SK97787A3 - Indolizine derivatives, process for their preparation and pharmaceutical or verinary composition containing them - Google Patents

Indolizine derivatives, process for their preparation and pharmaceutical or verinary composition containing them Download PDF

Info

Publication number: SK97787A3
Authority: SK; Slovakia
Prior art keywords: indolizine; methyl; pharmaceutically acceptable; ethyl; benzenesulfonyl
Prior art date: 1986-02-14

Application number

SK977-87A

Other languages

English (en)

Slovak (sk)

Other versions

SK279557B6 (sk

Inventor

Jean Gubin

Pierre Chatelain

Marcel Descamps

Dino Nisato

Original Assignee

Sanofi 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.)

1986-02-14

Filing date

1987-02-13

Publication date

1998-12-02

1987-02-13 Application filed by Sanofi Sa filed Critical Sanofi Sa

1998-12-02 Publication of SK279557B6 publication Critical patent/SK279557B6/sk

1998-12-02 Publication of SK97787A3 publication Critical patent/SK97787A3/sk

Links

238000000034 method Methods 0.000 title claims description 35
239000000203 mixture Substances 0.000 title claims description 28
230000008569 process Effects 0.000 title claims description 25
238000002360 preparation method Methods 0.000 title claims description 17
125000003406 indolizinyl group Chemical class C=1(C=CN2C=CC=CC12)* 0.000 title abstract 2
-1 2,3-methylenedioxyphenyl Chemical group 0.000 claims abstract description 65
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 23
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 20
239000001257 hydrogen Substances 0.000 claims abstract description 19
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 19
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 15
NARVIWMVBMUEOG-UHFFFAOYSA-N 2-Hydroxy-propylene Natural products CC(O)=C NARVIWMVBMUEOG-UHFFFAOYSA-N 0.000 claims abstract description 12
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 10
125000000217 alkyl group Chemical group 0.000 claims abstract description 9
150000002431 hydrogen Chemical class 0.000 claims abstract description 9
125000002947 alkylene group Chemical group 0.000 claims abstract description 6
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 5
208000011580 syndromic disease Diseases 0.000 claims abstract description 5
230000001575 pathological effect Effects 0.000 claims abstract description 4
229910052736 halogen Inorganic materials 0.000 claims abstract 2
150000002367 halogens Chemical class 0.000 claims abstract 2
150000001875 compounds Chemical class 0.000 claims description 99
150000002478 indolizines Chemical class 0.000 claims description 26
150000003839 salts Chemical class 0.000 claims description 26
125000004432 carbon atom Chemical group C* 0.000 claims description 23
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 23
239000007858 starting material Substances 0.000 claims description 20
125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 17
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 15
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 14
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 13
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 13
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 12
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 12
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 12
239000004480 active ingredient Substances 0.000 claims description 10
HOBCFUWDNJPFHB-UHFFFAOYSA-N indolizine Chemical compound C1=CC=CN2C=CC=C21 HOBCFUWDNJPFHB-UHFFFAOYSA-N 0.000 claims description 10
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 10
125000004193 piperazinyl group Chemical group 0.000 claims description 10
239000002904 solvent Substances 0.000 claims description 10
238000009835 boiling Methods 0.000 claims description 9
238000006243 chemical reaction Methods 0.000 claims description 9
125000003386 piperidinyl group Chemical group 0.000 claims description 9
238000009833 condensation Methods 0.000 claims description 8
230000005494 condensation Effects 0.000 claims description 8
125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 8
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims description 8
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 8
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 7
229910052757 nitrogen Inorganic materials 0.000 claims description 7
125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
125000002883 imidazolyl group Chemical group 0.000 claims description 6
125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
BSARWJMYHLNELF-UHFFFAOYSA-N n-butyl-n-[3-[4-(2-ethylindolizin-1-yl)sulfonylphenoxy]propyl]butan-1-amine Chemical compound C1=CC(OCCCN(CCCC)CCCC)=CC=C1S(=O)(=O)C1=C2C=CC=CN2C=C1CC BSARWJMYHLNELF-UHFFFAOYSA-N 0.000 claims description 5
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 4
239000002253 acid Substances 0.000 claims description 4
150000001412 amines Chemical class 0.000 claims description 4
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
125000005843 halogen group Chemical group 0.000 claims description 4
125000004076 pyridyl group Chemical group 0.000 claims description 4
239000002246 antineoplastic agent Substances 0.000 claims description 3
229940041181 antineoplastic drug Drugs 0.000 claims description 3
150000007522 mineralic acids Chemical class 0.000 claims description 3
OJPHYJUOPGCSOT-UHFFFAOYSA-N n-butyl-n-[3-[4-(2-propan-2-ylindolizin-1-yl)sulfonylphenoxy]propyl]butan-1-amine Chemical compound C1=CC(OCCCN(CCCC)CCCC)=CC=C1S(=O)(=O)C1=C2C=CC=CN2C=C1C(C)C OJPHYJUOPGCSOT-UHFFFAOYSA-N 0.000 claims description 3
150000007524 organic acids Chemical class 0.000 claims description 3
239000002798 polar solvent Substances 0.000 claims description 3
230000003389 potentiating effect Effects 0.000 claims description 3
150000003254 radicals Chemical class 0.000 claims description 3
230000015572 biosynthetic process Effects 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 5
239000000546 pharmaceutical excipient Substances 0.000 claims 4
125000001424 substituent group Chemical group 0.000 claims 4
125000002774 3,4-dimethoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C(OC([H])([H])[H])=C1OC([H])([H])[H])C([H])([H])* 0.000 claims 3
125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims 3
125000003118 aryl group Chemical group 0.000 claims 3
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 3
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims 1
PPBBSDANFIPZDM-UHFFFAOYSA-N 4-indolizin-1-ylsulfonylphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=C2C=CC=CN2C=C1 PPBBSDANFIPZDM-UHFFFAOYSA-N 0.000 claims 1
125000004429 atom Chemical group 0.000 claims 1
150000003840 hydrochlorides Chemical class 0.000 claims 1
WAPWAAXGLQLAKH-UHFFFAOYSA-N n-[2-(3,4-dimethoxyphenyl)ethyl]-3-[4-(2-ethylindolizin-1-yl)sulfonylphenoxy]-n-methylpropan-1-amine Chemical compound CCC1=CN2C=CC=CC2=C1S(=O)(=O)C(C=C1)=CC=C1OCCCN(C)CCC1=CC=C(OC)C(OC)=C1 WAPWAAXGLQLAKH-UHFFFAOYSA-N 0.000 claims 1
239000012454 non-polar solvent Substances 0.000 claims 1
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract description 7
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract description 3
210000000748 cardiovascular system Anatomy 0.000 abstract 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 96
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 58
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 51
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 42
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 30
239000000243 solution Substances 0.000 description 23
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 20
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 18
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 12
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
239000011575 calcium Substances 0.000 description 11
206010002383 Angina Pectoris Diseases 0.000 description 10
230000000694 effects Effects 0.000 description 10
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 10
239000003921 oil Substances 0.000 description 10
229910000027 potassium carbonate Inorganic materials 0.000 description 10
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
239000002876 beta blocker Substances 0.000 description 9
229910052791 calcium Inorganic materials 0.000 description 9
239000011541 reaction mixture Substances 0.000 description 9
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 8
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
229940097320 beta blocking agent Drugs 0.000 description 8
230000008602 contraction Effects 0.000 description 8
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
239000003795 chemical substances by application Substances 0.000 description 7
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 6
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 6
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 6
229910000288 alkali metal carbonate Inorganic materials 0.000 description 6
150000008041 alkali metal carbonates Chemical class 0.000 description 6
230000001466 anti-adreneric effect Effects 0.000 description 6
239000002585 base Substances 0.000 description 6
230000002526 effect on cardiovascular system Effects 0.000 description 6
229910052700 potassium Inorganic materials 0.000 description 6
239000011591 potassium Substances 0.000 description 6
230000009467 reduction Effects 0.000 description 6
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 5
229910052783 alkali metal Inorganic materials 0.000 description 5
102000012740 beta Adrenergic Receptors Human genes 0.000 description 5
108010079452 beta Adrenergic Receptors Proteins 0.000 description 5
239000012528 membrane Substances 0.000 description 5
WPISNXOKHKTTRN-UHFFFAOYSA-N n-butyl-n-[3-[4-(2-propan-2-ylindolizin-1-yl)sulfanylphenoxy]propyl]butan-1-amine;oxalic acid Chemical compound OC(=O)C(O)=O.C1=CC(OCCCN(CCCC)CCCC)=CC=C1SC1=C2C=CC=CN2C=C1C(C)C WPISNXOKHKTTRN-UHFFFAOYSA-N 0.000 description 5
239000012074 organic phase Substances 0.000 description 5
230000000144 pharmacologic effect Effects 0.000 description 5
239000002244 precipitate Substances 0.000 description 5
239000000047 product Substances 0.000 description 5
238000010992 reflux Methods 0.000 description 5
230000033764 rhythmic process Effects 0.000 description 5
239000000377 silicon dioxide Substances 0.000 description 5
230000001225 therapeutic effect Effects 0.000 description 5
CLQBBAMUAPQHRE-UHFFFAOYSA-N 1-[4-(3-bromopropoxy)phenyl]sulfonyl-2-ethylindolizine Chemical compound CCC1=CN2C=CC=CC2=C1S(=O)(=O)C1=CC=C(OCCCBr)C=C1 CLQBBAMUAPQHRE-UHFFFAOYSA-N 0.000 description 4
XZVULSQFWZMGQV-UHFFFAOYSA-N 4-(2-propan-2-ylindolizin-1-yl)sulfonylphenol Chemical compound CC(C)C1=CN2C=CC=CC2=C1S(=O)(=O)C1=CC=C(O)C=C1 XZVULSQFWZMGQV-UHFFFAOYSA-N 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 4
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 4
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
150000001340 alkali metals Chemical class 0.000 description 4
239000000480 calcium channel blocker Substances 0.000 description 4
238000004440 column chromatography Methods 0.000 description 4
230000001595 contractor effect Effects 0.000 description 4
JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 4
230000002401 inhibitory effect Effects 0.000 description 4
230000028161 membrane depolarization Effects 0.000 description 4
239000003208 petroleum Substances 0.000 description 4
229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
235000017557 sodium bicarbonate Nutrition 0.000 description 4
JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 3
UCTWMZQNUQWSLP-VIFPVBQESA-N (R)-adrenaline Chemical compound CNC[C@H](O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-VIFPVBQESA-N 0.000 description 3
229930182837 (R)-adrenaline Natural products 0.000 description 3
VFYSNYOCGACPOA-UHFFFAOYSA-N 1-(dibutylamino)-3-[4-(2-propan-2-ylindolizin-1-yl)sulfonylphenoxy]propan-2-ol;hydrochloride Chemical compound Cl.C1=CC(OCC(O)CN(CCCC)CCCC)=CC=C1S(=O)(=O)C1=C2C=CC=CN2C=C1C(C)C VFYSNYOCGACPOA-UHFFFAOYSA-N 0.000 description 3
TXRMLXWBMNETGN-UHFFFAOYSA-N 4-(2-propan-2-ylindolizin-1-yl)sulfanylphenol Chemical compound CC(C)C1=CN2C=CC=CC2=C1SC1=CC=C(O)C=C1 TXRMLXWBMNETGN-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 3
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 3
206010020772 Hypertension Diseases 0.000 description 3
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
OSPBPWUJOZPDGM-UHFFFAOYSA-N [4-(2-propan-2-ylindolizin-1-yl)sulfonylphenyl] 4-methylbenzenesulfonate Chemical compound CC(C)C1=CN2C=CC=CC2=C1S(=O)(=O)C(C=C1)=CC=C1OS(=O)(=O)C1=CC=C(C)C=C1 OSPBPWUJOZPDGM-UHFFFAOYSA-N 0.000 description 3
229910000102 alkali metal hydride Inorganic materials 0.000 description 3
150000008046 alkali metal hydrides Chemical class 0.000 description 3
125000005278 alkyl sulfonyloxy group Chemical group 0.000 description 3
210000000709 aorta Anatomy 0.000 description 3
230000036772 blood pressure Effects 0.000 description 3
230000000747 cardiac effect Effects 0.000 description 3
238000004587 chromatography analysis Methods 0.000 description 3
238000001816 cooling Methods 0.000 description 3
239000012153 distilled water Substances 0.000 description 3
239000003814 drug Substances 0.000 description 3
239000003480 eluent Substances 0.000 description 3
229960005139 epinephrine Drugs 0.000 description 3
239000008103 glucose Substances 0.000 description 3
229960001317 isoprenaline Drugs 0.000 description 3
OBSVCIXHMYVRAR-UHFFFAOYSA-N n-butyl-n-[3-[4-(2-propan-2-ylindolizin-1-yl)sulfonylphenoxy]propyl]butan-1-amine;oxalic acid Chemical compound OC(=O)C(O)=O.C1=CC(OCCCN(CCCC)CCCC)=CC=C1S(=O)(=O)C1=C2C=CC=CN2C=C1C(C)C OBSVCIXHMYVRAR-UHFFFAOYSA-N 0.000 description 3
235000006408 oxalic acid Nutrition 0.000 description 3
239000011734 sodium Substances 0.000 description 3
239000012312 sodium hydride Substances 0.000 description 3
229910000104 sodium hydride Inorganic materials 0.000 description 3
125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 description 2
QYBICPAYUFCUKS-UHFFFAOYSA-N 1-[2-[(4-hydroxyphenyl)sulfanylmethyl]pyridin-1-ium-1-yl]-3-methylbutan-2-one;bromide Chemical compound [Br-].CC(C)C(=O)C[N+]1=CC=CC=C1CSC1=CC=C(O)C=C1 QYBICPAYUFCUKS-UHFFFAOYSA-N 0.000 description 2
NNTPEAXKKUPBHQ-UHFFFAOYSA-N 1-bromo-3-methylbutan-2-one Chemical compound CC(C)C(=O)CBr NNTPEAXKKUPBHQ-UHFFFAOYSA-N 0.000 description 2
LFOOXBDWIAJWHW-UHFFFAOYSA-N 2-ethyl-1-[4-(3-piperidin-1-ylpropoxy)phenyl]sulfonylindolizine;hydrochloride Chemical compound Cl.CCC1=CN2C=CC=CC2=C1S(=O)(=O)C(C=C1)=CC=C1OCCCN1CCCCC1 LFOOXBDWIAJWHW-UHFFFAOYSA-N 0.000 description 2
KTVOIVNDOVRIKP-UHFFFAOYSA-N 4-(2-ethylindolizin-1-yl)sulfonylphenol Chemical compound CCC1=CN2C=CC=CC2=C1S(=O)(=O)C1=CC=C(O)C=C1 KTVOIVNDOVRIKP-UHFFFAOYSA-N 0.000 description 2
FMAWAVRGYAKOGW-UHFFFAOYSA-N 4h-indolizin-4-ium;chloride Chemical compound Cl.C1=CC=CN2C=CC=C21 FMAWAVRGYAKOGW-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
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LXEGQSDIQOZITL-UHFFFAOYSA-N [4-(2-phenylindolizin-1-yl)sulfonylphenyl] 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OC1=CC=C(S(=O)(=O)C2=C3C=CC=CN3C=C2C=2C=CC=CC=2)C=C1 LXEGQSDIQOZITL-UHFFFAOYSA-N 0.000 description 1
UQOWVOJXGGTKIV-UHFFFAOYSA-N [4-(2-propylindolizin-1-yl)sulfonylphenyl] 4-methylbenzenesulfonate Chemical compound CCCC1=CN2C=CC=CC2=C1S(=O)(=O)C(C=C1)=CC=C1OS(=O)(=O)C1=CC=C(C)C=C1 UQOWVOJXGGTKIV-UHFFFAOYSA-N 0.000 description 1
UULBGISPCCMKAJ-UHFFFAOYSA-N [4-(2-tert-butylindolizin-1-yl)sulfonylphenyl] 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OC1=CC=C(S(=O)(=O)C2=C3C=CC=CN3C=C2C(C)(C)C)C=C1 UULBGISPCCMKAJ-UHFFFAOYSA-N 0.000 description 1
MAZGPSPJQFPJCX-UHFFFAOYSA-N [4-[3-(dibutylamino)propoxy]phenyl]-(2-ethylindolizin-1-yl)methanone Chemical compound C1=CC(OCCCN(CCCC)CCCC)=CC=C1C(=O)C1=C2C=CC=CN2C=C1CC MAZGPSPJQFPJCX-UHFFFAOYSA-N 0.000 description 1
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239000003513 alkali Substances 0.000 description 1
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239000005557 antagonist Substances 0.000 description 1
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239000008346 aqueous phase Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
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QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
JEHKKBHWRAXMCH-UHFFFAOYSA-M benzenesulfinate Chemical compound [O-]S(=O)C1=CC=CC=C1 JEHKKBHWRAXMCH-UHFFFAOYSA-M 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
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125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
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125000001589 carboacyl group Chemical group 0.000 description 1
239000001569 carbon dioxide Substances 0.000 description 1
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210000000170 cell membrane Anatomy 0.000 description 1
WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 1
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230000005284 excitation Effects 0.000 description 1
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230000001435 haemodynamic effect Effects 0.000 description 1
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208000019622 heart disease Diseases 0.000 description 1
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XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
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LGQXDKCKVGZOQN-UHFFFAOYSA-N indolizin-1-yl(phenyl)methanone Chemical class C1=CN2C=CC=CC2=C1C(=O)C1=CC=CC=C1 LGQXDKCKVGZOQN-UHFFFAOYSA-N 0.000 description 1
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201000004332 intermediate coronary syndrome Diseases 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
230000009916 joint effect Effects 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000008101 lactose Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
238000005259 measurement Methods 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
125000005948 methanesulfonyloxy group Chemical group 0.000 description 1
235000013336 milk Nutrition 0.000 description 1
239000008267 milk Substances 0.000 description 1
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FZFLBSCDHWFWGS-UHFFFAOYSA-N n,n-dibutyl-4-[4-(2-ethylindolizin-1-yl)sulfonylphenoxy]butan-1-amine Chemical compound C1=CC(OCCCCN(CCCC)CCCC)=CC=C1S(=O)(=O)C1=C2C=CC=CN2C=C1CC FZFLBSCDHWFWGS-UHFFFAOYSA-N 0.000 description 1
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NIOVWDWNPNKWSM-UHFFFAOYSA-N n-[(3,4-dimethoxyphenyl)methyl]-3-[4-(2-propan-2-ylindolizin-1-yl)sulfonylphenoxy]propan-1-amine Chemical compound C1=C(OC)C(OC)=CC=C1CNCCCOC1=CC=C(S(=O)(=O)C2=C3C=CC=CN3C=C2C(C)C)C=C1 NIOVWDWNPNKWSM-UHFFFAOYSA-N 0.000 description 1
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DISCNTXZJFHGTJ-UHFFFAOYSA-N n-[2-(3,4-dimethoxyphenyl)ethyl]-n-methyl-3-[4-(2-propan-2-ylindolizin-1-yl)sulfanylphenoxy]propan-1-amine;oxalic acid Chemical compound OC(=O)C(O)=O.C1=C(OC)C(OC)=CC=C1CCN(C)CCCOC(C=C1)=CC=C1SC1=C2C=CC=CN2C=C1C(C)C DISCNTXZJFHGTJ-UHFFFAOYSA-N 0.000 description 1
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DIYJRPZSJBZLBX-UHFFFAOYSA-N n-[3-[4-(2-ethylindolizin-1-yl)sulfonylphenoxy]propyl]-2-methylpropan-2-amine;hydrochloride Chemical compound Cl.CCC1=CN2C=CC=CC2=C1S(=O)(=O)C1=CC=C(OCCCNC(C)(C)C)C=C1 DIYJRPZSJBZLBX-UHFFFAOYSA-N 0.000 description 1
YXZFQUGXVBSNKO-UHFFFAOYSA-N n-[3-[4-(2-ethylindolizin-1-yl)sulfonylphenoxy]propyl]-n-pentylpentan-1-amine;hydrochloride Chemical compound Cl.C1=CC(OCCCN(CCCCC)CCCCC)=CC=C1S(=O)(=O)C1=C2C=CC=CN2C=C1CC YXZFQUGXVBSNKO-UHFFFAOYSA-N 0.000 description 1
DHWCWEDHJPXCEI-UHFFFAOYSA-N n-[3-[4-(2-ethylindolizin-1-yl)sulfonylphenoxy]propyl]butan-1-amine;oxalic acid Chemical compound OC(=O)C(O)=O.C1=CC(OCCCNCCCC)=CC=C1S(=O)(=O)C1=C2C=CC=CN2C=C1CC DHWCWEDHJPXCEI-UHFFFAOYSA-N 0.000 description 1
VZACLYUKKCQZHZ-UHFFFAOYSA-N n-benzyl-3-[4-(2-propan-2-ylindolizin-1-yl)sulfonylphenoxy]propan-1-amine;hydrochloride Chemical compound Cl.CC(C)C1=CN2C=CC=CC2=C1S(=O)(=O)C(C=C1)=CC=C1OCCCNCC1=CC=CC=C1 VZACLYUKKCQZHZ-UHFFFAOYSA-N 0.000 description 1
YHHYKRDPFYEQBI-UHFFFAOYSA-N n-butyl-n-(1-chloropropyl)butan-1-amine Chemical compound CCCCN(C(Cl)CC)CCCC YHHYKRDPFYEQBI-UHFFFAOYSA-N 0.000 description 1
ANLMKUQEPXRMGV-UHFFFAOYSA-N n-butyl-n-(3-chloropropyl)butan-1-amine Chemical compound CCCCN(CCCC)CCCCl ANLMKUQEPXRMGV-UHFFFAOYSA-N 0.000 description 1
QHFXZRABQDVSGU-UHFFFAOYSA-N n-butyl-n-[2-[4-(2-ethylindolizin-1-yl)sulfonylphenoxy]ethyl]butan-1-amine;hydrochloride Chemical compound Cl.C1=CC(OCCN(CCCC)CCCC)=CC=C1S(=O)(=O)C1=C2C=CC=CN2C=C1CC QHFXZRABQDVSGU-UHFFFAOYSA-N 0.000 description 1
FMJMSDFXIAAFSQ-UHFFFAOYSA-N n-butyl-n-[3-[4-(2-ethylindolizin-1-yl)sulfonyl-2,6-dimethylphenoxy]propyl]butan-1-amine;hydrochloride Chemical compound Cl.C1=C(C)C(OCCCN(CCCC)CCCC)=C(C)C=C1S(=O)(=O)C1=C2C=CC=CN2C=C1CC FMJMSDFXIAAFSQ-UHFFFAOYSA-N 0.000 description 1
GOJLFELDGDGKFH-UHFFFAOYSA-N n-butyl-n-[3-[4-(2-ethylindolizin-1-yl)sulfonylphenoxy]propyl]butan-1-amine;hydrochloride Chemical compound Cl.C1=CC(OCCCN(CCCC)CCCC)=CC=C1S(=O)(=O)C1=C2C=CC=CN2C=C1CC GOJLFELDGDGKFH-UHFFFAOYSA-N 0.000 description 1
BMPYCJDRVDHEQG-UHFFFAOYSA-N n-butyl-n-[3-[4-(2-methylindolizin-1-yl)sulfonylphenoxy]propyl]butan-1-amine;oxalic acid Chemical compound OC(=O)C(O)=O.C1=CC(OCCCN(CCCC)CCCC)=CC=C1S(=O)(=O)C1=C2C=CC=CN2C=C1C BMPYCJDRVDHEQG-UHFFFAOYSA-N 0.000 description 1
QDJGWAVLPUZHNP-UHFFFAOYSA-N n-butyl-n-[3-[4-(2-phenylindolizin-1-yl)sulfonylphenoxy]propyl]butan-1-amine;hydrochloride Chemical compound Cl.C1=CC(OCCCN(CCCC)CCCC)=CC=C1S(=O)(=O)C1=C2C=CC=CN2C=C1C1=CC=CC=C1 QDJGWAVLPUZHNP-UHFFFAOYSA-N 0.000 description 1
LGZQUBMIKNEYAS-UHFFFAOYSA-N n-octyl-n-[3-[4-(2-propan-2-ylindolizin-1-yl)sulfonylphenoxy]propyl]octan-1-amine Chemical compound C1=CC(OCCCN(CCCCCCCC)CCCCCCCC)=CC=C1S(=O)(=O)C1=C2C=CC=CN2C=C1C(C)C LGZQUBMIKNEYAS-UHFFFAOYSA-N 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
HYIMSNHJOBLJNT-UHFFFAOYSA-N nifedipine Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1C1=CC=CC=C1[N+]([O-])=O HYIMSNHJOBLJNT-UHFFFAOYSA-N 0.000 description 1
229960001597 nifedipine Drugs 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
210000000056 organ Anatomy 0.000 description 1
BZMMCTGMVBTMHH-UHFFFAOYSA-N oxalic acid;3-[4-(2-propan-2-ylindolizin-1-yl)sulfonylphenoxy]-n,n-dipropylpropan-1-amine Chemical compound OC(=O)C(O)=O.C1=CC(OCCCN(CCC)CCC)=CC=C1S(=O)(=O)C1=C2C=CC=CN2C=C1C(C)C BZMMCTGMVBTMHH-UHFFFAOYSA-N 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
239000012057 packaged powder Substances 0.000 description 1
IPCSVZSSVZVIGE-UHFFFAOYSA-N palmitic acid group Chemical group C(CCCCCCCCCCCCCCC)(=O)O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 1
235000011837 pasties Nutrition 0.000 description 1
230000037361 pathway Effects 0.000 description 1
229960001412 pentobarbital Drugs 0.000 description 1
230000002093 peripheral effect Effects 0.000 description 1
230000035699 permeability Effects 0.000 description 1
229940048346 phenethylamine hydrochloride Drugs 0.000 description 1
125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
ZLMJMSJWJFRBEC-OUBTZVSYSA-N potassium-40 Chemical compound [40K] ZLMJMSJWJFRBEC-OUBTZVSYSA-N 0.000 description 1
239000012264 purified product Substances 0.000 description 1
BBFCIBZLAVOLCF-UHFFFAOYSA-N pyridin-1-ium;bromide Chemical compound Br.C1=CC=NC=C1 BBFCIBZLAVOLCF-UHFFFAOYSA-N 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
239000002464 receptor antagonist Substances 0.000 description 1
229940044551 receptor antagonist Drugs 0.000 description 1
230000011514 reflex Effects 0.000 description 1
230000004044 response Effects 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
210000002460 smooth muscle Anatomy 0.000 description 1
230000016160 smooth muscle contraction Effects 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
229960000278 theophylline Drugs 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
230000036977 tonic contraction Effects 0.000 description 1
229960001722 verapamil Drugs 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- 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
- 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
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- 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
- A61P9/08—Vasodilators for multiple indications
- 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
- 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
- A61P9/12—Antihypertensives

Landscapes

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

SK977-87A 1986-02-14 1987-02-13 Indolizine derivatives, process for their preparation and pharmaceutical or verinary composition containing them SK97787A3 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
FR8602045A FR2594438B1 (fr)	1986-02-14	1986-02-14	Derives d'indolizine, leur procede de preparation ainsi que les compositions en contenant

Publications (2)

Publication Number	Publication Date
SK279557B6 SK279557B6 (sk)	1998-12-02
SK97787A3 true SK97787A3 (en)	1998-12-02

Family

ID=9332147

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK977-87A SK97787A3 (en)	1986-02-14	1987-02-13	Indolizine derivatives, process for their preparation and pharmaceutical or verinary composition containing them

Country Status (33)

Country	Link
US (5)	US4957925A (es)
EP (1)	EP0235111B1 (es)
JP (1)	JP2547004B2 (es)
KR (1)	KR870007931A (es)
AR (1)	AR245127A1 (es)
AT (1)	ATE62485T1 (es)
AU (1)	AU587525B2 (es)
BE (1)	BE1006666A4 (es)
CA (1)	CA1310965C (es)
CZ (1)	CZ281209B6 (es)
DD (1)	DD264436A5 (es)
DE (1)	DE3769174D1 (es)
DK (1)	DK170403B1 (es)
ES (1)	ES2040276T3 (es)
FI (1)	FI84353C (es)
FR (1)	FR2594438B1 (es)
GR (1)	GR3001883T3 (es)
HU (1)	HU196401B (es)
IE (1)	IE59656B1 (es)
IL (1)	IL81358A (es)
MA (1)	MA20878A1 (es)
MY (1)	MY101541A (es)
NO (1)	NO165344C (es)
NZ (1)	NZ219274A (es)
OA (1)	OA08481A (es)
PH (1)	PH24830A (es)
PL (2)	PL152609B1 (es)
PT (1)	PT84277B (es)
SK (1)	SK97787A3 (es)
SU (2)	SU1486064A3 (es)
TN (1)	TNSN87021A1 (es)
YU (2)	YU21287A (es)
ZA (1)	ZA87471B (es)

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1986
- 1986-02-14 FR FR8602045A patent/FR2594438B1/fr not_active Expired - Lifetime
1987
- 1987-01-22 IL IL81358A patent/IL81358A/xx not_active IP Right Cessation
- 1987-01-22 ZA ZA87471A patent/ZA87471B/xx unknown
- 1987-01-26 MY MYPI87000061A patent/MY101541A/en unknown
- 1987-02-06 PH PH34827A patent/PH24830A/en unknown
- 1987-02-10 AT AT87870019T patent/ATE62485T1/de not_active IP Right Cessation
- 1987-02-10 EP EP87870019A patent/EP0235111B1/fr not_active Expired - Lifetime
- 1987-02-10 DE DE8787870019T patent/DE3769174D1/de not_active Expired - Lifetime
- 1987-02-10 ES ES198787870019T patent/ES2040276T3/es not_active Expired - Lifetime
- 1987-02-10 BE BE8700103A patent/BE1006666A4/fr not_active IP Right Cessation
- 1987-02-11 IE IE34587A patent/IE59656B1/en not_active IP Right Cessation
- 1987-02-11 CA CA000529512A patent/CA1310965C/en not_active Expired - Lifetime
- 1987-02-12 PL PL1987264078A patent/PL152609B1/pl unknown
- 1987-02-12 PL PL1987282576A patent/PL153650B1/pl unknown
- 1987-02-12 PT PT84277A patent/PT84277B/pt unknown
- 1987-02-12 AR AR87306719A patent/AR245127A1/es active
- 1987-02-13 NO NO870579A patent/NO165344C/no unknown
- 1987-02-13 CZ CS87977A patent/CZ281209B6/cs not_active IP Right Cessation
- 1987-02-13 HU HU87567A patent/HU196401B/hu unknown
- 1987-02-13 JP JP62032304A patent/JP2547004B2/ja not_active Expired - Lifetime
- 1987-02-13 DK DK074087A patent/DK170403B1/da not_active IP Right Cessation
- 1987-02-13 YU YU00212/87A patent/YU21287A/xx unknown
- 1987-02-13 NZ NZ219274A patent/NZ219274A/xx unknown
- 1987-02-13 MA MA21112A patent/MA20878A1/fr unknown
- 1987-02-13 DD DD87299907A patent/DD264436A5/de not_active IP Right Cessation
- 1987-02-13 OA OA59070A patent/OA08481A/xx unknown
- 1987-02-13 SK SK977-87A patent/SK97787A3/sk unknown
- 1987-02-13 FI FI870629A patent/FI84353C/fi not_active IP Right Cessation
- 1987-02-13 SU SU874202058A patent/SU1486064A3/ru active
- 1987-02-14 KR KR870001238A patent/KR870007931A/ko not_active Withdrawn
- 1987-02-16 AU AU68846/87A patent/AU587525B2/en not_active Expired
- 1987-02-19 TN TNTNSN87021A patent/TNSN87021A1/fr unknown
- 1987-08-07 US US07/082,554 patent/US4957925A/en not_active Expired - Lifetime
- 1987-08-11 SU SU4203068A patent/SU1528321A3/ru active
1988
- 1988-03-08 YU YU00465/88A patent/YU46588A/xx unknown
1989
- 1989-02-06 US US07/306,499 patent/US4994474A/en not_active Expired - Fee Related
- 1989-02-06 US US07/306,498 patent/US5017579A/en not_active Expired - Fee Related
1990
- 1990-03-19 US US07/495,134 patent/US5039700A/en not_active Expired - Fee Related
- 1990-04-19 US US07/511,095 patent/US5147878A/en not_active Expired - Fee Related
1991
- 1991-04-30 GR GR91400559T patent/GR3001883T3/el unknown

Also Published As

Publication number	Publication date
US4957925A (en)	1990-09-18
US5039700A (en)	1991-08-13
PH24830A (en)	1990-10-30
NO165344C (no)	1991-01-30
GR3001883T3 (en)	1992-11-23
EP0235111A1 (fr)	1987-09-02
US4994474A (en)	1991-02-19
FI870629A0 (fi)	1987-02-13
IL81358A (en)	1991-03-10
OA08481A (fr)	1988-07-29
SK279557B6 (sk)	1998-12-02
NO870579D0 (no)	1987-02-13
JPS62192380A (ja)	1987-08-22
DK170403B1 (da)	1995-08-21
SU1528321A3 (ru)	1989-12-07
YU21287A (en)	1988-08-31
PT84277A (en)	1987-03-01
PL264078A1 (en)	1988-07-21
KR870007931A (ko)	1987-09-23
SU1486064A3 (ru)	1989-06-07
CZ97787A3 (en)	1996-07-17
DE3769174D1 (de)	1991-05-16
MY101541A (en)	1991-12-17
NO870579L (no)	1987-08-17
ZA87471B (en)	1988-09-28
AU6884687A (en)	1987-08-20
FI84353C (fi)	1991-11-25
IL81358A0 (en)	1987-08-31
TNSN87021A1 (fr)	1990-01-01
NZ219274A (en)	1989-04-26
ATE62485T1 (de)	1991-04-15
AU587525B2 (en)	1989-08-17
HU196401B (en)	1988-11-28
IE870345L (en)	1987-08-14
NO165344B (no)	1990-10-22
IE59656B1 (en)	1994-03-09
CZ281209B6 (cs)	1996-07-17
BE1006666A4 (fr)	1994-11-16
DD264436A5 (de)	1989-02-01
AR245127A1 (es)	1993-12-30
US5147878A (en)	1992-09-15
PT84277B (pt)	1989-09-14
PL153650B1 (en)	1991-05-31
ES2040276T3 (es)	1993-10-16
HUT43604A (en)	1987-11-30
PL152609B1 (en)	1991-01-31
FI84353B (fi)	1991-08-15
FI870629A7 (fi)	1987-08-15
DK74087A (da)	1987-08-15
FR2594438B1 (fr)	1990-01-26
MA20878A1 (fr)	1987-10-01
US5017579A (en)	1991-05-21
DK74087D0 (da)	1987-02-13
JP2547004B2 (ja)	1996-10-23
FR2594438A1 (fr)	1987-08-21
CA1310965C (en)	1992-12-01
EP0235111B1 (fr)	1991-04-10
YU46588A (en)	1989-08-31

Publication	Publication Date	Title
SK97787A3 (en)	1998-12-02	Indolizine derivatives, process for their preparation and pharmaceutical or verinary composition containing them
KR0165131B1 (ko)	1999-02-18	1,4-벤조티아제핀 유도체
PL168044B1 (pl)	1995-12-30	Sposób wytwarzania pochodnych benzofuranu, benzotiofenu, indolu lub indolizyny PL PL PL
EP1206262A1 (en)	2002-05-22	Npy antagonists: spiroisoquinolinone derivatives
IE51179B1 (en)	1986-10-29	Pyridoxine derivatives,process for preparing them and use in therapeutics
RU2032669C1 (ru)	1995-04-10	Способ получения аминофеноксипроизводных
EP0151006B1 (en)	1991-08-28	Dihydropyridine compounds, their production, pharmaceutical compositions containing them, and methods of producing these compositions
US4704382A (en)	1987-11-03	Phenylpiperazine phosphonates
US5155133A (en)	1992-10-13	Antiarrhythmic compounds and pharmaceutical compositions and methods thereof
PL162318B1 (pl)	1993-09-30	Sposób wytwarzania nowych pochodnych piperydyny PL PL PL
US5444056A (en)	1995-08-22	Aminoalkoxyphenyl derivatives, process for their preparation and compositions containing them
US5576327A (en)	1996-11-19	Treatment of heart rhythym disorders by administration of 3-phenylsulfonyl-3, 7-diazabicyclo[3.3.1]nonane compounds
JPH04217955A (ja)	1992-08-07	置換ベンズインドールイミン誘導体及びその製法
HU199835B (en)	1990-03-28	Process for producing benzoquinolizine derivatives and pharmaceutical compositions comprising such compounds
US4983606A (en)	1991-01-08	Pharmaceutically-active phthalazine compounds
US5565470A (en)	1996-10-15	Cycloaminoalkoxyphenyl derivatives, a process for their preparation as well as the compositions containing them
JPH02250862A (ja)	1990-10-08	アミノアルコキシフェニル誘導体、その製法およびそれを含有する組成物
KR950007179B1 (ko)	1995-07-03	인돌리진 유도체, 그 약제학적 조성물, 그 용도 및 그 제조방법
JPH0123463B2 (es)	1989-05-02
JPS60202884A (ja)	1985-10-14	２‐アリールイミダゾ［４，５‐ｃ］ピリジン類
PL103789B1 (pl)	1979-07-31	Sposob wytwarzania nowych pochodnych chinazoliny
CZ44697A3 (en)	1997-10-15	Carboxamide, sulfonamide and phosphonylamide derivatives, process of their preparation and pharmaceutical composition containing thereof
JPH0517907B2 (es)	1993-03-10
HU209753B (en)	1995-02-28	Process for producing of 3-(4-nitrophenoxy)-propylamine derivatives and pharmaceutical compositions comprising them
JPS6270384A (ja)	1987-03-31	新規なリン酸エステル化合物