IL22513A - Quinoline derivatives - Google Patents

Quinoline derivatives

Info

Publication number: IL22513A
Authority: IL; Israel
Prior art keywords: formula; quinoline; quinoline derivatives; acid addition; preparation
Prior art date: 1963-11-26

Application number

IL22513A

Other languages

English (en)

Original Assignee

Rhone Poulenc Sa

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.)

1963-11-26

Filing date

1964-11-25

Publication date

1968-01-25

1964-11-25 Application filed by Rhone Poulenc Sa filed Critical Rhone Poulenc Sa

1968-01-25 Publication of IL22513A publication Critical patent/IL22513A/en

Links

229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 title claims description 15
125000002943 quinolinyl group Chemical class N1=C(C=CC2=CC=CC=C12)* 0.000 title claims description 3
239000002253 acid Substances 0.000 claims description 17
150000003248 quinolines Chemical class 0.000 claims description 16
-1 3- diethylaminomethyl-4-hydroxyphenyl Chemical group 0.000 claims description 15
150000003839 salts Chemical class 0.000 claims description 14
238000000034 method Methods 0.000 claims description 12
238000002360 preparation method Methods 0.000 claims description 9
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 8
238000006243 chemical reaction Methods 0.000 claims description 7
SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Natural products N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 6
231100000252 nontoxic Toxicity 0.000 claims description 5
230000003000 nontoxic effect Effects 0.000 claims description 5
239000003960 organic solvent Substances 0.000 claims description 5
125000004432 carbon atom Chemical group C* 0.000 claims description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
150000004885 piperazines Chemical class 0.000 claims description 4
239000004480 active ingredient Substances 0.000 claims description 3
239000011230 binding agent Substances 0.000 claims description 3
125000005843 halogen group Chemical group 0.000 claims description 3
239000008194 pharmaceutical composition Substances 0.000 claims description 3
125000000217 alkyl group Chemical group 0.000 claims description 2
125000002947 alkylene group Chemical group 0.000 claims description 2
125000004429 atom Chemical group 0.000 claims description 2
238000000576 coating method Methods 0.000 claims description 2
239000003937 drug carrier Substances 0.000 claims description 2
150000002148 esters Chemical class 0.000 claims description 2
229910052736 halogen Inorganic materials 0.000 claims description 2
150000002367 halogens Chemical class 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
239000008016 pharmaceutical coating Substances 0.000 claims description 2
150000002989 phenols Chemical class 0.000 claims description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
125000001246 bromo group Chemical group Br* 0.000 claims 1
229910052801 chlorine Inorganic materials 0.000 claims 1
239000000460 chlorine Substances 0.000 claims 1
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 1
239000000203 mixture Substances 0.000 description 11
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
239000002585 base Substances 0.000 description 5
150000001875 compounds Chemical class 0.000 description 5
239000002904 solvent Substances 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
239000003701 inert diluent Substances 0.000 description 4
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
239000000243 solution Substances 0.000 description 4
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
239000013543 active substance Substances 0.000 description 3
150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
238000009835 boiling Methods 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
150000002576 ketones Chemical class 0.000 description 3
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
239000008247 solid mixture Substances 0.000 description 3
238000009736 wetting Methods 0.000 description 3
239000000080 wetting agent Substances 0.000 description 3
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
229920002472 Starch Polymers 0.000 description 2
239000002671 adjuvant Substances 0.000 description 2
150000001450 anions Chemical class 0.000 description 2
239000000839 emulsion Substances 0.000 description 2
238000001914 filtration Methods 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
235000019359 magnesium stearate Nutrition 0.000 description 2
239000003921 oil Substances 0.000 description 2
235000019198 oils Nutrition 0.000 description 2
239000000546 pharmaceutical excipient Substances 0.000 description 2
229940075930 picrate Drugs 0.000 description 2
OXNIZHLAWKMVMX-UHFFFAOYSA-M picrate anion Chemical compound [O-]C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-M 0.000 description 2
239000003755 preservative agent Substances 0.000 description 2
239000000725 suspension Substances 0.000 description 2
239000003765 sweetening agent Substances 0.000 description 2
230000001225 therapeutic effect Effects 0.000 description 2
HSKBGALULOFBAM-UHFFFAOYSA-N 2,3-dihydroxy-4-methylidene-3h-naphthalene-1-carboxylic acid Chemical class C1=CC=C2C(=C)C(O)C(O)=C(C(O)=O)C2=C1 HSKBGALULOFBAM-UHFFFAOYSA-N 0.000 description 1
WXTMDXOMEHJXQO-UHFFFAOYSA-N 2,5-dihydroxybenzoic acid Chemical class OC(=O)C1=CC(O)=CC=C1O WXTMDXOMEHJXQO-UHFFFAOYSA-N 0.000 description 1
OGMCDNXCHXQKHO-UHFFFAOYSA-N 4-(2-iodoethyl)phenol Chemical compound OC1=CC=C(CCI)C=C1 OGMCDNXCHXQKHO-UHFFFAOYSA-N 0.000 description 1
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
239000002202 Polyethylene glycol Substances 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical class CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
229930006000 Sucrose Natural products 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
244000299461 Theobroma cacao Species 0.000 description 1
235000005764 Theobroma cacao ssp. cacao Nutrition 0.000 description 1
235000005767 Theobroma cacao ssp. sphaerocarpum Nutrition 0.000 description 1
241000209140 Triticum Species 0.000 description 1
235000021307 Triticum Nutrition 0.000 description 1
150000001242 acetic acid derivatives Chemical class 0.000 description 1
239000000783 alginic acid Substances 0.000 description 1
235000010443 alginic acid Nutrition 0.000 description 1
229920000615 alginic acid Polymers 0.000 description 1
229960001126 alginic acid Drugs 0.000 description 1
150000004781 alginic acids Chemical class 0.000 description 1
150000001339 alkali metal compounds Chemical class 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
229940124323 amoebicide Drugs 0.000 description 1
230000000507 anthelmentic effect Effects 0.000 description 1
229940124339 anthelmintic agent Drugs 0.000 description 1
239000000921 anthelmintic agent Substances 0.000 description 1
239000003430 antimalarial agent Substances 0.000 description 1
229940033495 antimalarials Drugs 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
239000003125 aqueous solvent Substances 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
150000001558 benzoic acid derivatives Chemical class 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
235000014121 butter Nutrition 0.000 description 1
235000001046 cacaotero Nutrition 0.000 description 1
235000010216 calcium carbonate Nutrition 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
239000002775 capsule Substances 0.000 description 1
230000000973 chemotherapeutic effect Effects 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
239000008119 colloidal silica Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
238000010908 decantation Methods 0.000 description 1
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
230000001804 emulsifying effect Effects 0.000 description 1
LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 description 1
229940093471 ethyl oleate Drugs 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
239000008187 granular material Substances 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
238000010348 incorporation Methods 0.000 description 1
239000008101 lactose Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
229940057995 liquid paraffin Drugs 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
150000002688 maleic acid derivatives Chemical class 0.000 description 1
239000000463 material Substances 0.000 description 1
150000002823 nitrates Chemical class 0.000 description 1
239000012457 nonaqueous media Substances 0.000 description 1
235000008390 olive oil Nutrition 0.000 description 1
239000004006 olive oil Substances 0.000 description 1
150000002895 organic esters Chemical class 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
150000003891 oxalate salts Chemical class 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
239000002304 perfume Substances 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
230000001766 physiological effect Effects 0.000 description 1
239000006187 pill Substances 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229920001592 potato starch Polymers 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
230000000069 prophylactic effect Effects 0.000 description 1
239000000376 reactant Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
150000003873 salicylate salts Chemical class 0.000 description 1
235000009518 sodium iodide Nutrition 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000008223 sterile water Substances 0.000 description 1
230000001954 sterilising effect Effects 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
150000003890 succinate salts Chemical class 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
238000011287 therapeutic dose Methods 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
238000010792 warming Methods 0.000 description 1
239000001993 wax Substances 0.000 description 1
229940100445 wheat starch Drugs 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
- C07D295/12—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 singly or doubly bound nitrogen atoms
- C07D295/135—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 singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/38—Nitrogen atoms
- C07D215/42—Nitrogen atoms attached in position 4
- C07D215/46—Nitrogen atoms attached in position 4 with hydrocarbon radicals, substituted by nitrogen atoms, attached to said nitrogen atoms
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S424/00—Drug, bio-affecting and body treating compositions
- Y10S424/04—Dandruff

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical 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)

IL22513A 1963-11-26 1964-11-25 Quinoline derivatives IL22513A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
FR955044A FR1427630A (fr)	1963-11-26	1963-11-26	Nouveaux dérivés de la quinoléine et leur préparation

Publications (1)

Publication Number	Publication Date
IL22513A true IL22513A (en)	1968-01-25

Family

ID=8817424

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL22513A IL22513A (en)	1963-11-26	1964-11-25	Quinoline derivatives

Country Status (10)

Country	Link
US (1)	US3324129A (fr)
AT (1)	AT254190B (fr)
BE (1)	BE656240A (fr)
CH (1)	CH423779A (fr)
ES (1)	ES306443A1 (fr)
FR (1)	FR1427630A (fr)
GB (1)	GB1021950A (fr)
IL (1)	IL22513A (fr)
LU (1)	LU47439A1 (fr)
NL (1)	NL6413687A (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB8424979D0 (en) *	1984-10-03	1984-11-07	Wyeth John & Brother Ltd	Benzenesulphonamide derivatives
EP2379505A4 (fr) *	2008-12-05	2012-10-17	Designmedix Inc	Chloroquines modifiées par un groupement monocyclique ou un groupement à cycles fusionnés

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3126384A (en) *	1961-05-26	1964-03-24		X-quinolyl-aminoalkylamino
US3101338A (en) *	1962-09-06	1963-08-20	Searle & Co	Hydroxydialkylaminoalkylaminoisoquinolines and related compounds
FR86513E (fr) *	1963-03-25	1966-02-25	Rhone Poulenc Sa	Nouveaux dérivés de la quinoléine et leur préparation

1963
- 1963-11-26 FR FR955044A patent/FR1427630A/fr not_active Expired
1964
- 1964-11-12 US US411678A patent/US3324129A/en not_active Expired - Lifetime
- 1964-11-16 AT AT967864A patent/AT254190B/de active
- 1964-11-18 GB GB47019/64A patent/GB1021950A/en not_active Expired
- 1964-11-25 NL NL6413687A patent/NL6413687A/xx unknown
- 1964-11-25 BE BE656240A patent/BE656240A/xx unknown
- 1964-11-25 LU LU47439A patent/LU47439A1/xx unknown
- 1964-11-25 IL IL22513A patent/IL22513A/en unknown
- 1964-11-26 CH CH1527964A patent/CH423779A/fr unknown
- 1964-11-26 ES ES0306443A patent/ES306443A1/es not_active Expired

Also Published As

Publication number	Publication date
AT254190B (de)	1967-05-10
ES306443A1 (es)	1965-02-16
GB1021950A (en)	1966-03-09
NL6413687A (fr)	1965-05-27
FR1427630A (fr)	1966-02-11
BE656240A (fr)	1965-05-25
LU47439A1 (fr)	1965-01-26
US3324129A (en)	1967-06-06
CH423779A (fr)	1966-11-15

Publication	Publication Date	Title
JP2608788B2 (ja)	1997-05-14	精神分裂病治療剤
HU211682A9 (en)	1995-12-28	10,11-methanodibenzosuberane derivatives
US4234585A (en)	1980-11-18	1,2-Dihydroquinoline-2-one derivatives
FI85269C (fi)	1992-03-25	Foerfarande foer framstaellning av terapeutiskt anvaendbara kumarinderivat.
DK159114B (da)	1990-09-03	Benzyldihydrofuropyridinderivater og praeparater indeholdende disse forbindelser
DK158836B (da)	1990-07-23	Analogifremgangsmaade til fremstilling af terapeutisk aktive anthraquinonderivater
US3257404A (en)	1966-06-21	Piperazine derivatives of dibenzo[a,d] cycloheptadiene
JPH0473432B2 (fr)	1992-11-20
US3173918A (en)	1965-03-16	Bis(x-quwolyl-piperazinyjl) compounds
US4001271A (en)	1977-01-04	3-(isopropyl amino alkoxy)-2-phenyl-isoindolin-1-ones
EP0061149A1 (fr)	1982-09-29	Dérivés du alkylènedioxybenzène et leurs sels d'addition acides et procédé pour leur préparation
US3324129A (en)	1967-06-06	Quinoline derivatives
US3822269A (en)	1974-07-02	6-aminoalkylamino-hexahydrophenanthridines useful as antiarrhythmic agents
JPH07503000A (ja)	1995-03-30	Ｃｎｓ活性を示すトラゾドンのアルキル誘導体
US3970757A (en)	1976-07-20	Tetrahydro-carbazole derivatives as gastric anti-secretory agents
EP0161498B1 (fr)	1988-10-12	Dérivés de la phénylpipérazine et leur sels d'addition acides
US4252806A (en)	1981-02-24	Triazoloquinolones
US3325497A (en)	1967-06-13	Cycloheptatrienylpiperazines
US4254124A (en)	1981-03-03	Antidepressant agent
EP0505481A1 (fr)	1992-09-30	4,5-diphenyle-imidazoles substituees en position 2
EP0024638A1 (fr)	1981-03-11	Acides quinoléinone alkylcarboxyliques substitués, leur préparation et médicaments les contenant
US3959476A (en)	1976-05-25	Antihypertensive substituted triazoles
US3196155A (en)	1965-07-20	Bis(quinolylaminoalkyl)piperazines
NZ205469A (en)	1986-04-11	Sulfamoylbenzophenone derivatives and pharmaceutical compositions
US4000306A (en)	1976-12-28	Anti-arrhythmic compositions containing isoindoline derivatives