774A DK648774A (en) | 1973-12-17 | 1974-12-12 | |
| FI3584/74A FI358474A7 (en) | 1973-12-17 | 1974-12-12 | |
| NO744537A NO744537L (en) | 1973-12-17 | 1974-12-16 | |
| SE7415800A SE7415800L (en) | 1973-12-17 | 1974-12-16 | |
| DD183064A DD118419A5 (en) | 1973-12-17 | 1974-12-16 | |
| RO7480806A RO71805A (en) | 1973-12-17 | 1974-12-16 | PROCESS FOR THE PREPARATION OF CARBASIC ACID ALCOHOL ESTERS |
| JP49144165A JPS50116448A (en) | 1973-12-17 | 1974-12-17 | |
| FR7441577A FR2254328A1 (en) | 1973-12-17 | 1974-12-17 | Antirhinoviral benzofuranyl ethylidene carbazic acid esters - prepd. from (substd.) 2-acetylbenzofuran and alkyl carbazate ester |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US00425421A US3855276A (en) | 1973-12-17 | 1973-12-17 | Phenanthryl ethylidene carbazic acid esters |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3855276A true US3855276A (en) | 1974-12-17 |
Family
ID=23686501
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US00425421A Expired - Lifetime US3855276A (en) | 1973-12-17 | 1973-12-17 | Phenanthryl ethylidene carbazic acid esters |
Country Status (2)
| Country | Link |
|---|---|
| US (1) | US3855276A (en) |
| PH (1) | PH10280A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2446285A1 (en) * | 1978-09-05 | 1980-08-08 | American Cyanamid Co | Bis:hydrazone derivs. of anthracene 9,10-di:carbonyl cpds. - useful as antibacterials and antitumour agents |
| US4570002A (en) * | 1982-05-04 | 1986-02-11 | Egyt Gyogyszervegyeszeti Gyar | Carbazic acid derivatives |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3560503A (en) * | 1968-09-18 | 1971-02-02 | Council Scient Ind Res | Di-lower alkyl-substituted octahydropyrazinopyrimidinones |
-
1973
- 1973-12-17 US US00425421A patent/US3855276A/en not_active Expired - Lifetime
-
1974
- 1974-11-22 PH PH16553A patent/PH10280A/en unknown
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3560503A (en) * | 1968-09-18 | 1971-02-02 | Council Scient Ind Res | Di-lower alkyl-substituted octahydropyrazinopyrimidinones |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2446285A1 (en) * | 1978-09-05 | 1980-08-08 | American Cyanamid Co | Bis:hydrazone derivs. of anthracene 9,10-di:carbonyl cpds. - useful as antibacterials and antitumour agents |
| US4570002A (en) * | 1982-05-04 | 1986-02-11 | Egyt Gyogyszervegyeszeti Gyar | Carbazic acid derivatives |
Also Published As
| Publication number | Publication date |
|---|---|
| PH10280A (en) | 1976-11-05 |
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