UA57859C2 - СКЛАДНІ ЕФІРИ (+)-АЛЬФА-(2,3-ДИМЕТОКСИФЕНІЛ)-1-[2-(4-ФТОРФЕНІЛ)ЕТИЛ]-4-ПІПЕРИДИНМЕТАНОЛУ, СПОСІБ ЇХ ОТРИМАННЯ, ФАРМАЦЕВТИЧНА КОМПОЗИЦІЯ, СПОСІБ ІНГІБУВАННЯ ДІЇ СЕРОТОНІНУ НА 5HT2A РЕЦЕПТОР, СПОСІБ ЛІКУВАННЯ - Google Patents

СКЛАДНІ ЕФІРИ (+)-АЛЬФА-(2,3-ДИМЕТОКСИФЕНІЛ)-1-[2-(4-ФТОРФЕНІЛ)ЕТИЛ]-4-ПІПЕРИДИНМЕТАНОЛУ, СПОСІБ ЇХ ОТРИМАННЯ, ФАРМАЦЕВТИЧНА КОМПОЗИЦІЯ, СПОСІБ ІНГІБУВАННЯ ДІЇ СЕРОТОНІНУ НА 5HT2A РЕЦЕПТОР, СПОСІБ ЛІКУВАННЯ Download PDF

Info

Publication number: UA57859C2
Authority: UA; Ukraine
Prior art keywords: compound; ethyl; fluorophenyl; dimethoxyphenyl; alkyl
Prior art date: 1998-10-14

Application number

UA2001042522A

Other languages

English (en)

Russian (ru)

Ukrainian (uk)

Inventor

Альберт А. Карр

Хейфте Люк Е. Ван

мол. КОСЛІ Реймонд В.

Original Assignee

Авентіс Фармасьютікалз Інк.

Авентис Фармасьютикалз Инк.

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

1998-10-14

Filing date

1998-10-14

Publication date

2003-07-15

1998-10-14 Application filed by Авентіс Фармасьютікалз Інк., Авентис Фармасьютикалз Инк. filed Critical Авентіс Фармасьютікалз Інк.

2003-07-15 Publication of UA57859C2 publication Critical patent/UA57859C2/uk

Links

238000000034 method Methods 0.000 title claims description 32
238000011282 treatment Methods 0.000 title claims description 27
QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 title claims description 16
229940076279 serotonin Drugs 0.000 title claims description 8
239000008194 pharmaceutical composition Substances 0.000 title claims description 7
230000005764 inhibitory process Effects 0.000 title claims description 6
230000000694 effects Effects 0.000 title description 15
238000002360 preparation method Methods 0.000 title description 10
150000002148 esters Chemical class 0.000 title description 4
150000001875 compounds Chemical class 0.000 claims description 72
239000003921 oil Substances 0.000 claims description 33
235000019198 oils Nutrition 0.000 claims description 33
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 21
150000003839 salts Chemical class 0.000 claims description 18
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 16
208000020016 psychiatric disease Diseases 0.000 claims description 14
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 13
201000000980 schizophrenia Diseases 0.000 claims description 13
208000019901 Anxiety disease Diseases 0.000 claims description 11
201000010099 disease Diseases 0.000 claims description 11
208000020925 Bipolar disease Diseases 0.000 claims description 10
239000002253 acid Substances 0.000 claims description 10
150000008065 acid anhydrides Chemical class 0.000 claims description 9
208000011117 substance-related disease Diseases 0.000 claims description 9
230000009471 action Effects 0.000 claims description 8
125000000217 alkyl group Chemical group 0.000 claims description 8
230000036506 anxiety Effects 0.000 claims description 8
206010013663 drug dependence Diseases 0.000 claims description 8
208000021384 Obsessive-Compulsive disease Diseases 0.000 claims description 7
239000000460 chlorine Substances 0.000 claims description 7
239000003937 drug carrier Substances 0.000 claims description 7
239000008159 sesame oil Substances 0.000 claims description 7
235000011803 sesame oil Nutrition 0.000 claims description 7
208000007536 Thrombosis Diseases 0.000 claims description 6
206010003225 Arteriospasm coronary Diseases 0.000 claims description 5
208000003890 Coronary Vasospasm Diseases 0.000 claims description 5
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 5
229910052801 chlorine Inorganic materials 0.000 claims description 5
201000011634 coronary artery vasospasm Diseases 0.000 claims description 5
230000015572 biosynthetic process Effects 0.000 claims description 4
208000028683 bipolar I disease Diseases 0.000 claims description 4
208000025307 bipolar depression Diseases 0.000 claims description 4
125000001309 chloro group Chemical group Cl* 0.000 claims description 4
150000004820 halides Chemical class 0.000 claims description 4
230000002401 inhibitory effect Effects 0.000 claims description 4
244000144725 Amygdalus communis Species 0.000 claims description 2
235000011437 Amygdalus communis Nutrition 0.000 claims description 2
206010002383 Angina Pectoris Diseases 0.000 claims description 2
235000017060 Arachis glabrata Nutrition 0.000 claims description 2
244000105624 Arachis hypogaea Species 0.000 claims description 2
235000010777 Arachis hypogaea Nutrition 0.000 claims description 2
235000018262 Arachis monticola Nutrition 0.000 claims description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
240000007817 Olea europaea Species 0.000 claims description 2
235000003434 Sesamum indicum Nutrition 0.000 claims description 2
240000008042 Zea mays Species 0.000 claims description 2
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 claims description 2
235000002017 Zea mays subsp mays Nutrition 0.000 claims description 2
235000020224 almond Nutrition 0.000 claims description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
229910052794 bromium Chemical group 0.000 claims description 2
239000004359 castor oil Substances 0.000 claims description 2
235000019438 castor oil Nutrition 0.000 claims description 2
235000005822 corn Nutrition 0.000 claims description 2
235000012343 cottonseed oil Nutrition 0.000 claims description 2
239000002385 cottonseed oil Substances 0.000 claims description 2
ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 claims description 2
235000020232 peanut Nutrition 0.000 claims description 2
244000000231 Sesamum indicum Species 0.000 claims 1
239000013543 active substance Substances 0.000 claims 1
235000021400 peanut butter Nutrition 0.000 claims 1
238000012876 topography Methods 0.000 claims 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 63
239000000243 solution Substances 0.000 description 63
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 39
241001465754 Metazoa Species 0.000 description 38
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 35
239000000203 mixture Substances 0.000 description 31
229930006000 Sucrose Natural products 0.000 description 29
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 29
239000005720 sucrose Substances 0.000 description 29
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 25
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
239000000126 substance Substances 0.000 description 19
238000003756 stirring Methods 0.000 description 17
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 16
208000013738 Sleep Initiation and Maintenance disease Diseases 0.000 description 16
206010022437 insomnia Diseases 0.000 description 16
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 14
208000020401 Depressive disease Diseases 0.000 description 14
239000010410 layer Substances 0.000 description 14
239000002904 solvent Substances 0.000 description 14
239000004480 active ingredient Substances 0.000 description 13
229940079593 drug Drugs 0.000 description 13
239000003814 drug Substances 0.000 description 13
239000007787 solid Substances 0.000 description 13
241000700159 Rattus Species 0.000 description 12
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
238000000921 elemental analysis Methods 0.000 description 12
229920006395 saturated elastomer Polymers 0.000 description 12
239000000741 silica gel Substances 0.000 description 12
229910002027 silica gel Inorganic materials 0.000 description 12
206010026749 Mania Diseases 0.000 description 11
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 11
238000006243 chemical reaction Methods 0.000 description 11
239000011541 reaction mixture Substances 0.000 description 11
238000012360 testing method Methods 0.000 description 11
239000002585 base Substances 0.000 description 10
230000006399 behavior Effects 0.000 description 9
235000019439 ethyl acetate Nutrition 0.000 description 9
239000012044 organic layer Substances 0.000 description 9
239000012266 salt solution Substances 0.000 description 9
-1 2-(4-fluorophenyl)ethyl Chemical group 0.000 description 8
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 8
238000004587 chromatography analysis Methods 0.000 description 8
230000007958 sleep Effects 0.000 description 8
208000024891 symptom Diseases 0.000 description 8
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 7
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
235000013305 food Nutrition 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
208000012322 Raynaud phenomenon Diseases 0.000 description 6
150000008064 anhydrides Chemical class 0.000 description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
208000001640 Fibromyalgia Diseases 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
208000003782 Raynaud disease Diseases 0.000 description 5
239000007864 aqueous solution Substances 0.000 description 5
230000037396 body weight Effects 0.000 description 5
208000035475 disorder Diseases 0.000 description 5
239000000706 filtrate Substances 0.000 description 5
BCGWQEUPMDMJNV-UHFFFAOYSA-N imipramine Chemical compound C1CC2=CC=CC=C2N(CCCN(C)C)C2=CC=CC=C21 BCGWQEUPMDMJNV-UHFFFAOYSA-N 0.000 description 5
229960004801 imipramine Drugs 0.000 description 5
208000024714 major depressive disease Diseases 0.000 description 5
238000013268 sustained release Methods 0.000 description 5
239000012730 sustained-release form Substances 0.000 description 5
PMEJZQCLNZXYDL-UHFFFAOYSA-N 2,2-dimethyloct-3-enoic acid Chemical compound CCCCC=CC(C)(C)C(O)=O PMEJZQCLNZXYDL-UHFFFAOYSA-N 0.000 description 4
208000000103 Anorexia Nervosa Diseases 0.000 description 4
206010012374 Depressed mood Diseases 0.000 description 4
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
239000012300 argon atmosphere Substances 0.000 description 4
206010003119 arrhythmia Diseases 0.000 description 4
230000006793 arrhythmia Effects 0.000 description 4
230000001684 chronic effect Effects 0.000 description 4
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 description 4
239000012230 colorless oil Substances 0.000 description 4
208000024732 dysthymic disease Diseases 0.000 description 4
238000005886 esterification reaction Methods 0.000 description 4
238000002474 experimental method Methods 0.000 description 4
239000000284 extract Substances 0.000 description 4
238000001914 filtration Methods 0.000 description 4
229910052736 halogen Inorganic materials 0.000 description 4
238000006460 hydrolysis reaction Methods 0.000 description 4
238000002347 injection Methods 0.000 description 4
239000007924 injection Substances 0.000 description 4
238000004949 mass spectrometry Methods 0.000 description 4
239000000047 product Substances 0.000 description 4
230000002035 prolonged effect Effects 0.000 description 4
102000005962 receptors Human genes 0.000 description 4
108020003175 receptors Proteins 0.000 description 4
FLRUNCJXOVYWDH-UHFFFAOYSA-N 1-(2-bromoethyl)-4-fluorobenzene Chemical compound FC1=CC=C(CCBr)C=C1 FLRUNCJXOVYWDH-UHFFFAOYSA-N 0.000 description 3
125000001617 2,3-dimethoxy phenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C(OC([H])([H])[H])=C1[H] 0.000 description 3
LEDHSIIGSCUMAW-UHFFFAOYSA-N 4-(2,3-dimethoxyphenyl)piperidine-4-carbaldehyde Chemical compound COC1=CC=CC(C2(CCNCC2)C=O)=C1OC LEDHSIIGSCUMAW-UHFFFAOYSA-N 0.000 description 3
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 3
DIWVBIXQCNRCFE-UHFFFAOYSA-N DL-alpha-Methoxyphenylacetic acid Chemical compound COC(C(O)=O)C1=CC=CC=C1 DIWVBIXQCNRCFE-UHFFFAOYSA-N 0.000 description 3
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
239000005557 antagonist Substances 0.000 description 3
230000003542 behavioural effect Effects 0.000 description 3
IPIVAXLHTVNRBS-UHFFFAOYSA-N decanoyl chloride Chemical compound CCCCCCCCCC(Cl)=O IPIVAXLHTVNRBS-UHFFFAOYSA-N 0.000 description 3
238000005516 engineering process Methods 0.000 description 3
230000032050 esterification Effects 0.000 description 3
IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 3
230000007062 hydrolysis Effects 0.000 description 3
230000003340 mental effect Effects 0.000 description 3
150000002825 nitriles Chemical class 0.000 description 3
239000012299 nitrogen atmosphere Substances 0.000 description 3
231100000252 nontoxic Toxicity 0.000 description 3
230000003000 nontoxic effect Effects 0.000 description 3
230000001575 pathological effect Effects 0.000 description 3
210000002381 plasma Anatomy 0.000 description 3
229910000027 potassium carbonate Inorganic materials 0.000 description 3
230000002829 reductive effect Effects 0.000 description 3
239000012047 saturated solution Substances 0.000 description 3
201000002859 sleep apnea Diseases 0.000 description 3
208000011580 syndromic disease Diseases 0.000 description 3
ZCHHRLHTBGRGOT-SNAWJCMRSA-N (E)-hex-2-en-1-ol Chemical compound CCC\C=C\CO ZCHHRLHTBGRGOT-SNAWJCMRSA-N 0.000 description 2
IKNDGHRNXGEHTO-UHFFFAOYSA-N 2,2-dimethyloctanoic acid Chemical compound CCCCCCC(C)(C)C(O)=O IKNDGHRNXGEHTO-UHFFFAOYSA-N 0.000 description 2
JIVGSHFYXPRRSZ-UHFFFAOYSA-N 2,3-dimethoxybenzaldehyde Chemical compound COC1=CC=CC(C=O)=C1OC JIVGSHFYXPRRSZ-UHFFFAOYSA-N 0.000 description 2
OXQGTIUCKGYOAA-UHFFFAOYSA-N 2-Ethylbutanoic acid Chemical compound CCC(CC)C(O)=O OXQGTIUCKGYOAA-UHFFFAOYSA-N 0.000 description 2
IGIDLTISMCAULB-UHFFFAOYSA-N 3-methylvaleric acid Chemical compound CCC(C)CC(O)=O IGIDLTISMCAULB-UHFFFAOYSA-N 0.000 description 2
QCMFUJYCRNASBU-UHFFFAOYSA-N 4-(2,3-dimethoxybenzoyl)piperidine-1-carboxylic acid Chemical compound COC1=CC=CC(C(=O)C2CCN(CC2)C(O)=O)=C1OC QCMFUJYCRNASBU-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
208000007415 Anhedonia Diseases 0.000 description 2
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
206010010144 Completed suicide Diseases 0.000 description 2
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
208000027776 Extrapyramidal disease Diseases 0.000 description 2
208000004547 Hallucinations Diseases 0.000 description 2
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
206010022562 Intermittent claudication Diseases 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
206010028347 Muscle twitching Diseases 0.000 description 2
206010052904 Musculoskeletal stiffness Diseases 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
201000001068 Prinzmetal angina Diseases 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
241000700157 Rattus norvegicus Species 0.000 description 2
241000283984 Rodentia Species 0.000 description 2
206010041349 Somnolence Diseases 0.000 description 2
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
230000001154 acute effect Effects 0.000 description 2
239000000654 additive Substances 0.000 description 2
229910052784 alkaline earth metal Inorganic materials 0.000 description 2
238000000540 analysis of variance Methods 0.000 description 2
208000022531 anorexia Diseases 0.000 description 2
230000003042 antagnostic effect Effects 0.000 description 2
230000008485 antagonism Effects 0.000 description 2
230000008901 benefit Effects 0.000 description 2
210000004369 blood Anatomy 0.000 description 2
239000008280 blood Substances 0.000 description 2
RYYVLZVUVIJVGH-UHFFFAOYSA-N caffeine Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2C RYYVLZVUVIJVGH-UHFFFAOYSA-N 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
230000015556 catabolic process Effects 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
230000008859 change Effects 0.000 description 2
229960003920 cocaine Drugs 0.000 description 2
230000002920 convulsive effect Effects 0.000 description 2
238000001816 cooling Methods 0.000 description 2
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
230000007423 decrease Effects 0.000 description 2
206010061428 decreased appetite Diseases 0.000 description 2
POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 2
238000010828 elution Methods 0.000 description 2
238000013504 emergency use authorization Methods 0.000 description 2
125000001207 fluorophenyl group Chemical group 0.000 description 2
LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 2
KEMQGTRYUADPNZ-UHFFFAOYSA-N heptadecanoic acid Chemical compound CCCCCCCCCCCCCCCCC(O)=O KEMQGTRYUADPNZ-UHFFFAOYSA-N 0.000 description 2
YWGHUJQYGPDNKT-UHFFFAOYSA-N hexanoyl chloride Chemical compound CCCCCC(Cl)=O YWGHUJQYGPDNKT-UHFFFAOYSA-N 0.000 description 2
238000004128 high performance liquid chromatography Methods 0.000 description 2
150000004679 hydroxides Chemical class 0.000 description 2
VKOBVWXKNCXXDE-UHFFFAOYSA-N icosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCC(O)=O VKOBVWXKNCXXDE-UHFFFAOYSA-N 0.000 description 2
230000003993 interaction Effects 0.000 description 2
208000021156 intermittent vascular claudication Diseases 0.000 description 2
238000007918 intramuscular administration Methods 0.000 description 2
SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 2
FGKJLKRYENPLQH-UHFFFAOYSA-N isocaproic acid Chemical compound CC(C)CCC(O)=O FGKJLKRYENPLQH-UHFFFAOYSA-N 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
WSFSSNUMVMOOMR-BJUDXGSMSA-N methanone Chemical compound O=[11CH2] WSFSSNUMVMOOMR-BJUDXGSMSA-N 0.000 description 2
150000007522 mineralic acids Chemical class 0.000 description 2
230000036651 mood Effects 0.000 description 2
230000002107 myocardial effect Effects 0.000 description 2
WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 2
FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 description 2
150000007524 organic acids Chemical class 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
238000007911 parenteral administration Methods 0.000 description 2
230000001766 physiological effect Effects 0.000 description 2
XBXHCBLBYQEYTI-UHFFFAOYSA-N piperidin-4-ylmethanol Chemical compound OCC1CCNCC1 XBXHCBLBYQEYTI-UHFFFAOYSA-N 0.000 description 2
239000011591 potassium Substances 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
235000011181 potassium carbonates Nutrition 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
238000010992 reflux Methods 0.000 description 2
238000010079 rubber tapping Methods 0.000 description 2
208000019116 sleep disease Diseases 0.000 description 2
239000011734 sodium Substances 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000007858 starting material Substances 0.000 description 2
DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 2
230000001225 therapeutic effect Effects 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
210000001519 tissue Anatomy 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
SZHOJFHSIKHZHA-UHFFFAOYSA-N tridecanoic acid Chemical compound CCCCCCCCCCCCC(O)=O SZHOJFHSIKHZHA-UHFFFAOYSA-N 0.000 description 2
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical compound CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 description 2
NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 2
ABDKAPXRBAPSQN-UHFFFAOYSA-N veratrole Chemical compound COC1=CC=CC=C1OC ABDKAPXRBAPSQN-UHFFFAOYSA-N 0.000 description 2
HXTGXYRHXAGCFP-UHFFFAOYSA-N volinanserin Chemical compound COC1=CC=CC(C(O)C2CCN(CCC=3C=CC(F)=CC=3)CC2)=C1OC HXTGXYRHXAGCFP-UHFFFAOYSA-N 0.000 description 2
238000005303 weighing Methods 0.000 description 2
SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 description 1
XMAYWYJOQHXEEK-OZXSUGGESA-N (2R,4S)-ketoconazole Chemical compound C1CN(C(=O)C)CCN1C(C=C1)=CC=C1OC[C@@H]1O[C@@](CN2C=NC=C2)(C=2C(=CC(Cl)=CC=2)Cl)OC1 XMAYWYJOQHXEEK-OZXSUGGESA-N 0.000 description 1
KPJZHOPZRAFDTN-ZRGWGRIASA-N (6aR,9R)-N-[(2S)-1-hydroxybutan-2-yl]-4,7-dimethyl-6,6a,8,9-tetrahydroindolo[4,3-fg]quinoline-9-carboxamide Chemical compound C1=CC(C=2[C@H](N(C)C[C@@H](C=2)C(=O)N[C@H](CO)CC)C2)=C3C2=CN(C)C3=C1 KPJZHOPZRAFDTN-ZRGWGRIASA-N 0.000 description 1
ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 description 1
QVFDMWGKHUFODK-UHFFFAOYSA-N 1-(4-iodo-2,5-dimethoxyphenyl)propan-2-amine;hydrochloride Chemical compound Cl.COC1=CC(CC(C)N)=C(OC)C=C1I QVFDMWGKHUFODK-UHFFFAOYSA-N 0.000 description 1
GYSCBCSGKXNZRH-UHFFFAOYSA-N 1-benzothiophene-2-carboxamide Chemical compound C1=CC=C2SC(C(=O)N)=CC2=C1 GYSCBCSGKXNZRH-UHFFFAOYSA-N 0.000 description 1
USGHIMJARYRESV-UHFFFAOYSA-N 1-ethylpiperidine-4-carboxamide Chemical compound CCN1CCC(C(N)=O)CC1 USGHIMJARYRESV-UHFFFAOYSA-N 0.000 description 1
XYHKNCXZYYTLRG-UHFFFAOYSA-N 1h-imidazole-2-carbaldehyde Chemical compound O=CC1=NC=CN1 XYHKNCXZYYTLRG-UHFFFAOYSA-N 0.000 description 1
VUAXHMVRKOTJKP-UHFFFAOYSA-N 2,2-dimethylbutyric acid Chemical compound CCC(C)(C)C(O)=O VUAXHMVRKOTJKP-UHFFFAOYSA-N 0.000 description 1
PWMYBNYORINWQV-UHFFFAOYSA-N 2,2-dimethyloct-3-ene Chemical compound CCCCC=CC(C)(C)C PWMYBNYORINWQV-UHFFFAOYSA-N 0.000 description 1
LQIIEHBULBHJKX-UHFFFAOYSA-N 2-methylpropylalumane Chemical compound CC(C)C[AlH2] LQIIEHBULBHJKX-UHFFFAOYSA-N 0.000 description 1
BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
MLMQPDHYNJCQAO-UHFFFAOYSA-N 3,3-dimethylbutyric acid Chemical compound CC(C)(C)CC(O)=O MLMQPDHYNJCQAO-UHFFFAOYSA-N 0.000 description 1
PAVNZLVXYJDFNR-UHFFFAOYSA-N 3,3-dimethyloxane-2,6-dione Chemical compound CC1(C)CCC(=O)OC1=O PAVNZLVXYJDFNR-UHFFFAOYSA-N 0.000 description 1
GWYFCOCPABKNJV-UHFFFAOYSA-M 3-Methylbutanoic acid Natural products CC(C)CC([O-])=O GWYFCOCPABKNJV-UHFFFAOYSA-M 0.000 description 1
OQEBBZSWEGYTPG-UHFFFAOYSA-N 3-aminobutanoic acid Chemical compound CC(N)CC(O)=O OQEBBZSWEGYTPG-UHFFFAOYSA-N 0.000 description 1
ISULZYQDGYXDFW-UHFFFAOYSA-N 3-methylbutanoyl chloride Chemical compound CC(C)CC(Cl)=O ISULZYQDGYXDFW-UHFFFAOYSA-N 0.000 description 1
SFWWGMKXCYLZEG-UHFFFAOYSA-N 3-methylmorpholine Chemical class CC1COCCN1 SFWWGMKXCYLZEG-UHFFFAOYSA-N 0.000 description 1
FJBKIMJIMHITKZ-UHFFFAOYSA-N 4-(2,3-dimethoxyphenyl)piperidine-4-carbaldehyde;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.COC1=CC=CC(C2(CCNCC2)C=O)=C1OC FJBKIMJIMHITKZ-UHFFFAOYSA-N 0.000 description 1
DPBWFNDFMCCGGJ-UHFFFAOYSA-N 4-Piperidine carboxamide Chemical compound NC(=O)C1CCNCC1 DPBWFNDFMCCGGJ-UHFFFAOYSA-N 0.000 description 1
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 1
229940127239 5 Hydroxytryptamine receptor antagonist Drugs 0.000 description 1
AWQSAIIDOMEEOD-UHFFFAOYSA-N 5,5-Dimethyl-4-(3-oxobutyl)dihydro-2(3H)-furanone Chemical compound CC(=O)CCC1CC(=O)OC1(C)C AWQSAIIDOMEEOD-UHFFFAOYSA-N 0.000 description 1
102000040125 5-hydroxytryptamine receptor family Human genes 0.000 description 1
108091032151 5-hydroxytryptamine receptor family Proteins 0.000 description 1
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
206010001497 Agitation Diseases 0.000 description 1
206010001540 Akathisia Diseases 0.000 description 1
101100270230 Arabidopsis thaliana ARF7 gene Proteins 0.000 description 1
101100366098 Caenorhabditis elegans snpc-4 gene Proteins 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
208000024172 Cardiovascular disease Diseases 0.000 description 1
241000700199 Cavia porcellus Species 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
208000019888 Circadian rhythm sleep disease Diseases 0.000 description 1
GHVNFZFCNZKVNT-UHFFFAOYSA-N Decanoic acid Natural products CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 1
206010011971 Decreased interest Diseases 0.000 description 1
206010012218 Delirium Diseases 0.000 description 1
206010012239 Delusion Diseases 0.000 description 1
206010013496 Disturbance in attention Diseases 0.000 description 1
206010013654 Drug abuse Diseases 0.000 description 1
208000014094 Dystonic disease Diseases 0.000 description 1
102100029503 E3 ubiquitin-protein ligase TRIM32 Human genes 0.000 description 1
241000282326 Felis catus Species 0.000 description 1
208000010412 Glaucoma Diseases 0.000 description 1
239000007818 Grignard reagent Substances 0.000 description 1
101000634982 Homo sapiens E3 ubiquitin-protein ligase TRIM32 Proteins 0.000 description 1
206010020710 Hyperphagia Diseases 0.000 description 1
206010020772 Hypertension Diseases 0.000 description 1
206010022998 Irritability Diseases 0.000 description 1
LPHGQDQBBGAPDZ-UHFFFAOYSA-N Isocaffeine Natural products CN1C(=O)N(C)C(=O)C2=C1N(C)C=N2 LPHGQDQBBGAPDZ-UHFFFAOYSA-N 0.000 description 1
208000001456 Jet Lag Syndrome Diseases 0.000 description 1
239000005639 Lauric acid Substances 0.000 description 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
239000012359 Methanesulfonyl chloride Substances 0.000 description 1
229940123379 Methyltransferase inhibitor Drugs 0.000 description 1
UEQUQVLFIPOEMF-UHFFFAOYSA-N Mianserin Chemical compound C1C2=CC=CC=C2N2CCN(C)CC2C2=CC=CC=C21 UEQUQVLFIPOEMF-UHFFFAOYSA-N 0.000 description 1
208000019695 Migraine disease Diseases 0.000 description 1
241000699666 Mus <mouse, genus> Species 0.000 description 1
208000000112 Myalgia Diseases 0.000 description 1
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-diisopropylethylamine Substances CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 1
101150034699 Nudt3 gene Proteins 0.000 description 1
208000002193 Pain Diseases 0.000 description 1
235000021314 Palmitic acid Nutrition 0.000 description 1
206010034010 Parkinsonism Diseases 0.000 description 1
235000019483 Peanut oil Nutrition 0.000 description 1
208000018262 Peripheral vascular disease Diseases 0.000 description 1
241000009328 Perro Species 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
241000288906 Primates Species 0.000 description 1
208000001431 Psychomotor Agitation Diseases 0.000 description 1
206010037211 Psychomotor hyperactivity Diseases 0.000 description 1
208000028017 Psychotic disease Diseases 0.000 description 1
241000207961 Sesamum Species 0.000 description 1
208000010340 Sleep Deprivation Diseases 0.000 description 1
208000032140 Sleepiness Diseases 0.000 description 1
206010041235 Snoring Diseases 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
235000021355 Stearic acid Nutrition 0.000 description 1
208000032109 Transient ischaemic attack Diseases 0.000 description 1
206010044565 Tremor Diseases 0.000 description 1
229940123445 Tricyclic antidepressant Drugs 0.000 description 1
DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 1
244000126014 Valeriana officinalis Species 0.000 description 1
235000013832 Valeriana officinalis Nutrition 0.000 description 1
206010047163 Vasospasm Diseases 0.000 description 1
230000002159 abnormal effect Effects 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
230000036982 action potential Effects 0.000 description 1
230000000996 additive effect Effects 0.000 description 1
239000002671 adjuvant Substances 0.000 description 1
230000002776 aggregation Effects 0.000 description 1
238000004220 aggregation Methods 0.000 description 1
125000002723 alicyclic group Chemical group 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
239000003513 alkali Substances 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
230000003444 anaesthetic effect Effects 0.000 description 1
238000010171 animal model Methods 0.000 description 1
230000003288 anthiarrhythmic effect Effects 0.000 description 1
230000001430 anti-depressive effect Effects 0.000 description 1
230000000561 anti-psychotic effect Effects 0.000 description 1
239000000935 antidepressant agent Substances 0.000 description 1
229940005513 antidepressants Drugs 0.000 description 1
239000003420 antiserotonin agent Substances 0.000 description 1
230000036528 appetite Effects 0.000 description 1
235000019789 appetite Nutrition 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
229910052786 argon Inorganic materials 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
239000003693 atypical antipsychotic agent Substances 0.000 description 1
229940127236 atypical antipsychotics Drugs 0.000 description 1
229910052788 barium Inorganic materials 0.000 description 1
DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
238000009227 behaviour therapy Methods 0.000 description 1
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
235000019445 benzyl alcohol Nutrition 0.000 description 1
GONOPSZTUGRENK-UHFFFAOYSA-N benzyl(trichloro)silane Chemical compound Cl[Si](Cl)(Cl)CC1=CC=CC=C1 GONOPSZTUGRENK-UHFFFAOYSA-N 0.000 description 1
GWYFCOCPABKNJV-UHFFFAOYSA-N beta-methyl-butyric acid Natural products CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
230000000903 blocking effect Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
210000004556 brain Anatomy 0.000 description 1
239000012267 brine Substances 0.000 description 1
YHASWHZGWUONAO-UHFFFAOYSA-N butanoyl butanoate Chemical compound CCCC(=O)OC(=O)CCC YHASWHZGWUONAO-UHFFFAOYSA-N 0.000 description 1
JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
229960001948 caffeine Drugs 0.000 description 1
VJEONQKOZGKCAK-UHFFFAOYSA-N caffeine Natural products CN1C(=O)N(C)C(=O)C2=C1C=CN2C VJEONQKOZGKCAK-UHFFFAOYSA-N 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
239000011575 calcium Substances 0.000 description 1
FFGPTBGBLSHEPO-UHFFFAOYSA-N carbamazepine Chemical compound C1=CC2=CC=CC=C2N(C(=O)N)C2=CC=CC=C21 FFGPTBGBLSHEPO-UHFFFAOYSA-N 0.000 description 1
229960000623 carbamazepine Drugs 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
235000011089 carbon dioxide Nutrition 0.000 description 1
PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
230000002612 cardiopulmonary effect Effects 0.000 description 1
239000000969 carrier Substances 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
210000004027 cell Anatomy 0.000 description 1
210000003169 central nervous system Anatomy 0.000 description 1
210000003710 cerebral cortex Anatomy 0.000 description 1
ZPEIMTDSQAKGNT-UHFFFAOYSA-N chlorpromazine Chemical compound C1=C(Cl)C=C2N(CCCN(C)C)C3=CC=CC=C3SC2=C1 ZPEIMTDSQAKGNT-UHFFFAOYSA-N 0.000 description 1
229960001076 chlorpromazine Drugs 0.000 description 1
238000013375 chromatographic separation Methods 0.000 description 1
230000027288 circadian rhythm Effects 0.000 description 1
238000004140 cleaning Methods 0.000 description 1
230000001149 cognitive effect Effects 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
230000008602 contraction Effects 0.000 description 1
210000004351 coronary vessel Anatomy 0.000 description 1
208000026725 cyclothymic disease Diseases 0.000 description 1
238000007405 data analysis Methods 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
230000006735 deficit Effects 0.000 description 1
238000006731 degradation reaction Methods 0.000 description 1
231100000868 delusion Toxicity 0.000 description 1
230000000994 depressogenic effect Effects 0.000 description 1
238000011161 development Methods 0.000 description 1
AQEFLFZSWDEAIP-UHFFFAOYSA-N di-tert-butyl ether Chemical compound CC(C)(C)OC(C)(C)C AQEFLFZSWDEAIP-UHFFFAOYSA-N 0.000 description 1
235000001916 dieting Nutrition 0.000 description 1
230000037228 dieting effect Effects 0.000 description 1
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical class CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
238000004821 distillation Methods 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
NQGIJDNPUZEBRU-UHFFFAOYSA-N dodecanoyl chloride Chemical compound CCCCCCCCCCCC(Cl)=O NQGIJDNPUZEBRU-UHFFFAOYSA-N 0.000 description 1
229960003638 dopamine Drugs 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
231100000673 dose–response relationship Toxicity 0.000 description 1
238000001647 drug administration Methods 0.000 description 1
239000003480 eluent Substances 0.000 description 1
230000002996 emotional effect Effects 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
230000003511 endothelial effect Effects 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000005713 exacerbation Effects 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000000945 filler Substances 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
210000004744 fore-foot Anatomy 0.000 description 1
238000009472 formulation Methods 0.000 description 1
239000012458 free base Substances 0.000 description 1
150000004795 grignard reagents Chemical class 0.000 description 1
229960003878 haloperidol Drugs 0.000 description 1
230000036541 health Effects 0.000 description 1
ICDQUAGMQCUEMY-UHFFFAOYSA-N heptadecanoyl chloride Chemical compound CCCCCCCCCCCCCCCCC(Cl)=O ICDQUAGMQCUEMY-UHFFFAOYSA-N 0.000 description 1
UCVODTZQZHMTPN-UHFFFAOYSA-N heptanoyl chloride Chemical compound CCCCCCC(Cl)=O UCVODTZQZHMTPN-UHFFFAOYSA-N 0.000 description 1
ARBOVOVUTSQWSS-UHFFFAOYSA-N hexadecanoyl chloride Chemical compound CCCCCCCCCCCCCCCC(Cl)=O ARBOVOVUTSQWSS-UHFFFAOYSA-N 0.000 description 1
QWZBEFCPZJWDKC-UHFFFAOYSA-N hexadecanoyl hexadecanoate Chemical compound CCCCCCCCCCCCCCCC(=O)OC(=O)CCCCCCCCCCCCCCC QWZBEFCPZJWDKC-UHFFFAOYSA-N 0.000 description 1
PKHMTIRCAFTBDS-UHFFFAOYSA-N hexanoyl hexanoate Chemical compound CCCCCC(=O)OC(=O)CCCCC PKHMTIRCAFTBDS-UHFFFAOYSA-N 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
UWYVPFMHMJIBHE-OWOJBTEDSA-N hydroxymaleic acid group Chemical group O/C(/C(=O)O)=C/C(=O)O UWYVPFMHMJIBHE-OWOJBTEDSA-N 0.000 description 1
239000003326 hypnotic agent Substances 0.000 description 1
230000000147 hypnotic effect Effects 0.000 description 1
230000001771 impaired effect Effects 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
238000010255 intramuscular injection Methods 0.000 description 1
239000007927 intramuscular injection Substances 0.000 description 1
YAQXGBBDJYBXKL-UHFFFAOYSA-N iron(2+);1,10-phenanthroline;dicyanide Chemical compound [Fe+2].N#[C-].N#[C-].C1=CN=C2C3=NC=CC=C3C=CC2=C1.C1=CN=C2C3=NC=CC=C3C=CC2=C1 YAQXGBBDJYBXKL-UHFFFAOYSA-N 0.000 description 1
LSACYLWPPQLVSM-UHFFFAOYSA-N isobutyric acid anhydride Chemical compound CC(C)C(=O)OC(=O)C(C)C LSACYLWPPQLVSM-UHFFFAOYSA-N 0.000 description 1
LRDFRRGEGBBSRN-UHFFFAOYSA-N isobutyronitrile Chemical compound CC(C)C#N LRDFRRGEGBBSRN-UHFFFAOYSA-N 0.000 description 1
208000033915 jet lag type circadian rhythm sleep disease Diseases 0.000 description 1
229960004125 ketoconazole Drugs 0.000 description 1
231100000636 lethal dose Toxicity 0.000 description 1
230000000670 limiting effect Effects 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
229960001078 lithium Drugs 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
239000000463 material Substances 0.000 description 1
230000013011 mating Effects 0.000 description 1
201000003995 melancholia Diseases 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
230000002503 metabolic effect Effects 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
239000003697 methyltransferase inhibitor Substances 0.000 description 1
229960001186 methysergide Drugs 0.000 description 1
229960003955 mianserin Drugs 0.000 description 1
206010027599 migraine Diseases 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
235000010446 mineral oil Nutrition 0.000 description 1
210000003205 muscle Anatomy 0.000 description 1
208000013465 muscle pain Diseases 0.000 description 1
125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
FUZZWVXGSFPDMH-UHFFFAOYSA-N n-hexanoic acid Natural products CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
229940105631 nembutal Drugs 0.000 description 1
239000003176 neuroleptic agent Substances 0.000 description 1
229960002715 nicotine Drugs 0.000 description 1
SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
NTQYXUJLILNTFH-UHFFFAOYSA-N nonanoyl chloride Chemical compound CCCCCCCCC(Cl)=O NTQYXUJLILNTFH-UHFFFAOYSA-N 0.000 description 1
230000000414 obstructive effect Effects 0.000 description 1
208000001797 obstructive sleep apnea Diseases 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
WTBAHSZERDXKKZ-UHFFFAOYSA-N octadecanoyl chloride Chemical compound CCCCCCCCCCCCCCCCCC(Cl)=O WTBAHSZERDXKKZ-UHFFFAOYSA-N 0.000 description 1
RAFYDKXYXRZODZ-UHFFFAOYSA-N octanoyl octanoate Chemical compound CCCCCCCC(=O)OC(=O)CCCCCCC RAFYDKXYXRZODZ-UHFFFAOYSA-N 0.000 description 1
239000012053 oil suspension Substances 0.000 description 1
229940005483 opioid analgesics Drugs 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
235000020830 overeating Nutrition 0.000 description 1
230000036407 pain Effects 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
239000000312 peanut oil Substances 0.000 description 1
XGISHOFUAFNYQF-UHFFFAOYSA-N pentanoyl chloride Chemical compound CCCCC(Cl)=O XGISHOFUAFNYQF-UHFFFAOYSA-N 0.000 description 1
WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 1
230000000737 periodic effect Effects 0.000 description 1
230000002093 peripheral effect Effects 0.000 description 1
WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
235000011007 phosphoric acid Nutrition 0.000 description 1
150000003016 phosphoric acids Chemical class 0.000 description 1
230000035790 physiological processes and functions Effects 0.000 description 1
HDOWRFHMPULYOA-UHFFFAOYSA-N piperidin-4-ol Chemical compound OC1CCNCC1 HDOWRFHMPULYOA-UHFFFAOYSA-N 0.000 description 1
229920003023 plastic Polymers 0.000 description 1
235000015320 potassium carbonate Nutrition 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
239000000843 powder Substances 0.000 description 1
230000002360 prefrontal effect Effects 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
230000002335 preservative effect Effects 0.000 description 1
238000011321 prophylaxis Methods 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
238000010926 purge Methods 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
230000000306 recurrent effect Effects 0.000 description 1
238000011160 research Methods 0.000 description 1
230000029058 respiratory gaseous exchange Effects 0.000 description 1
210000002345 respiratory system Anatomy 0.000 description 1
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 1
229950009626 ritanserin Drugs 0.000 description 1
230000000698 schizophrenic effect Effects 0.000 description 1
230000001932 seasonal effect Effects 0.000 description 1
239000000932 sedative agent Substances 0.000 description 1
229940125723 sedative agent Drugs 0.000 description 1
239000013049 sediment Substances 0.000 description 1
230000035945 sensitivity Effects 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000003215 serotonin 5-HT2 receptor antagonist Substances 0.000 description 1
208000022925 sleep disturbance Diseases 0.000 description 1
208000020685 sleep-wake disease Diseases 0.000 description 1
230000037321 sleepiness Effects 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
239000000725 suspension Substances 0.000 description 1
230000001732 thrombotic effect Effects 0.000 description 1
230000001256 tonic effect Effects 0.000 description 1
238000012549 training Methods 0.000 description 1
239000003204 tranquilizing agent Substances 0.000 description 1
230000002936 tranquilizing effect Effects 0.000 description 1
201000010875 transient cerebral ischemia Diseases 0.000 description 1
125000005270 trialkylamine group Chemical group 0.000 description 1
150000003628 tricarboxylic acids Chemical class 0.000 description 1
239000003029 tricyclic antidepressant agent Substances 0.000 description 1
JUKPJGZUFHCZQI-UHFFFAOYSA-N undecanoyl chloride Chemical compound CCCCCCCCCCC(Cl)=O JUKPJGZUFHCZQI-UHFFFAOYSA-N 0.000 description 1
235000016788 valerian Nutrition 0.000 description 1
229940005605 valeric acid Drugs 0.000 description 1
230000002792 vascular Effects 0.000 description 1
230000002618 waking effect Effects 0.000 description 1
230000003442 weekly effect Effects 0.000 description 1
230000004584 weight gain Effects 0.000 description 1
235000019786 weight gain Nutrition 0.000 description 1
230000004580 weight loss Effects 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/20—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms
- C07D211/22—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms by oxygen atoms
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/22—Anxiolytics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/06—Antiarrhythmics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Life Sciences & Earth Sciences (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Animal Behavior & Ethology (AREA)
Pharmacology & Pharmacy (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Biomedical Technology (AREA)
Neurosurgery (AREA)
Neurology (AREA)
Psychiatry (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Diabetes (AREA)
Hematology (AREA)
Vascular Medicine (AREA)
Urology & Nephrology (AREA)
Pain & Pain Management (AREA)
Addiction (AREA)
Epidemiology (AREA)
Hydrogenated Pyridines (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

UA2001042522A 1998-10-14 1998-10-14 СКЛАДНІ ЕФІРИ (+)-АЛЬФА-(2,3-ДИМЕТОКСИФЕНІЛ)-1-[2-(4-ФТОРФЕНІЛ)ЕТИЛ]-4-ПІПЕРИДИНМЕТАНОЛУ, СПОСІБ ЇХ ОТРИМАННЯ, ФАРМАЦЕВТИЧНА КОМПОЗИЦІЯ, СПОСІБ ІНГІБУВАННЯ ДІЇ СЕРОТОНІНУ НА 5HT2A РЕЦЕПТОР, СПОСІБ ЛІКУВАННЯ UA57859C2 (uk)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
PCT/US1998/021608 WO2000021930A1 (en)	1998-10-14	1998-10-14	Esters of (+)-alpha-( 2,3- dimethoxyphenyl) -1-[2-(4- fluorophenyl) ethyl]-4- piperidinemethanol and their use as prodrugs of the 5ht2a receptor antagonist mdl 110,907

Publications (1)

Publication Number	Publication Date
UA57859C2 true UA57859C2 (uk)	2003-07-15

Family

ID=22268079

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
UA2001042522A UA57859C2 (uk)	1998-10-14	1998-10-14	СКЛАДНІ ЕФІРИ (+)-АЛЬФА-(2,3-ДИМЕТОКСИФЕНІЛ)-1-[2-(4-ФТОРФЕНІЛ)ЕТИЛ]-4-ПІПЕРИДИНМЕТАНОЛУ, СПОСІБ ЇХ ОТРИМАННЯ, ФАРМАЦЕВТИЧНА КОМПОЗИЦІЯ, СПОСІБ ІНГІБУВАННЯ ДІЇ СЕРОТОНІНУ НА 5HT<sub>2A</sub> РЕЦЕПТОР, СПОСІБ ЛІКУВАННЯ

Country Status (20)

Country	Link
EP (1)	EP1121345A1 (cs)
JP (1)	JP2002527422A (cs)
KR (1)	KR100515429B1 (cs)
CN (1)	CN1160333C (cs)
AU (1)	AU1083099A (cs)
BR (1)	BR9816049A (cs)
CA (1)	CA2347469C (cs)
CZ (1)	CZ20011331A3 (cs)
EA (1)	EA003667B1 (cs)
EE (1)	EE200100219A (cs)
HR (1)	HRP20010278A2 (cs)
HU (1)	HUP0200517A3 (cs)
IL (2)	IL142479A0 (cs)
NO (1)	NO320417B1 (cs)
NZ (1)	NZ510631A (cs)
PL (1)	PL193306B1 (cs)
SK (1)	SK5082001A3 (cs)
TR (1)	TR200101047T2 (cs)
UA (1)	UA57859C2 (cs)
WO (1)	WO2000021930A1 (cs)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US20020099076A1 (en) *	2000-05-25	2002-07-25	Richard Scheyer D.	Use of (+)-a-(2,3-dimethoxyphenyl)-1-[2-(4-fluorophenyl) ethyl]-4-piperidinemethanol or its prodrug in the treatment of symptoms of dementia and dopamine induced psychosis
CN102241667B (zh) *	2010-05-14	2013-10-23	中国人民解放军军事医学科学院毒物药物研究所	1-[(4-羟基哌啶-4基)甲基]吡啶-2(1h)-酮衍生物及其制备方法和用途
CN106892897A (zh) *	2015-12-21	2017-06-27	上海科胜药物研发有限公司	一种羟哌吡酮游离碱新晶型及其制备方法
CN106928187A (zh) *	2015-12-31	2017-07-07	上海奥博生物医药技术有限公司	一种盐酸羟哌吡酮新晶型及其制备方法
US20220273628A1 (en) *	2021-02-19	2022-09-01	Universitätsspital Basel	Effects of lysergic acid diethylamide (lsd) and of lsd analogs to assist psychotherapy for generalized anxiety disorder or other anxiety not related to life-threatening illness
EP4329759A4 (en)	2021-04-30	2025-07-16	Mind Medicine Inc	CRYSTALLINE FORMS OF LSD SALTS
JP7846211B2 (ja)	2021-08-19	2026-04-14	デフィニウムセラピューティクスユーエス，インコーポレイテッド	治療適用のためのｄ－リゼルグ酸ジエチルアミドの即時放出製剤

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CA2083698C (en) *	1990-06-01	1997-11-04	Albert A. Carr	(+)-alpha-(2,3-dimethoxyphenyl)-1- [2-(4-fluorophenyl) ethyl]-4-piperidinemethanol

1998
- 1998-10-14 CA CA002347469A patent/CA2347469C/en not_active Expired - Fee Related
- 1998-10-14 IL IL14247998A patent/IL142479A0/xx active IP Right Grant
- 1998-10-14 EA EA200100361A patent/EA003667B1/ru not_active IP Right Cessation
- 1998-10-14 BR BR9816049-4A patent/BR9816049A/pt not_active Application Discontinuation
- 1998-10-14 CZ CZ20011331A patent/CZ20011331A3/cs unknown
- 1998-10-14 JP JP2000575839A patent/JP2002527422A/ja active Pending
- 1998-10-14 NZ NZ510631A patent/NZ510631A/en active IP Right Revival
- 1998-10-14 CN CNB988142740A patent/CN1160333C/zh not_active Expired - Fee Related
- 1998-10-14 HR HR20010278A patent/HRP20010278A2/hr not_active Application Discontinuation
- 1998-10-14 HU HU0200517A patent/HUP0200517A3/hu unknown
- 1998-10-14 TR TR2001/01047T patent/TR200101047T2/xx unknown
- 1998-10-14 AU AU10830/99A patent/AU1083099A/en not_active Abandoned
- 1998-10-14 WO PCT/US1998/021608 patent/WO2000021930A1/en not_active Ceased
- 1998-10-14 KR KR10-2001-7004703A patent/KR100515429B1/ko not_active Expired - Fee Related
- 1998-10-14 EE EEP200100219A patent/EE200100219A/xx unknown
- 1998-10-14 PL PL347318A patent/PL193306B1/pl not_active IP Right Cessation
- 1998-10-14 EP EP98953458A patent/EP1121345A1/en not_active Withdrawn
- 1998-10-14 SK SK508-2001A patent/SK5082001A3/sk not_active Application Discontinuation
- 1998-10-14 UA UA2001042522A patent/UA57859C2/uk unknown
2001
- 2001-04-05 IL IL142479A patent/IL142479A/en not_active IP Right Cessation
- 2001-04-09 NO NO20011805A patent/NO320417B1/no not_active IP Right Cessation

Also Published As

Publication number	Publication date
CA2347469C (en)	2006-02-28
KR20010106517A (ko)	2001-11-29
HK1039332A1 (en)	2002-04-19
PL193306B1 (pl)	2007-01-31
CA2347469A1 (en)	2000-04-20
IL142479A0 (en)	2002-03-10
CN1160333C (zh)	2004-08-04
IL142479A (en)	2006-06-11
NO20011805L (no)	2001-06-08
NO320417B1 (no)	2005-12-05
NO20011805D0 (no)	2001-04-09
CZ20011331A3 (cs)	2001-08-15
CN1314887A (zh)	2001-09-26
TR200101047T2 (tr)	2001-08-21
EA200100361A1 (ru)	2001-10-22
PL347318A1 (en)	2002-03-25
AU1083099A (en)	2000-05-01
HRP20010278A2 (en)	2002-06-30
WO2000021930A1 (en)	2000-04-20
EP1121345A1 (en)	2001-08-08
HUP0200517A2 (en)	2002-06-29
JP2002527422A (ja)	2002-08-27
EA003667B1 (ru)	2003-08-28
NZ510631A (en)	2003-07-25
BR9816049A (pt)	2001-07-03
HUP0200517A3 (en)	2002-12-28
KR100515429B1 (ko)	2005-09-20
SK5082001A3 (en)	2001-11-06
EE200100219A (et)	2002-08-15

Publication	Publication Date	Title
US6063793A (en)	2000-05-16	Esters of (+)-α-(2,3-dimethoxyphenyl)-1-[2-(4-fluorophenyl)ethyl]-4-piperidi nemethanol
UA57859C2 (uk)	2003-07-15	СКЛАДНІ ЕФІРИ (+)-АЛЬФА-(2,3-ДИМЕТОКСИФЕНІЛ)-1-[2-(4-ФТОРФЕНІЛ)ЕТИЛ]-4-ПІПЕРИДИНМЕТАНОЛУ, СПОСІБ ЇХ ОТРИМАННЯ, ФАРМАЦЕВТИЧНА КОМПОЗИЦІЯ, СПОСІБ ІНГІБУВАННЯ ДІЇ СЕРОТОНІНУ НА 5HT<sub>2A</sub> РЕЦЕПТОР, СПОСІБ ЛІКУВАННЯ
EP1289527B1 (en)	2008-03-26	(+)-alpha-(2,3-dimethoxyphenyl)-1(2-(4-fluorophenyl)ethyl)-4-piperidinemethanol or its prodrug to treat dementia or cognitive impairment
TW517048B (en)	2003-01-11	Pharmaceutical composition for treating depressive disorders and bipolardisorders comprising (+)-Α-(2,3-dimethoxyphenyl)-1-[2-(4-fluorophenyl)ethyl]-4-piperidinemethanol
AU2001264842A1 (en)	2002-02-21	Use of (+)-alpha -(2,3-dimethoxyphenyl)-1-(2-(4-fluorophenyl)ethyl)-4- piperidinemerthanol or its prodrug in the treatment of symptoms of dementia and dopamine induced psychosis
TW461885B (en)	2001-11-01	Esters of (+)-Α-(2,3-dimethoxyphenyl)-1-[2-(4-fluorophenyl)ethyl]-4-piperidinemethanol
BG65206B1 (bg)	2007-07-31	Естери на (+)-алфа-(2,3-диметоксифенил)-1-[2-(4-флуорoфенил)етил]-4- пиперидинметанол, метод за тяхното получаване и приложението им като предшественици на 5ht2a рецепторния антагонист mdl 110,907
AU2004200993A1 (en)	2004-04-01	Esters of (+)-alpha-(2,3-dimethoxyphenyl-[2-(4-flurophenyl) ethyl]-4-piperidinemethanol and their use as prodrugs of the 5HT2a receptor antagonist MDL 110,907
MXPA01003535A (en)	2002-06-05	Esters of (+)-alpha-( 2,3- dimethoxyphenyl) -1-[2-(4- fluorophenyl) ethyl]-4- piperidinemethanol and their use as prodrugs of the 5ht2a receptor antagonist mdl 110,907
HK1039332B (en)	2005-02-04	Piperidinemethanol and their use as prodrugs of the 5ht2a receptor antagonist mdl 110,907
HU215599B (hu)	1999-01-28	Alfa-(4-klór-fenil)-4-[(4-fluor-fenil)-metil]-piperidin-1-etanol-észter-származékok, eljárás előállításukra és a vegyületeket tartalmazó gyógyszerkészítmények