CH639847A5 - Cicloalchiltriazoli. - Google Patents
Cicloalchiltriazoli. Download PDFInfo
- Publication number
- CH639847A5 CH639847A5 CH268579A CH268579A CH639847A5 CH 639847 A5 CH639847 A5 CH 639847A5 CH 268579 A CH268579 A CH 268579A CH 268579 A CH268579 A CH 268579A CH 639847 A5 CH639847 A5 CH 639847A5
- Authority
- CH
- Switzerland
- Prior art keywords
- alch
- piperazinyl
- alcohol
- mol
- solution
- Prior art date
Links
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 74
- 235000019441 ethanol Nutrition 0.000 description 32
- 239000000243 solution Substances 0.000 description 26
- 239000000203 mixture Substances 0.000 description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 17
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 17
- 150000001875 compounds Chemical class 0.000 description 17
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- 238000000034 method Methods 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- 239000000047 product Substances 0.000 description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 239000002253 acid Substances 0.000 description 12
- 239000007787 solid Substances 0.000 description 12
- 239000003814 drug Substances 0.000 description 11
- 229940079593 drug Drugs 0.000 description 10
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 238000011282 treatment Methods 0.000 description 9
- 206010048010 Withdrawal syndrome Diseases 0.000 description 8
- 238000001914 filtration Methods 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 8
- BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 7
- 208000007271 Substance Withdrawal Syndrome Diseases 0.000 description 7
- 150000007513 acids Chemical class 0.000 description 7
- 239000003054 catalyst Substances 0.000 description 7
- 150000003839 salts Chemical class 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 208000024891 symptom Diseases 0.000 description 7
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
- 150000001411 amidrazones Chemical class 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- -1 -OH Chemical group 0.000 description 5
- 206010030043 Ocular hypertension Diseases 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 230000000391 smoking effect Effects 0.000 description 5
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 206010012335 Dependence Diseases 0.000 description 4
- 208000010412 Glaucoma Diseases 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- XYOVOXDWRFGKEX-UHFFFAOYSA-N azepine Chemical compound N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 125000004494 ethyl ester group Chemical group 0.000 description 4
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 229960005181 morphine Drugs 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 206010020772 Hypertension Diseases 0.000 description 3
- 241000283973 Oryctolagus cuniculus Species 0.000 description 3
- 208000028017 Psychotic disease Diseases 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000002671 adjuvant Substances 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 239000003889 eye drop Substances 0.000 description 3
- 229940012356 eye drops Drugs 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 230000001631 hypertensive effect Effects 0.000 description 3
- 231100000252 nontoxic Toxicity 0.000 description 3
- 230000003000 nontoxic effect Effects 0.000 description 3
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 3
- 208000011580 syndromic disease Diseases 0.000 description 3
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 description 2
- YZONATNAFUCUCF-UHFFFAOYSA-N 2-[4-(2,5-dichlorophenyl)piperazin-1-yl]propanoic acid Chemical compound C1CN(C(C)C(O)=O)CCN1C1=CC(Cl)=CC=C1Cl YZONATNAFUCUCF-UHFFFAOYSA-N 0.000 description 2
- VWJSKYGARMKRLR-UHFFFAOYSA-N 2-[4-(2-methylphenyl)piperazin-1-yl]propanoic acid Chemical compound C1CN(C(C)C(O)=O)CCN1C1=CC=CC=C1C VWJSKYGARMKRLR-UHFFFAOYSA-N 0.000 description 2
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 2
- USSIQXCVUWKGNF-UHFFFAOYSA-N 6-(dimethylamino)-4,4-diphenylheptan-3-one Chemical compound C=1C=CC=CC=1C(CC(C)N(C)C)(C(=O)CC)C1=CC=CC=C1 USSIQXCVUWKGNF-UHFFFAOYSA-N 0.000 description 2
- 206010012218 Delirium Diseases 0.000 description 2
- 208000004547 Hallucinations Diseases 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 230000000881 depressing effect Effects 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 229960001797 methadone Drugs 0.000 description 2
- 230000003533 narcotic effect Effects 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
- 238000007911 parenteral administration Methods 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 230000008288 physiological mechanism Effects 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000000698 schizophrenic effect Effects 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- QCHFTSOMWOSFHM-WPRPVWTQSA-N (+)-Pilocarpine Chemical compound C1OC(=O)[C@@H](CC)[C@H]1CC1=CN=CN1C QCHFTSOMWOSFHM-WPRPVWTQSA-N 0.000 description 1
- KWTSXDURSIMDCE-QMMMGPOBSA-N (S)-amphetamine Chemical compound C[C@H](N)CC1=CC=CC=C1 KWTSXDURSIMDCE-QMMMGPOBSA-N 0.000 description 1
- PJCRARZGAHXJHN-UHFFFAOYSA-N 2,3,4,5-tetrahydropyridin-6-ylhydrazine Chemical compound NNC1=NCCCC1 PJCRARZGAHXJHN-UHFFFAOYSA-N 0.000 description 1
- CGKMTWOCMVOOGV-UHFFFAOYSA-N 2-[4-(2-methylphenyl)piperazin-1-yl]propanehydrazide Chemical compound C1(=C(C=CC=C1)N1CCN(CC1)C(C(=O)NN)C)C CGKMTWOCMVOOGV-UHFFFAOYSA-N 0.000 description 1
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 1
- FJCXXLZGBXLQNN-UHFFFAOYSA-N 2-piperazin-1-ylpropanenitrile Chemical compound N#CC(C)N1CCNCC1 FJCXXLZGBXLQNN-UHFFFAOYSA-N 0.000 description 1
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 1
- 208000028048 Accommodation disease Diseases 0.000 description 1
- 206010001497 Agitation 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
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- GJSURZIOUXUGAL-UHFFFAOYSA-N Clonidine Chemical compound ClC1=CC=CC(Cl)=C1NC1=NCCN1 GJSURZIOUXUGAL-UHFFFAOYSA-N 0.000 description 1
- 206010010904 Convulsion Diseases 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 206010027646 Miosis Diseases 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 206010049816 Muscle tightness Diseases 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 241000220304 Prunus dulcis Species 0.000 description 1
- QCHFTSOMWOSFHM-UHFFFAOYSA-N SJ000285536 Natural products C1OC(=O)C(CC)C1CC1=CN=CN1C QCHFTSOMWOSFHM-UHFFFAOYSA-N 0.000 description 1
- 208000013738 Sleep Initiation and Maintenance disease Diseases 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 101100054666 Streptomyces halstedii sch3 gene Proteins 0.000 description 1
- 206010044565 Tremor Diseases 0.000 description 1
- 230000006978 adaptation Effects 0.000 description 1
- 235000020224 almond Nutrition 0.000 description 1
- 229940025084 amphetamine Drugs 0.000 description 1
- 229940035676 analgesics Drugs 0.000 description 1
- 239000000730 antalgic agent Substances 0.000 description 1
- 230000001384 anti-glaucoma Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- UREBDLICKHMUKA-DVTGEIKXSA-N betamethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O UREBDLICKHMUKA-DVTGEIKXSA-N 0.000 description 1
- 229960002537 betamethasone Drugs 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 206010007776 catatonia Diseases 0.000 description 1
- 229910052801 chlorine Inorganic materials 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
- 229960002896 clonidine Drugs 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000036461 convulsion Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 206010013663 drug dependence Diseases 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- DZGCGKFAPXFTNM-UHFFFAOYSA-N ethanol;hydron;chloride Chemical compound Cl.CCO DZGCGKFAPXFTNM-UHFFFAOYSA-N 0.000 description 1
- AEOCXXJPGCBFJA-UHFFFAOYSA-N ethionamide Chemical compound CCC1=CC(C(N)=S)=CC=N1 AEOCXXJPGCBFJA-UHFFFAOYSA-N 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- QMEZUZOCLYUADC-UHFFFAOYSA-N hydrate;dihydrochloride Chemical compound O.Cl.Cl QMEZUZOCLYUADC-UHFFFAOYSA-N 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 206010022437 insomnia Diseases 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000009533 lab test Methods 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical group C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 230000003547 miosis Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000002969 morbid Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 229940124641 pain reliever Drugs 0.000 description 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- 230000010254 physiological adaptation Effects 0.000 description 1
- 229960001416 pilocarpine Drugs 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000001671 psychotherapy Methods 0.000 description 1
- NWELCUKYUCBVKK-UHFFFAOYSA-N pyridin-2-ylhydrazine Chemical compound NNC1=CC=CC=N1 NWELCUKYUCBVKK-UHFFFAOYSA-N 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000009256 replacement therapy Methods 0.000 description 1
- 201000000980 schizophrenia Diseases 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 208000011117 substance-related disease Diseases 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 150000003852 triazoles Chemical group 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/14—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D295/145—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/15—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- 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
- A61P25/30—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
- A61P27/00—Drugs for disorders of the senses
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A61P27/06—Antiglaucoma agents or miotics
-
- 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
- C07D211/68—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 one double bond between ring members or between a ring member and a non-ring member
- C07D211/72—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 one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Ophthalmology & Optometry (AREA)
- Psychiatry (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Addiction (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT22421/78A IT1094076B (it) | 1978-04-18 | 1978-04-18 | Cicloalchiltriazoli |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH639847A5 true CH639847A5 (it) | 1983-12-15 |
Family
ID=11196066
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH268579A CH639847A5 (it) | 1978-04-18 | 1979-03-22 | Cicloalchiltriazoli. |
Country Status (22)
| Country | Link |
|---|---|
| US (2) | US4252721A (en, 2012) |
| JP (1) | JPS5817757B2 (en, 2012) |
| AT (1) | AT374477B (en, 2012) |
| AU (1) | AU520788B2 (en, 2012) |
| BG (2) | BG40654A3 (en, 2012) |
| CA (1) | CA1104567A (en, 2012) |
| CH (1) | CH639847A5 (en, 2012) |
| DE (1) | DE2915318A1 (en, 2012) |
| DK (1) | DK148480C (en, 2012) |
| FI (1) | FI66378C (en, 2012) |
| FR (1) | FR2423221A1 (en, 2012) |
| GB (1) | GB2020269B (en, 2012) |
| HU (1) | HU179917B (en, 2012) |
| IE (1) | IE47965B1 (en, 2012) |
| IL (1) | IL56926A (en, 2012) |
| IT (1) | IT1094076B (en, 2012) |
| NL (1) | NL186635C (en, 2012) |
| PL (1) | PL116103B1 (en, 2012) |
| PT (1) | PT69502A (en, 2012) |
| SE (1) | SE437663B (en, 2012) |
| SU (1) | SU852174A3 (en, 2012) |
| YU (1) | YU41338B (en, 2012) |
Families Citing this family (45)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1248531A (en) * | 1984-04-17 | 1989-01-10 | Jeffrey C. Watkins | 4-substituted piperazine-2-carboxylic acids |
| FR2580648B1 (fr) * | 1985-04-17 | 1987-05-15 | Adir | Nouveaux derives du triazole, leur procede de preparation et les compositions pharmaceutiques les renfermant |
| US4879294A (en) * | 1988-01-28 | 1989-11-07 | Angelini Pharmaceuticals Ltd. | Opthalmic composition |
| IT1224250B (it) * | 1988-06-10 | 1990-09-26 | Acraf | Associzione del depiprazolo con la morfina |
| IT1250701B (it) | 1991-07-24 | 1995-04-21 | Angelini Francesco Ist Ricerca | Composizione farmaceutica solida per uso orale a base di dapiprazolo |
| US5288759A (en) * | 1992-08-27 | 1994-02-22 | Alcon Laboratories, Inc. | Use of certain sulfamoyl-substituted phenethylamine derivatives to reverse drug-induced mydriasis |
| US6187774B1 (en) | 1996-03-04 | 2001-02-13 | Yoshitomi Pharmaceutical Industries, Ltd. | Fused heterocyclic compounds and pharmaceutical applications thereof |
| EP1118322A4 (en) | 1998-09-30 | 2004-10-20 | Takeda Chemical Industries Ltd | MEDICINES THAT IMPROVE BLADDER DRAINING POWER |
| IL141235A (en) * | 2000-02-09 | 2012-04-30 | Novartis Int Pharm Ltd | Combined use of an alpha-adrenoceptor antagonist and a muscarinic antagonist in the preparation of a drug for the treatment of non-malignant prostatic hyperplasia |
| US6730691B1 (en) | 2000-02-10 | 2004-05-04 | Miles A. Galin | Uses of alpha adrenergic blocking agents |
| US20020065286A1 (en) * | 2000-08-21 | 2002-05-30 | Davies Michael John | Treatment of wounds |
| US20020091129A1 (en) * | 2000-11-20 | 2002-07-11 | Mitradev Boolell | Treatment of premature ejaculation |
| WO2003004058A1 (en) * | 2001-07-02 | 2003-01-16 | Santen Pharmaceutical Co., Ltd. | OPTIC NERVE PROTECTING AGENTS CONTAINING α1 RECEPTOR BLOCKER AS THE ACTIVE INGREDIENT |
| GB0130219D0 (en) * | 2001-12-18 | 2002-02-06 | Pfizer Ltd | Compounds for the treatment of sexual dysfunction |
| US20030229001A1 (en) * | 2002-01-31 | 2003-12-11 | Pfizer Inc. | Treatment of male sexual dysfunction |
| DE60336485D1 (de) | 2002-08-19 | 2011-05-05 | Pfizer | Kombinationstherapie gegen hyperproliferative erkrankungen |
| GB0219961D0 (en) | 2002-08-28 | 2002-10-02 | Pfizer Ltd | Oxytocin inhibitors |
| US7323462B2 (en) * | 2002-12-10 | 2008-01-29 | Pfizer Inc. | Morpholine dopamine agonists |
| CA2451267A1 (en) * | 2002-12-13 | 2004-06-13 | Warner-Lambert Company Llc | Pharmaceutical uses for alpha2delta ligands |
| PA8597401A1 (es) * | 2003-03-14 | 2005-05-24 | Pfizer | Derivados del acido 3-(1-[3-(1,3-benzotiazol-6-il) propilcarbamoil] cicloalquil) propanoico como inhibidores de nep |
| US20040220186A1 (en) * | 2003-04-30 | 2004-11-04 | Pfizer Inc. | PDE9 inhibitors for treating type 2 diabetes,metabolic syndrome, and cardiovascular disease |
| US7923467B2 (en) * | 2003-05-30 | 2011-04-12 | Ranbaxy Laboratories, Inc. | Substituted pyrrole derivatives and their use as HMG-CO inhibitors |
| US20050065158A1 (en) * | 2003-07-16 | 2005-03-24 | Pfizer Inc. | Treatment of sexual dysfunction |
| US20050037063A1 (en) * | 2003-07-21 | 2005-02-17 | Bolton Anthony E. | Combined therapies |
| US7291640B2 (en) * | 2003-09-22 | 2007-11-06 | Pfizer Inc. | Substituted triazole derivatives as oxytocin antagonists |
| US20050267096A1 (en) * | 2004-05-26 | 2005-12-01 | Pfizer Inc | New indazole and indolone derivatives and their use pharmaceuticals |
| US20050288270A1 (en) * | 2004-05-27 | 2005-12-29 | Pfizer Inc | New aminopyridine derivatives and their use as pharmaceuticals |
| US7618972B2 (en) * | 2005-03-21 | 2009-11-17 | Pfizer Inc | Substituted triazole derivatives as oxytocin antagonists |
| EP1863484A1 (en) * | 2005-03-21 | 2007-12-12 | Pfizer Limited | Substituted triazole derivatives as oxytocin antagonists |
| WO2007017752A1 (en) * | 2005-08-10 | 2007-02-15 | Pfizer Limited | Substituted triazole derivatives as oxytocin antagonists |
| GT200600381A (es) | 2005-08-25 | 2007-03-28 | Compuestos organicos | |
| US7741317B2 (en) | 2005-10-21 | 2010-06-22 | Bristol-Myers Squibb Company | LXR modulators |
| US8026377B2 (en) * | 2005-11-08 | 2011-09-27 | Ranbaxy Laboratories, Limited | Process for (3R, 5R)-7-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-[(4-hydroxy methyl phenyl amino) carbonyl]-pyrrol-1-yl]-3,5-dihydroxy-heptanoic acid hemi calcium salt |
| US7888376B2 (en) | 2005-11-23 | 2011-02-15 | Bristol-Myers Squibb Company | Heterocyclic CETP inhibitors |
| US7919506B2 (en) | 2006-03-10 | 2011-04-05 | Pfizer Inc. | Dibenzyl amine compounds and derivatives |
| US8383660B2 (en) | 2006-03-10 | 2013-02-26 | Pfizer Inc. | Dibenzyl amine compounds and derivatives |
| WO2008020314A2 (en) * | 2006-03-14 | 2008-02-21 | Ranbaxy Laboratories Limited | Statin stabilizing dosage formulations |
| WO2008010087A2 (en) * | 2006-07-14 | 2008-01-24 | Ranbaxy Laboratories Limited | Polymorphic forms of an hmg-coa reductase inhibitor and uses thereof |
| WO2008070496A2 (en) | 2006-12-01 | 2008-06-12 | Bristol-Myers Squibb Company | N- ( (3-benzyl) -2, 2- (bis-phenyl) -propan-1-amine derivatives as cetp inhibitors for the treatment of atherosclerosis and cardiovascular diseases |
| AU2014255381A1 (en) | 2013-04-17 | 2015-10-08 | Pfizer Inc. | N-piperidin-3-ylbenzamide derivatives for treating cardiovascular diseases |
| WO2016055901A1 (en) | 2014-10-08 | 2016-04-14 | Pfizer Inc. | Substituted amide compounds |
| WO2020081562A1 (en) | 2018-10-15 | 2020-04-23 | Ocuphire Pharma, Inc. | Methods and compositions for treatment of glaucoma and related conditions |
| JP7670945B2 (ja) | 2018-10-26 | 2025-05-01 | オーパス・ジェネティクス・インコーポレイテッド | 老眼、散瞳、および他の眼障害の治療のための方法および組成物 |
| CN113574055B (zh) | 2019-01-18 | 2024-07-23 | 阿斯利康(瑞典)有限公司 | Pcsk9抑制剂及其使用方法 |
| CN115368310B (zh) | 2021-05-18 | 2025-06-27 | 奥库菲尔医药公司 | 合成甲磺酸酚妥拉明的方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2913454A (en) * | 1956-11-23 | 1959-11-17 | Schenley Ind Inc | Certain cycloalkanotriazoles, process and intermediates |
| IT1066857B (it) * | 1965-12-15 | 1985-03-12 | Acraf | Derivati della s ipiazolo 4.3 a piridina e processi per la loro preparazione |
| US3472853A (en) * | 1967-05-29 | 1969-10-14 | Sterling Drug Inc | 1-((pyrido(2,1-c)-s-triazolyl)-lower-alkyl)-4-substituted- piperazines |
| JPS5070389A (en, 2012) * | 1973-10-30 | 1975-06-11 |
-
1978
- 1978-04-18 IT IT22421/78A patent/IT1094076B/it active Protection Beyond IP Right Term
-
1979
- 1979-03-22 CH CH268579A patent/CH639847A5/it not_active IP Right Cessation
- 1979-03-22 IL IL56926A patent/IL56926A/xx unknown
- 1979-03-29 US US06/025,273 patent/US4252721A/en not_active Expired - Lifetime
- 1979-03-30 NL NLAANVRAGE7902489,A patent/NL186635C/xx not_active IP Right Cessation
- 1979-04-09 AU AU45832/79A patent/AU520788B2/en not_active Ceased
- 1979-04-11 FR FR7909229A patent/FR2423221A1/fr active Granted
- 1979-04-11 YU YU862/79A patent/YU41338B/xx unknown
- 1979-04-11 GB GB7912875A patent/GB2020269B/en not_active Expired
- 1979-04-12 FI FI791217A patent/FI66378C/fi not_active IP Right Cessation
- 1979-04-14 DE DE19792915318 patent/DE2915318A1/de active Granted
- 1979-04-17 SE SE7903327A patent/SE437663B/sv not_active IP Right Cessation
- 1979-04-17 PT PT69502A patent/PT69502A/pt unknown
- 1979-04-17 SU SU792753553A patent/SU852174A3/ru active
- 1979-04-17 DK DK156779A patent/DK148480C/da not_active IP Right Cessation
- 1979-04-17 HU HU79AI284A patent/HU179917B/hu unknown
- 1979-04-17 CA CA325,782A patent/CA1104567A/en not_active Expired
- 1979-04-18 PL PL1979214969A patent/PL116103B1/pl unknown
- 1979-04-18 AT AT0292479A patent/AT374477B/de not_active IP Right Cessation
- 1979-04-18 BG BG043291A patent/BG40654A3/xx unknown
- 1979-04-18 JP JP54048519A patent/JPS5817757B2/ja not_active Expired
- 1979-08-08 IE IE646/79A patent/IE47965B1/en not_active IP Right Cessation
-
1980
- 1980-08-29 US US06/182,426 patent/US4307095A/en not_active Expired - Lifetime
-
1994
- 1994-02-25 BG BG098586A patent/BG61367B2/bg unknown
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CH639847A5 (it) | Cicloalchiltriazoli. | |
| PT1877390E (pt) | Compostos benzisoxazole-piridina e métodos para a sua utilização | |
| US5358953A (en) | Imidazopyridine PAF/H1 antagonists | |
| CS247073B2 (en) | Production method of 2-substituted 4-amino-6,7-dimethoxyghinolins | |
| KR20010087361A (ko) | [1,2,4]트리아졸로[1,5-ｃ]피리미딘 유도체 | |
| WO2016148232A1 (ja) | モルヒナン誘導体 | |
| JP7695232B2 (ja) | ヘテロアリール血漿カリクレインインヒビター | |
| WO2018052114A1 (ja) | モルヒナン誘導体のオピオイドδ受容体アゴニスト関連疾患の治療のための使用 | |
| KR20100031610A (ko) | 아데노신 Ａ3 수용체 리간드로서의 트리아졸로[1,5-ａ]퀴놀린 | |
| JPH11508920A (ja) | ２，７―置換オクタヒドロ―ピロロ［１，２―ａ］ピラジン誘導体 | |
| BG103370A (bg) | 2-метоксифенилпиперазинови производни | |
| EP1440075B1 (fr) | Nouveaux derives amides heteroaromatiques de 3beta-amino azabicyclooctane, leur procede de preparation et leurs applications en therapeutique | |
| JPS6231719B2 (en, 2012) | ||
| CS259516B2 (en) | Method of new heterocyclic compounds production | |
| US4325952A (en) | Method of treating abstinence syndrome with cycloaklyltriazoles | |
| HU194228B (en) | Process for production of new, in 11-position substituated 5,11-dihydro-6h-pirido /2,3-b//1,4/-benzodiozepin-6-on and medical compounds containing thereof | |
| US4716166A (en) | Histamine H1 antagonists | |
| US4307096A (en) | Method of treating glaucoma with cycloalkyltriazoles | |
| US20240391941A1 (en) | Naphthyridinone derivatives for the treatment of a disease or disorder | |
| KR100826304B1 (ko) | 피롤로[2,1-ｂ][1,3]벤조티아제핀 및 정신병 치료 활성을갖는 약제의 제조를 위한 그의 용도 | |
| KR820001450B1 (ko) | 사이클로알킬 트리아졸의 제조방법 | |
| JP2025124882A (ja) | ヘテロアリール血漿カリクレインインヒビター | |
| WO2023158725A1 (en) | Adenosine ligands for the treatment of neurological disorders | |
| PT100223B (pt) | Processo para a preparacao de imidazopiridinas antagonistas de paf/h1 | |
| PT94147A (pt) | Processo para preparacao de derivados de tiazepina ede composicoes farmaceuticas que os contem |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |