NZ260896A - Use of 2-[4-[bis(4-fluorophenyl)methylene]-1-piperidinyl]ethyl substituted thiazolopyrimidinone and -pyridopyrimidinone derivatives for preparing medicaments for treating addiction - Google Patents
Use of 2-[4-[bis(4-fluorophenyl)methylene]-1-piperidinyl]ethyl substituted thiazolopyrimidinone and -pyridopyrimidinone derivatives for preparing medicaments for treating addictionInfo
- Publication number
- NZ260896A NZ260896A NZ260896A NZ26089691A NZ260896A NZ 260896 A NZ260896 A NZ 260896A NZ 260896 A NZ260896 A NZ 260896A NZ 26089691 A NZ26089691 A NZ 26089691A NZ 260896 A NZ260896 A NZ 260896A
- Authority
- NZ
- New Zealand
- Prior art keywords
- habit
- drugs
- addiction
- forming
- alcohol
- Prior art date
Links
- 239000003814 drug Substances 0.000 title claims description 45
- 206010012335 Dependence Diseases 0.000 title claims description 20
- -1 2-[4-[bis(4-fluorophenyl)methylene]-1-piperidinyl]ethyl Chemical group 0.000 title description 4
- AKDQOJPOLRMVMF-UHFFFAOYSA-N [1,3]thiazolo[5,4-d]pyrimidine 3-oxide Chemical class N1=CN=C2S(=O)C=NC2=C1 AKDQOJPOLRMVMF-UHFFFAOYSA-N 0.000 title 1
- 229940079593 drug Drugs 0.000 claims description 41
- ZPUCINDJVBIVPJ-LJISPDSOSA-N cocaine Chemical compound O([C@H]1C[C@@H]2CC[C@@H](N2C)[C@H]1C(=O)OC)C(=O)C1=CC=CC=C1 ZPUCINDJVBIVPJ-LJISPDSOSA-N 0.000 claims description 30
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 16
- 229960003920 cocaine Drugs 0.000 claims description 15
- 150000001875 compounds Chemical class 0.000 claims description 15
- 229960002428 fentanyl Drugs 0.000 claims description 11
- PJMPHNIQZUBGLI-UHFFFAOYSA-N fentanyl Chemical compound C=1C=CC=CC=1N(C(=O)CC)C(CC1)CCN1CCC1=CC=CC=C1 PJMPHNIQZUBGLI-UHFFFAOYSA-N 0.000 claims description 11
- 208000024891 symptom Diseases 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 3
- JUQLTPCYUFPYKE-UHFFFAOYSA-N ritanserin Chemical compound CC=1N=C2SC=CN2C(=O)C=1CCN(CC1)CCC1=C(C=1C=CC(F)=CC=1)C1=CC=C(F)C=C1 JUQLTPCYUFPYKE-UHFFFAOYSA-N 0.000 description 16
- 229950009626 ritanserin Drugs 0.000 description 15
- 239000003795 chemical substances by application Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 239000004480 active ingredient Substances 0.000 description 4
- 230000037396 body weight Effects 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 206010063659 Aversion Diseases 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 239000012530 fluid Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000012453 solvate Substances 0.000 description 3
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 description 2
- 244000025254 Cannabis sativa Species 0.000 description 2
- 235000012766 Cannabis sativa ssp. sativa var. sativa Nutrition 0.000 description 2
- 235000012765 Cannabis sativa ssp. sativa var. spontanea Nutrition 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 208000029650 alcohol withdrawal Diseases 0.000 description 2
- 230000035622 drinking Effects 0.000 description 2
- 239000003937 drug carrier Substances 0.000 description 2
- 239000000380 hallucinogen Substances 0.000 description 2
- 229960002715 nicotine Drugs 0.000 description 2
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 description 2
- 229940127240 opiate Drugs 0.000 description 2
- WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000003204 tranquilizing agent Substances 0.000 description 2
- 230000002936 tranquilizing effect Effects 0.000 description 2
- DNCYBUMDUBHIJZ-UHFFFAOYSA-N 1h-pyrimidin-6-one Chemical compound O=C1C=CN=CN1 DNCYBUMDUBHIJZ-UHFFFAOYSA-N 0.000 description 1
- ZGUPMFYFHHSNFK-UHFFFAOYSA-N 3-[2-[4-[bis(4-fluorophenyl)methylidene]piperidin-1-yl]ethyl]-2-methylpyrido[1,2-a]pyrimidin-4-one Chemical compound CC=1N=C2C=CC=CN2C(=O)C=1CCN(CC1)CCC1=C(C=1C=CC(F)=CC=1)C1=CC=C(F)C=C1 ZGUPMFYFHHSNFK-UHFFFAOYSA-N 0.000 description 1
- 208000019901 Anxiety disease Diseases 0.000 description 1
- COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
- 208000004547 Hallucinations Diseases 0.000 description 1
- 239000004866 Hashish Substances 0.000 description 1
- 206010019233 Headaches Diseases 0.000 description 1
- IDBPHNDTYPBSNI-UHFFFAOYSA-N N-(1-(2-(4-Ethyl-5-oxo-2-tetrazolin-1-yl)ethyl)-4-(methoxymethyl)-4-piperidyl)propionanilide Chemical group C1CN(CCN2C(N(CC)N=N2)=O)CCC1(COC)N(C(=O)CC)C1=CC=CC=C1 IDBPHNDTYPBSNI-UHFFFAOYSA-N 0.000 description 1
- 206010028813 Nausea Diseases 0.000 description 1
- 241000208125 Nicotiana Species 0.000 description 1
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 239000008896 Opium Substances 0.000 description 1
- 206010044565 Tremor Diseases 0.000 description 1
- 206010047700 Vomiting Diseases 0.000 description 1
- 235000013334 alcoholic beverage Nutrition 0.000 description 1
- 229960001391 alfentanil Drugs 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 230000036506 anxiety Effects 0.000 description 1
- 229940125717 barbiturate Drugs 0.000 description 1
- 229940049706 benzodiazepine Drugs 0.000 description 1
- 150000001557 benzodiazepines Chemical class 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- ANTSCNMPPGJYLG-UHFFFAOYSA-N chlordiazepoxide Chemical compound O=N=1CC(NC)=NC2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 ANTSCNMPPGJYLG-UHFFFAOYSA-N 0.000 description 1
- HCAJEUSONLESMK-UHFFFAOYSA-N cyclohexylsulfamic acid Chemical compound OS(=O)(=O)NC1CCCCC1 HCAJEUSONLESMK-UHFFFAOYSA-N 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- AAOVKJBEBIDNHE-UHFFFAOYSA-N diazepam Chemical compound N=1CC(=O)N(C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 AAOVKJBEBIDNHE-UHFFFAOYSA-N 0.000 description 1
- RUZYUOTYCVRMRZ-UHFFFAOYSA-N doxazosin Chemical compound C1OC2=CC=CC=C2OC1C(=O)N(CC1)CCN1C1=NC(N)=C(C=C(C(OC)=C2)OC)C2=N1 RUZYUOTYCVRMRZ-UHFFFAOYSA-N 0.000 description 1
- 206010013663 drug dependence Diseases 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000005059 halophenyl group Chemical group 0.000 description 1
- 231100000869 headache Toxicity 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 230000002452 interceptive effect Effects 0.000 description 1
- 230000003340 mental effect Effects 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000004081 narcotic agent Substances 0.000 description 1
- 230000008693 nausea Effects 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 229960001027 opium Drugs 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 229960001412 pentobarbital Drugs 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 230000035790 physiological processes and functions Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000003236 psychic effect Effects 0.000 description 1
- 229950010947 seganserin Drugs 0.000 description 1
- 208000011117 substance-related disease Diseases 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000009897 systematic effect Effects 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 229940072690 valium Drugs 0.000 description 1
- 230000008673 vomiting Effects 0.000 description 1
- 230000036642 wellbeing Effects 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
New Zealand Paient Spedficaiion for Paient Number £60896 2 6 r; P Priority Date(s): 1.*L'.&./.SQ., ;{mass: •&....K&1&UISQ& ;^uWldtikm Da^o:....?..^...^.y.L..!.?.?Z. r .O. Journal No: i&H5£ ;NO DRAWINGS ;IMMtor tto pfOMiskms vi to&g+ ;Won 23 (1) the ;CctanigfeAfc..:. ;Specification Ms b#an anH d>f>< ;* i» .'Si. intfftfe i O J UN 1934 Patents Form No. 5 PATENTS ACT 1953 COMPLETE SPECIFICATION AGENTS FOR TREATING ADDICTION TO HABIT-FORMING DRUGS We, JANSSEN PHARMACEUTICS NV, of Turnhoutseweg 30, B2340-Beerse, Belgium, Belgian company do hereby declare this invention to be described in the following statement: -la- 2,6 C JAB 751-FF It is generally known that the repeated consumption of habit-forming drugs such as alcohol, minor tranquilizers, stimulantia, opiates, hallucinogens, nicotine in many instances leads to different degrees of addiction. Typically, such addiction is characterized by a need or desire to continue the use of the drug and to obtain it, not 15 seldom by all means, and further by a tendency to increase its dosage. This usually results in a psychological and usually a physiological dependence on the effects of such drugs and eventually has a detrimental effect on the addicted individual and on society.
Once a certain degree of addiction is reached, abstention of habit-forming drugs becomes a serious problem and is often accompanied by undesirable physical and/or 20 psychic symptoms. Therefore, an agent decreasing or overcoming such addiction and, if possible, alleviating or removing the symptoms related to the withdrawal of such habit-forming drugs would be highly welcomed, not only by drug addicts, but also by society in general.
It now has been found that certain 4-[bis(halophenyl)methylene]-l-piperidinyl derivatives alleviate, supress or overcome addiction to habit-forming drugs and further, once an individual reaches a certain state of addiction, decrease or even remove symptoms related to withdrawal of habit-forming drugs.
The present invention therefore is concerned with agents for treating individuals suffering from addiction to habit-forming drugs, said agents being compounds of formula yCH3 ~~ a), (CH2)2-N -2- 9 £ U V or the pharmaceutically acceptable acid addition salts thereof, wherein A represents -CH=CH- or -S-. In another aspect, the present invention concerns agents for treating individuals addicted to habit-forming drugs, suffering from symptoms related to the withdrawal or abstention of such drugs, which agents are compounds of formula (I) as 5 defined above.
The compound of formula (I) wherein A is -S-, namely 6-[2-[4-[bis(4-fluorophenyl)-methylene]-l-piperidinyl]ethyl]-7-methyl-5H-thiazolo[3,2-a]pyrimidin-5-one is genericaily designated as ritanserin. The compound of formula (I) wherein A is 10 -CH=CH-, namely 3-[2-[4-[bis(4-fluorophenylmethylene]-l-piperidinyl]ethyl]-2- methyl-4H-pyrido[l,2-a]pyrimidin-4-one is genericaily designated as seganserin. These compounds as well as their preparation and pharmacological properties are known from US-4,485,107.
The aforementioned term "pharmaceutically acceptable acid addition salt" is meant to comprise those salts obtained by treating the base form of the active ingredients of formula (I) with appropriate acids, such as, for example, inorganic acids, e.g. hydrochloric, hydrobromic and the like acids, sulfuric acid, nitric acid, phosphoric acid and the like; or organic acids, such as, for example, acetic, propanoic, hydroxyacetic, 20 2-hydroxypropanoic, 2-oxopropanoic, ethanedioic, propanedioic, butanedioic, (Z)-2-butenedioic, (E)-2-butenedioic, 2-hydroxybutanedioic, 2,3-dihydroxybutanedioic, 2-hydroxy-l!2,3-propanetricarboxylic, methanesulfonic, ethanesulfonic, benzene-sulfonic, 4-methylbenzenesulfonic, cyclohexanesulfamic, 2-hydroxybenzoic, 4-amino-2-hydroxybenzoic and the like acids. The term "pharmaceutically acceptable acid 25 addition salt" also comprises the solvates which the compounds of formula (I) may form and said solvates are intended to be included within the scope of the present invention. Examples of such solvates are e.g. the hydrates, alcoholates and the like.
Habit-forming drugs as referred hereinabove comprise various agents such as alcohol; 30 minor tranquilizers such as barbiturates, e.g. pentobarbital, and benzodiazepines, e.g. librium, valium; stimulantia, e.g. cocaine, amphetamines and nicotine; opiates such as fentanyl, alfentanyl and heroine; and hallucinogens, such as LSD; either in pure form or in admixture. Further are comprised products of various kind containing the aforementioned agents such as, for example, the various alcoholic beverages, tobacco, 35 opium, hashish, marijuana and the like. Certain of the aforementioned habit-forming drugs are also referred to as drugs of abuse (or simply as "drugs") or as narcotics. ? has An individual condnuously using these habit-forming drugs usually becomes addicted thereto. In some cases, addiction arises even after having taken the drug only a few times. Individuals being addicted to habit-forming drugs are confronted with a need, desire or longing for such drugs, the strength thereof depending on the individual, the I degree of addiction or the kind of drug. In some instances, this need, desire or longing is accompanied by (or causes) a neglecting of the addicted individual's well-being and health, e.g. a loss of apetite, a reduction of mental awareness, social disbehavior and the like. The latter factors too are to be considered as undesired side effects of drug addiction which can be treated by the agents of the present invention.
Individuals thus having become addicted and wanting, or being necessitated, to discontinue the use of habit-forming drugs usually find themselves confronted with a number of undesired symptoms. As symptoms accompanying withdrawal or abstention of habit-forming drugs there may be mentioned a general feeling of discomfort, headache, tremor, anxiety, hallucinations, nausea, vomiting and the like, and in 15 particular a continuous desire or longing for the habit-forming drug having caused the addiction.
The compounds of formula (I) and their acid addition salts are preferably administered formulated in usual pharmaceutical compositions comprising an effective amount of the 20 active ingredient and a suitable pharmaceutically acceptable carrier. Depending on the mode of administration, such compositions may take a variety of forms, e.g. tablets, solutions for parenteral administration, capsules, solutions or suspensions for oral intake, powders and the like. Such compositions are prepared by intimately mixing the active ingredient with one or more suitable carriers and converting this mixture into a 25 form suitable for administration.
Hence, the present invention also concerns compositions as mentioned above, containing a pharmaceutically acceptable carrier and an effective amount of the afore-defined compound of formula (I) as active ingredient, for alleviating, suppressing or overcoming addiction to habit-forming drugs, or for treating individuals addicted to 30 habit-forming drugs suffering from symptoms related to the withdrawal or abstention of said drugs.
In still a further aspect, the present invention is concerned with a method of treating individuals suffering from addiction to habit-forming drugs, said method comprising the administration to said individuals of a compound of formula (I) as defined above, or a 35 pharmaceutically acceptable acid addition salt thereof, in an amount effective in alleviating, suppressing or overcoming said addiction. -4- L U u V.i" The present invention also concerns a method of treating individuals addicted to habit-forming drugs, suffering from symptoms related to the withdrawal or abstention of such drugs, which comprises administering to said persons a compound of formula (I) or an acid-addition salt thereof, in an amount effective in alleviating or overcoming said 5 symptoms.
The dose to be administered may vary upon the individual which is treated, and is dependent on his or her body size, the degree of addiction and in particular on the kind | oi habit-forming drug causing the addiction.
A suitable daily dose is contemplated to vary between about 0.1 mg/kg and 50 mg/kg 10 body weight, and in particular between 0.5 and 10 mg/kg body weight, more in particular between 0.5 and 5 mg/kg body weight.
In still a further aspect of the present invention there is provided the use of a compound of formula (I) as defined above for the manufacture of a medicament for 15 alleviating, suppressing or overcoming addiction to habit-forming drugs, or for treating individuals addicted to habit-forming drugs suffering from symptoms related to the withdrawal or abstention of said drugs.
The effectiveness of the compounds of formula (I), as defined above, in overcoming 20 addiction to habit-forming drugs can be demonstrated in the following test procedures.
Example 1 Rats forced to drink 3% alcohol for a week followed by a week of alcohol withdrawal, reveal a high preference for alcohol when given the choice between 3% .25 alcohol and water.
The compound ritanserin, given during both the period of alcohol withdrawal and choice between alcohol and water, results in a dose-related reduction in the preference for alcohol. Doses > 0.63 mg/kg body weight ritanserin given subcutaneoulsy once a day, reduced total alcohol consumption as well as the relative preference for alcohol. At 30 10 mg/kg ritanserin, the highest dose tested, alcohol consumption was reduced with 58% and none of the tested animals had a pronounced preference for alcohol anymore. Simultaneous with the reduction in alcohol consumption, there was an increased water intake, keeping total fluid intake constant. Ritanserin's activity was observed from the first day of choice and the drug remained active during all five test days.
These results indicate that ritanserin cir. reduce alcohol intake and the alcohol preference without interfering with total fluid intake and without creating an alcohol aversion. -5- 26 0 89 gxaropls 2 Rats drinking 0.1 mg/ml cocaine for a week, followed by a week of cocaine withdrawal, reveal a preference for cocaine when given the choice between 0.1 mg/ml cocaine and water in the third week. Ritanserin, given once daily during both the period 5 of cocaine withdrawal and choice between cocaine and water, reduces the preference for cocaine as well as the total amount of cocaine consumed. At 10 mg/kg ritanserin, cocaine intake was reduced by about 30%. Reduction in cocaine intake was accompanied by an increased water consumption keeping total fluid intake constant Reduction in preference for cocaine remained present at doses down to 2.5 mg/kg ritanserin. However, at the 10 tested doses a complete cocaine aversion was not obseryed, because the test animals continued to consume some quantity of cocaine. Ritanserin's activity was present from the first day of choice and the drug remained active during the entire period of choice.
Example 3 Rats given the choice between fentanyl and water developed a preference for fentanyl after a first period of exposure to fentanyl alone. Ritanserin was administered subcutaneously once daily. At 2.5 mg/kg ritanserin, the highest dose tested, fentanyl intake and fentanyl preference reduced by 50 and 33%, respectively. A reduction of fentanyl preference was observed at doses down to 0.04 mg/kg and was present from 20 the first day of treatment. The reduction in fentanyl intake was compensated by an increase in water drinking. At no time there was a systematic interference of ritanserin with consumatory physiological processes nor did ritanserin create any fentanyl aversion. Furthermore, ritanserin did not affect the discriminative stimulus properties of fentanyl. * 26 0 8JL6
Claims (5)
1. Use of a compound of formula £f F 5 F or a pharmaceutically acceptable acid addition salt thereof, wherein A represents -CH=CH- or -S-, for the manufacture of a medicament for alleviating, suppressing or overcoming addiction to habit-forming drugs.
2. Use of a compound of formula (I) as defined in claim 1 for the manufacture of a medicament for treating individuals addicted to habit-forming drugs suffering from symptoms related to the withdrawal or abstention of said drugs. 15
3. Use according to claims 1 or 2 wherein A is S.
4. Use according to claim 3 wherein the habit-forming drug is alcohol, cocaine or
5. Use according to any one of claims 1 to 4, substantially as hereinbefore described 20 with reference to the Examples. 10 fentanyl. 25 END OF CLAIMS RUSSELL McVEAGH WEST WALKER per ATTORNEYS FOR THE APPLICANT
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US53717590A | 1990-06-13 | 1990-06-13 | |
| NZ23837091 | 1991-05-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NZ260896A true NZ260896A (en) | 1997-07-27 |
Family
ID=26650980
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NZ260896A NZ260896A (en) | 1990-06-13 | 1991-05-31 | Use of 2-[4-[bis(4-fluorophenyl)methylene]-1-piperidinyl]ethyl substituted thiazolopyrimidinone and -pyridopyrimidinone derivatives for preparing medicaments for treating addiction |
Country Status (1)
| Country | Link |
|---|---|
| NZ (1) | NZ260896A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11977085B1 (en) | 2023-09-05 | 2024-05-07 | Elan Ehrlich | Date rape drug detection device and method of using same |
-
1991
- 1991-05-31 NZ NZ260896A patent/NZ260896A/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11977085B1 (en) | 2023-09-05 | 2024-05-07 | Elan Ehrlich | Date rape drug detection device and method of using same |
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