BE565941A - - Google Patents
Info
- Publication number
- BE565941A BE565941A BE565941DA BE565941A BE 565941 A BE565941 A BE 565941A BE 565941D A BE565941D A BE 565941DA BE 565941 A BE565941 A BE 565941A
- Authority
- BE
- Belgium
- Prior art keywords
- quinoline
- acid
- addition
- crystallizes
- trihydrochloride
- Prior art date
Links
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 50
- 238000002360 preparation method Methods 0.000 claims description 15
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 claims description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 48
- 150000003839 salts Chemical class 0.000 claims 37
- 239000002253 acid Substances 0.000 claims 35
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 33
- 238000000034 method Methods 0.000 claims 27
- 150000001875 compounds Chemical class 0.000 claims 26
- 239000000047 product Substances 0.000 claims 23
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 22
- 125000004432 carbon atom Chemical group C* 0.000 claims 22
- 238000002844 melting Methods 0.000 claims 22
- 230000008018 melting Effects 0.000 claims 22
- 238000000354 decomposition reaction Methods 0.000 claims 21
- 239000000203 mixture Substances 0.000 claims 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 19
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 16
- 239000003795 chemical substances by application Substances 0.000 claims 16
- 125000003545 alkoxy group Chemical group 0.000 claims 14
- 230000000842 anti-protozoal effect Effects 0.000 claims 14
- 239000000243 solution Substances 0.000 claims 14
- 239000003904 antiprotozoal agent Substances 0.000 claims 13
- 239000002585 base Substances 0.000 claims 13
- 238000009835 boiling Methods 0.000 claims 13
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims 12
- -1 benzylsulfonyl Chemical group 0.000 claims 12
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims 11
- 238000010992 reflux Methods 0.000 claims 10
- 239000000825 pharmaceutical preparation Substances 0.000 claims 9
- 238000004519 manufacturing process Methods 0.000 claims 7
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 6
- 150000003248 quinolines Chemical class 0.000 claims 6
- 239000000126 substance Substances 0.000 claims 6
- 150000001338 aliphatic hydrocarbons Chemical group 0.000 claims 5
- 125000000217 alkyl group Chemical group 0.000 claims 5
- GLUUGHFHXGJENI-UHFFFAOYSA-N diethylenediamine Natural products C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 5
- 239000011541 reaction mixture Substances 0.000 claims 5
- 239000007787 solid Substances 0.000 claims 5
- 150000001412 amines Chemical class 0.000 claims 4
- 239000000706 filtrate Substances 0.000 claims 4
- 239000012458 free base Substances 0.000 claims 4
- 239000000155 melt Substances 0.000 claims 4
- XCAAYLUBHIIYOT-UHFFFAOYSA-N quinoline;trihydrochloride Chemical compound Cl.Cl.Cl.N1=CC=CC2=CC=CC=C21 XCAAYLUBHIIYOT-UHFFFAOYSA-N 0.000 claims 4
- 239000003826 tablet Substances 0.000 claims 4
- YGGTVPCTAKYCSQ-UHFFFAOYSA-N 6-methoxyquinolin-8-amine Chemical compound N1=CC=CC2=CC(OC)=CC(N)=C21 YGGTVPCTAKYCSQ-UHFFFAOYSA-N 0.000 claims 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 3
- 241001024304 Mino Species 0.000 claims 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims 3
- 239000011449 brick Substances 0.000 claims 3
- 239000002775 capsule Substances 0.000 claims 3
- 238000004821 distillation Methods 0.000 claims 3
- FPGYTTSMRFMJOF-UHFFFAOYSA-N ethyl 4-(3-chloropropyl)piperazine-1-carboxylate Chemical compound CCOC(=O)N1CCN(CCCCl)CC1 FPGYTTSMRFMJOF-UHFFFAOYSA-N 0.000 claims 3
- 239000000725 suspension Substances 0.000 claims 3
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims 2
- DHCXOJNSYQZFBE-UHFFFAOYSA-N 6-ethoxyquinolin-8-amine Chemical compound N1=CC=CC2=CC(OCC)=CC(N)=C21 DHCXOJNSYQZFBE-UHFFFAOYSA-N 0.000 claims 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims 2
- 229920002472 Starch Polymers 0.000 claims 2
- 238000005903 acid hydrolysis reaction Methods 0.000 claims 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 2
- 239000007864 aqueous solution Substances 0.000 claims 2
- 239000011230 binding agent Substances 0.000 claims 2
- 239000003638 chemical reducing agent Substances 0.000 claims 2
- 238000009833 condensation Methods 0.000 claims 2
- 230000005494 condensation Effects 0.000 claims 2
- 238000001816 cooling Methods 0.000 claims 2
- 238000001704 evaporation Methods 0.000 claims 2
- 230000008020 evaporation Effects 0.000 claims 2
- 238000000605 extraction Methods 0.000 claims 2
- 239000007903 gelatin capsule Substances 0.000 claims 2
- 239000007788 liquid Substances 0.000 claims 2
- 239000012280 lithium aluminium hydride Substances 0.000 claims 2
- 239000000314 lubricant Substances 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims 2
- BTUQCUPQFZHMNS-UHFFFAOYSA-N quinoline;dihydrochloride Chemical compound Cl.Cl.N1=CC=CC2=CC=CC=C21 BTUQCUPQFZHMNS-UHFFFAOYSA-N 0.000 claims 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 2
- 238000001953 recrystallisation Methods 0.000 claims 2
- 239000008107 starch Substances 0.000 claims 2
- 235000019698 starch Nutrition 0.000 claims 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims 2
- 239000008096 xylene Substances 0.000 claims 2
- HUUQNWZMQSLPMX-UHFFFAOYSA-N 1-(2-methylpropyl)piperazine Chemical compound CC(C)CN1CCNCC1 HUUQNWZMQSLPMX-UHFFFAOYSA-N 0.000 claims 1
- WGCYRFWNGRMRJA-UHFFFAOYSA-N 1-ethylpiperazine Chemical compound CCN1CCNCC1 WGCYRFWNGRMRJA-UHFFFAOYSA-N 0.000 claims 1
- MXEXYHQSADSZAK-UHFFFAOYSA-N 1-methylpiperazine;hydrobromide Chemical compound Br.CN1CCNCC1 MXEXYHQSADSZAK-UHFFFAOYSA-N 0.000 claims 1
- WHKWMTXTYKVFLK-UHFFFAOYSA-N 1-propan-2-ylpiperazine Chemical compound CC(C)N1CCNCC1 WHKWMTXTYKVFLK-UHFFFAOYSA-N 0.000 claims 1
- FFRBMBIXVSCUFS-UHFFFAOYSA-N 2,4-dinitro-1-naphthol Chemical compound C1=CC=C2C(O)=C([N+]([O-])=O)C=C([N+]([O-])=O)C2=C1 FFRBMBIXVSCUFS-UHFFFAOYSA-N 0.000 claims 1
- QHTUMQYGZQYEOZ-UHFFFAOYSA-N 2-(4-methylpiperazin-1-yl)ethanol Chemical compound CN1CCN(CCO)CC1 QHTUMQYGZQYEOZ-UHFFFAOYSA-N 0.000 claims 1
- XNMYNYSCEJBRPZ-UHFFFAOYSA-N 2-[(3-butyl-1-isoquinolinyl)oxy]-N,N-dimethylethanamine Chemical compound C1=CC=C2C(OCCN(C)C)=NC(CCCC)=CC2=C1 XNMYNYSCEJBRPZ-UHFFFAOYSA-N 0.000 claims 1
- OVLZCXHCJCDIJB-UHFFFAOYSA-N 2-methoxyhexane Chemical compound CCCCC(C)OC OVLZCXHCJCDIJB-UHFFFAOYSA-N 0.000 claims 1
- AKMIPCJUTXDZKR-UHFFFAOYSA-N 4-chlorobutan-2-ol Chemical compound CC(O)CCCl AKMIPCJUTXDZKR-UHFFFAOYSA-N 0.000 claims 1
- HFDLDPJYCIEXJP-UHFFFAOYSA-N 6-methoxyquinoline Chemical compound N1=CC=CC2=CC(OC)=CC=C21 HFDLDPJYCIEXJP-UHFFFAOYSA-N 0.000 claims 1
- WREVVZMUNPAPOV-UHFFFAOYSA-N 8-aminoquinoline Chemical compound C1=CN=C2C(N)=CC=CC2=C1 WREVVZMUNPAPOV-UHFFFAOYSA-N 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 108010010803 Gelatin Proteins 0.000 claims 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims 1
- MFESCIUQSIBMSM-UHFFFAOYSA-N I-BCP Chemical compound ClCCCBr MFESCIUQSIBMSM-UHFFFAOYSA-N 0.000 claims 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 claims 1
- 241000222722 Leishmania <genus> Species 0.000 claims 1
- 241001465754 Metazoa Species 0.000 claims 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims 1
- 241000669298 Pseudaulacaspis pentagona Species 0.000 claims 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims 1
- 150000007513 acids Chemical class 0.000 claims 1
- 239000012670 alkaline solution Substances 0.000 claims 1
- 229940040526 anhydrous sodium acetate Drugs 0.000 claims 1
- 238000010171 animal model Methods 0.000 claims 1
- 229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 claims 1
- 239000008346 aqueous phase Substances 0.000 claims 1
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 239000007979 citrate buffer Substances 0.000 claims 1
- 239000012141 concentrate Substances 0.000 claims 1
- 239000006071 cream Substances 0.000 claims 1
- 238000002425 crystallisation Methods 0.000 claims 1
- 230000008025 crystallization Effects 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- ZYBWTEQKHIADDQ-UHFFFAOYSA-N ethanol;methanol Chemical compound OC.CCO ZYBWTEQKHIADDQ-UHFFFAOYSA-N 0.000 claims 1
- PBOTXPDTKKNNFI-UHFFFAOYSA-N ethyl 4-butylpiperazine-1-carboxylate Chemical compound CCCCN1CCN(C(=O)OCC)CC1 PBOTXPDTKKNNFI-UHFFFAOYSA-N 0.000 claims 1
- HRMZRPQIFGCXML-UHFFFAOYSA-N ethyl 4-propan-2-ylpiperazine-1-carboxylate Chemical compound CCOC(=O)N1CCN(C(C)C)CC1 HRMZRPQIFGCXML-UHFFFAOYSA-N 0.000 claims 1
- LNOQURRKNJKKBU-UHFFFAOYSA-N ethyl piperazine-1-carboxylate Chemical compound CCOC(=O)N1CCNCC1 LNOQURRKNJKKBU-UHFFFAOYSA-N 0.000 claims 1
- SLKWSZYSOUHYME-UHFFFAOYSA-N ethyl piperazine-1-carboxylate;hydrochloride Chemical compound Cl.CCOC(=O)N1CCNCC1 SLKWSZYSOUHYME-UHFFFAOYSA-N 0.000 claims 1
- 238000001914 filtration Methods 0.000 claims 1
- 238000004508 fractional distillation Methods 0.000 claims 1
- 229920000159 gelatin Polymers 0.000 claims 1
- 239000008273 gelatin Substances 0.000 claims 1
- 235000019322 gelatine Nutrition 0.000 claims 1
- 235000011852 gelatine desserts Nutrition 0.000 claims 1
- 238000005469 granulation Methods 0.000 claims 1
- 230000003179 granulation Effects 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 150000004678 hydrides Chemical class 0.000 claims 1
- PSXRWZBTVAZNSF-UHFFFAOYSA-N hydron;quinoline;chloride Chemical compound Cl.N1=CC=CC2=CC=CC=C21 PSXRWZBTVAZNSF-UHFFFAOYSA-N 0.000 claims 1
- 238000002955 isolation Methods 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 239000008101 lactose Substances 0.000 claims 1
- 231100000053 low toxicity Toxicity 0.000 claims 1
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 claims 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims 1
- VXDQCNRBICUPEY-UHFFFAOYSA-N n-(3-chloropropyl)-6-methoxyquinolin-8-amine Chemical compound N1=CC=CC2=CC(OC)=CC(NCCCCl)=C21 VXDQCNRBICUPEY-UHFFFAOYSA-N 0.000 claims 1
- 239000012071 phase Substances 0.000 claims 1
- 229910000027 potassium carbonate Inorganic materials 0.000 claims 1
- NARVIWMVBMUEOG-UHFFFAOYSA-N prop-1-en-2-ol Chemical compound CC(O)=C NARVIWMVBMUEOG-UHFFFAOYSA-N 0.000 claims 1
- 239000001294 propane Substances 0.000 claims 1
- 239000001632 sodium acetate Substances 0.000 claims 1
- 235000017281 sodium acetate Nutrition 0.000 claims 1
- 238000000638 solvent extraction Methods 0.000 claims 1
- 239000007858 starting material Substances 0.000 claims 1
- 238000003756 stirring Methods 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims 1
- 230000009466 transformation Effects 0.000 claims 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
Classifications
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE565941A true BE565941A (en, 2012) |
Family
ID=186264
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE565941D BE565941A (en, 2012) |
Country Status (1)
| Country | Link |
|---|---|
| BE (1) | BE565941A (en, 2012) |
-
0
- BE BE565941D patent/BE565941A/fr unknown
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