CH651041A5 - Indolizine derivatives, process for their preparation and their therapeutic applications - Google Patents

Indolizine derivatives, process for their preparation and their therapeutic applications Download PDF

Info

Publication number: CH651041A5
Authority: CH; Switzerland
Prior art keywords: indolizine; propyl; oxy; benzoyl; bromo
Prior art date: 1979-12-06

Application number

CH8289/80A

Other languages

English (en)

French (fr)

Inventor

Gilbert Rosseels

Henri Inion

Original Assignee

Labaz Sanofi Nv

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.)

1979-12-06

Filing date

1980-11-07

Publication date

1985-08-30

1980-11-07 Application filed by Labaz Sanofi Nv filed Critical Labaz Sanofi Nv

1985-08-30 Publication of CH651041A5 publication Critical patent/CH651041A5/fr

Links

238000000034 method Methods 0.000 title claims description 17
230000008569 process Effects 0.000 title claims description 7
238000002360 preparation method Methods 0.000 title claims description 6
125000003406 indolizinyl group Chemical class C=1(C=CN2C=CC=CC12)* 0.000 title description 2
230000001225 therapeutic effect Effects 0.000 title description 2
HOBCFUWDNJPFHB-UHFFFAOYSA-N indolizine Chemical compound C1=CC=CN2C=CC=C21 HOBCFUWDNJPFHB-UHFFFAOYSA-N 0.000 claims description 189
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 165
-1 alkyl radical Chemical class 0.000 claims description 155
239000002253 acid Substances 0.000 claims description 137
239000000460 chlorine Substances 0.000 claims description 103
101150032584 oxy-4 gene Proteins 0.000 claims description 89
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 41
150000003839 salts Chemical class 0.000 claims description 36
150000002478 indolizines Chemical class 0.000 claims description 31
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical group CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 30
231100000252 nontoxic Toxicity 0.000 claims description 28
230000003000 nontoxic effect Effects 0.000 claims description 28
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 27
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 26
UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 26
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 24
229910052794 bromium Inorganic materials 0.000 claims description 24
229910052801 chlorine Inorganic materials 0.000 claims description 22
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 15
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 13
239000000203 mixture Substances 0.000 claims description 13
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 12
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 12
125000001309 chloro group Chemical group Cl* 0.000 claims description 10
239000001257 hydrogen Substances 0.000 claims description 10
229910052739 hydrogen Inorganic materials 0.000 claims description 10
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 8
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 7
229910052783 alkali metal Inorganic materials 0.000 claims description 7
239000011630 iodine Chemical group 0.000 claims description 7
229910052740 iodine Inorganic materials 0.000 claims description 7
239000002904 solvent Substances 0.000 claims description 7
239000004480 active ingredient Substances 0.000 claims description 6
125000005843 halogen group Chemical group 0.000 claims description 6
150000007522 mineralic acids Chemical class 0.000 claims description 6
150000007524 organic acids Chemical class 0.000 claims description 6
125000004432 carbon atom Chemical group C* 0.000 claims description 5
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 5
239000000546 pharmaceutical excipient Substances 0.000 claims description 5
239000003937 drug carrier Substances 0.000 claims description 4
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical group [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims description 3
125000003545 alkoxy group Chemical group 0.000 claims description 3
125000000217 alkyl group Chemical group 0.000 claims description 3
125000001246 bromo group Chemical group Br* 0.000 claims description 3
239000011737 fluorine Substances 0.000 claims description 3
229910052731 fluorine Inorganic materials 0.000 claims description 3
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
125000001424 substituent group Chemical group 0.000 claims description 3
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 2
125000003282 alkyl amino group Chemical group 0.000 claims description 2
125000003118 aryl group Chemical group 0.000 claims description 2
239000001632 sodium acetate Substances 0.000 claims description 2
235000017281 sodium acetate Nutrition 0.000 claims description 2
125000003944 tolyl group Chemical group 0.000 claims description 2
150000002431 hydrogen Chemical class 0.000 claims 3
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 claims 1
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims 1
229910052736 halogen Inorganic materials 0.000 claims 1
239000012442 inert solvent Substances 0.000 claims 1
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims 1
125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 claims 1
229910052708 sodium Inorganic materials 0.000 claims 1
239000011734 sodium Substances 0.000 claims 1
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 176
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 116
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 103
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 72
150000001875 compounds Chemical class 0.000 description 57
WPWHSFAFEBZWBB-UHFFFAOYSA-N 1-butyl radical Chemical compound [CH2]CCC WPWHSFAFEBZWBB-UHFFFAOYSA-N 0.000 description 42
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 32
HELWPKXYCGJQKR-UHFFFAOYSA-N CCCC(O)=O.C1=CC=CN2C=CC=C21 Chemical compound CCCC(O)=O.C1=CC=CN2C=CC=C21 HELWPKXYCGJQKR-UHFFFAOYSA-N 0.000 description 27
230000000694 effects Effects 0.000 description 27
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
NRTGWAAGLRTUJZ-UHFFFAOYSA-N [4-[3-(dibutylamino)propoxy]phenyl]-(2-ethylindolizin-3-yl)methanone Chemical compound C1=CC(OCCCN(CCCC)CCCC)=CC=C1C(=O)C1=C(CC)C=C2N1C=CC=C2 NRTGWAAGLRTUJZ-UHFFFAOYSA-N 0.000 description 18
OCBFFGCSTGGPSQ-UHFFFAOYSA-N [CH2]CC Chemical compound [CH2]CC OCBFFGCSTGGPSQ-UHFFFAOYSA-N 0.000 description 18
229950007869 butoprozine Drugs 0.000 description 18
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 12
239000012458 free base Substances 0.000 description 9
230000009467 reduction Effects 0.000 description 9
239000000243 solution Substances 0.000 description 9
UCTWMZQNUQWSLP-VIFPVBQESA-N (R)-adrenaline Chemical group CNC[C@H](O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-VIFPVBQESA-N 0.000 description 8
229930182837 (R)-adrenaline Natural products 0.000 description 8
206010002383 Angina Pectoris Diseases 0.000 description 8
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
229960005139 epinephrine Drugs 0.000 description 8
241000282472 Canis lupus familiaris Species 0.000 description 7
239000004615 ingredient Substances 0.000 description 7
238000012360 testing method Methods 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 description 6
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 6
ITPDYQOUSLNIHG-UHFFFAOYSA-N Amiodarone hydrochloride Chemical compound [Cl-].CCCCC=1OC2=CC=CC=C2C=1C(=O)C1=CC(I)=C(OCC[NH+](CC)CC)C(I)=C1 ITPDYQOUSLNIHG-UHFFFAOYSA-N 0.000 description 6
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 6
SIGHKWWTZOUJBK-UHFFFAOYSA-N C(C(=O)O)(=O)O.C=1C=CN2C=CC=CC12 Chemical compound C(C(=O)O)(=O)O.C=1C=CN2C=CC=CC12 SIGHKWWTZOUJBK-UHFFFAOYSA-N 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
229960005260 amiodarone Drugs 0.000 description 6
206010003119 arrhythmia Diseases 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 6
210000004165 myocardium Anatomy 0.000 description 6
230000036284 oxygen consumption Effects 0.000 description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
239000000047 product Substances 0.000 description 6
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical group CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 5
125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 5
206010047281 Ventricular arrhythmia Diseases 0.000 description 5
230000036772 blood pressure Effects 0.000 description 5
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
230000000144 pharmacologic effect Effects 0.000 description 5
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
241001465754 Metazoa Species 0.000 description 4
JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 4
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
238000001816 cooling Methods 0.000 description 4
230000002526 effect on cardiovascular system Effects 0.000 description 4
125000004435 hydrogen atom Chemical class [H]* 0.000 description 4
239000001301 oxygen Substances 0.000 description 4
229910052760 oxygen Inorganic materials 0.000 description 4
125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 4
239000012429 reaction media Substances 0.000 description 4
238000003756 stirring Methods 0.000 description 4
231100000419 toxicity Toxicity 0.000 description 4
230000001988 toxicity Effects 0.000 description 4
125000001478 1-chloroethyl group Chemical group [H]C([H])([H])C([H])(Cl)* 0.000 description 3
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
241000699670 Mus sp. Species 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
230000001466 anti-adreneric effect Effects 0.000 description 3
230000003257 anti-anginal effect Effects 0.000 description 3
239000002585 base Substances 0.000 description 3
239000002775 capsule Substances 0.000 description 3
230000000747 cardiac effect Effects 0.000 description 3
HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 3
IZEKFCXSFNUWAM-UHFFFAOYSA-N dipyridamole Chemical compound C=12N=C(N(CCO)CCO)N=C(N3CCCCC3)C2=NC(N(CCO)CCO)=NC=1N1CCCCC1 IZEKFCXSFNUWAM-UHFFFAOYSA-N 0.000 description 3
229960002768 dipyridamole Drugs 0.000 description 3
INDOEUQOOOEPQF-UHFFFAOYSA-N indolizine propan-2-ol Chemical compound CC(C)O.C1=CC=CN2C=CC=C21 INDOEUQOOOEPQF-UHFFFAOYSA-N 0.000 description 3
235000011837 pasties Nutrition 0.000 description 3
229910000027 potassium carbonate Inorganic materials 0.000 description 3
238000010992 reflux Methods 0.000 description 3
HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 2
IJFXRHURBJZNAO-UHFFFAOYSA-N 3-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=CC(O)=C1 IJFXRHURBJZNAO-UHFFFAOYSA-N 0.000 description 2
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-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
UMCPZXFKYQJKFQ-UHFFFAOYSA-N CCCCCCC.C=1C=CN2C=CC=CC12 Chemical compound CCCCCCC.C=1C=CN2C=CC=CC12 UMCPZXFKYQJKFQ-UHFFFAOYSA-N 0.000 description 2
206010020772 Hypertension Diseases 0.000 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
241000700159 Rattus Species 0.000 description 2
229920002472 Starch Polymers 0.000 description 2
230000001133 acceleration Effects 0.000 description 2
231100000215 acute (single dose) toxicity testing Toxicity 0.000 description 2
238000011047 acute toxicity test Methods 0.000 description 2
230000006793 arrhythmia Effects 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 2
235000019445 benzyl alcohol Nutrition 0.000 description 2
230000036765 blood level Effects 0.000 description 2
208000006218 bradycardia Diseases 0.000 description 2
230000036471 bradycardia Effects 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
239000008119 colloidal silica Substances 0.000 description 2
230000007812 deficiency Effects 0.000 description 2
238000004090 dissolution Methods 0.000 description 2
239000003480 eluent Substances 0.000 description 2
238000010828 elution Methods 0.000 description 2
229910052500 inorganic mineral Inorganic materials 0.000 description 2
238000001990 intravenous administration Methods 0.000 description 2
231100001231 less toxic Toxicity 0.000 description 2
231100000636 lethal dose Toxicity 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
239000011707 mineral Substances 0.000 description 2
230000002107 myocardial effect Effects 0.000 description 2
208000031225 myocardial ischemia Diseases 0.000 description 2
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238000007911 parenteral administration Methods 0.000 description 2
230000001575 pathological effect Effects 0.000 description 2
WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
239000011591 potassium Substances 0.000 description 2
230000002035 prolonged effect Effects 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
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159000000000 sodium salts Chemical class 0.000 description 2
238000001228 spectrum Methods 0.000 description 2
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239000000725 suspension Substances 0.000 description 2
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208000011580 syndromic disease Diseases 0.000 description 2
238000002560 therapeutic procedure Methods 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
VEFLKXRACNJHOV-UHFFFAOYSA-N 1,3-dibromopropane Chemical compound BrCCCBr VEFLKXRACNJHOV-UHFFFAOYSA-N 0.000 description 1
BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical group CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 1
125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
CPKISUMKCULUNR-UHFFFAOYSA-N 2-methoxy-2-oxoacetic acid Chemical compound COC(=O)C(O)=O CPKISUMKCULUNR-UHFFFAOYSA-N 0.000 description 1
125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 1
SOQWSEWRMYFXRL-UHFFFAOYSA-N 4-(4-methylphenyl)sulfonyloxybenzoic acid Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OC1=CC=C(C(O)=O)C=C1 SOQWSEWRMYFXRL-UHFFFAOYSA-N 0.000 description 1
VDQAETCUODSQQV-UHFFFAOYSA-N 5,6-dichloro-5-methoxycyclohexa-1,3-diene Chemical compound COC1(Cl)C=CC=CC1Cl VDQAETCUODSQQV-UHFFFAOYSA-N 0.000 description 1
FWEOQOXTVHGIFQ-UHFFFAOYSA-N 8-anilinonaphthalene-1-sulfonic acid Chemical compound C=12C(S(=O)(=O)O)=CC=CC2=CC=CC=1NC1=CC=CC=C1 FWEOQOXTVHGIFQ-UHFFFAOYSA-N 0.000 description 1
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DZCKBBOUTRRMKD-UHFFFAOYSA-N CO.C=1C=CN2C=CC=CC12 Chemical compound CO.C=1C=CN2C=CC=CC12 DZCKBBOUTRRMKD-UHFFFAOYSA-N 0.000 description 1
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VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
241000282412 Homo Species 0.000 description 1
RKUNBYITZUJHSG-UHFFFAOYSA-N Hyosciamin-hydrochlorid Natural products CN1C(C2)CCC1CC2OC(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-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
241000699666 Mus <mouse, genus> Species 0.000 description 1
239000005708 Sodium hypochlorite Substances 0.000 description 1
208000001871 Tachycardia Diseases 0.000 description 1
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WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
239000012346 acetyl chloride Substances 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
230000000397 acetylating effect Effects 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
230000009471 action Effects 0.000 description 1
230000001154 acute effect Effects 0.000 description 1
150000001263 acyl chlorides Chemical class 0.000 description 1
239000000783 alginic acid Substances 0.000 description 1
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150000004781 alginic acids Chemical class 0.000 description 1
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230000003042 antagnostic effect Effects 0.000 description 1
230000003288 anthiarrhythmic effect Effects 0.000 description 1
239000000010 aprotic solvent Substances 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
230000001746 atrial effect Effects 0.000 description 1
RKUNBYITZUJHSG-SPUOUPEWSA-N atropine Chemical compound O([C@H]1C[C@H]2CC[C@@H](C1)N2C)C(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-SPUOUPEWSA-N 0.000 description 1
229960000396 atropine Drugs 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
230000008901 benefit Effects 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
239000008280 blood Substances 0.000 description 1
210000004369 blood Anatomy 0.000 description 1
231100000259 cardiotoxicity Toxicity 0.000 description 1
210000000748 cardiovascular system Anatomy 0.000 description 1
230000007681 cardiovascular toxicity Effects 0.000 description 1
230000001684 chronic effect Effects 0.000 description 1
231100000132 chronic toxicity testing Toxicity 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
230000001335 demethylating effect Effects 0.000 description 1
230000003001 depressive effect Effects 0.000 description 1
238000011161 development Methods 0.000 description 1
125000003963 dichloro group Chemical group Cl* 0.000 description 1
125000000532 dioxanyl group Chemical group 0.000 description 1
WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
208000035475 disorder Diseases 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
239000008298 dragée Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003814 drug Substances 0.000 description 1
230000001747 exhibiting effect Effects 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
235000003599 food sweetener Nutrition 0.000 description 1
230000026030 halogenation Effects 0.000 description 1
238000005658 halogenation reaction Methods 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
229940071870 hydroiodic acid Drugs 0.000 description 1
208000013403 hyperactivity Diseases 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
238000010253 intravenous injection Methods 0.000 description 1
239000008101 lactose Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
230000002503 metabolic effect Effects 0.000 description 1
238000006198 methoxylation reaction Methods 0.000 description 1
230000011987 methylation Effects 0.000 description 1
238000007069 methylation reaction Methods 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
230000000050 nutritive effect Effects 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
229960001412 pentobarbital Drugs 0.000 description 1
239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 1
235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
229920000053 polysorbate 80 Polymers 0.000 description 1
229940068968 polysorbate 80 Drugs 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
239000000843 powder Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000001294 propane Substances 0.000 description 1
238000011160 research Methods 0.000 description 1
230000001020 rhythmical effect Effects 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
230000035943 smell Effects 0.000 description 1
SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000000126 substance 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
230000006794 tachycardia Effects 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
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
230000001052 transient effect Effects 0.000 description 1
238000013519 translation Methods 0.000 description 1
208000003663 ventricular fibrillation Diseases 0.000 description 1
238000005303 weighing Methods 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
- 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

Landscapes

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

CH8289/80A 1979-12-06 1980-11-07 Indolizine derivatives, process for their preparation and their therapeutic applications CH651041A5 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB7942146		1979-12-06

Publications (1)

Publication Number	Publication Date
CH651041A5 true CH651041A5 (en)	1985-08-30

Family

ID=10509659

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH8289/80A CH651041A5 (en)	1979-12-06	1980-11-07	Indolizine derivatives, process for their preparation and their therapeutic applications

Country Status (40)

Country	Link
JP (1)	JPS56103181A (pl)
AR (4)	AR227036A1 (pl)
AT (1)	AT376438B (pl)
AU (1)	AU536320B2 (pl)
BE (1)	BE886511A (pl)
BG (2)	BG37379A3 (pl)
BR (1)	BR8007691A (pl)
CA (1)	CA1152077A (pl)
CH (1)	CH651041A5 (pl)
CS (3)	CS222698B2 (pl)
DD (1)	DD155069A5 (pl)
DE (1)	DE3046017C2 (pl)
DK (1)	DK146977C (pl)
ES (4)	ES8205798A1 (pl)
FI (1)	FI67846C (pl)
GR (1)	GR70224B (pl)
HK (1)	HK65884A (pl)
HU (1)	HU185019B (pl)
IE (1)	IE50519B1 (pl)
IL (1)	IL61385A (pl)
IN (1)	IN151241B (pl)
IS (1)	IS1209B6 (pl)
IT (1)	IT1218424B (pl)
KE (1)	KE3438A (pl)
LU (1)	LU82983A1 (pl)
MA (1)	MA19007A1 (pl)
NL (1)	NL184683C (pl)
NO (1)	NO157019C (pl)
NZ (1)	NZ195754A (pl)
OA (1)	OA06711A (pl)
PH (1)	PH17028A (pl)
PL (3)	PL129365B1 (pl)
PT (1)	PT72151B (pl)
RO (3)	RO81452B (pl)
SE (1)	SE441926B (pl)
SG (1)	SG33384G (pl)
SU (3)	SU1058505A3 (pl)
YU (3)	YU42366B (pl)
ZA (1)	ZA806831B (pl)
ZW (1)	ZW28580A1 (pl)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AU2015362422B2 (en) *	2014-12-10	2019-11-14	Ono Pharmaceutical Co., Ltd.	Dihydroindolizinone derivative

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1518443A (en)	1976-02-19	1978-07-19	Labaz	Indolizine derivatives and process for preparing the same

1980
- 1980-10-31 IL IL61385A patent/IL61385A/xx unknown
- 1980-11-04 GR GR63275A patent/GR70224B/el unknown
- 1980-11-05 ZA ZA00806831A patent/ZA806831B/xx unknown
- 1980-11-05 IS IS2594A patent/IS1209B6/is unknown
- 1980-11-07 CH CH8289/80A patent/CH651041A5/fr not_active IP Right Cessation
- 1980-11-12 AU AU64292/80A patent/AU536320B2/en not_active Ceased
- 1980-11-13 PH PH24853A patent/PH17028A/en unknown
- 1980-11-19 NL NLAANVRAGE8006310,A patent/NL184683C/xx not_active IP Right Cessation
- 1980-11-25 BR BR8007691A patent/BR8007691A/pt unknown
- 1980-11-26 ZW ZW285/80A patent/ZW28580A1/xx unknown
- 1980-12-01 BG BG062985A patent/BG37379A3/xx unknown
- 1980-12-01 BG BG049830A patent/BG35598A3/xx unknown
- 1980-12-01 CA CA000365859A patent/CA1152077A/en not_active Expired
- 1980-12-02 SE SE8008444A patent/SE441926B/sv not_active IP Right Cessation
- 1980-12-02 YU YU3041/80A patent/YU42366B/xx unknown
- 1980-12-03 MA MA19209A patent/MA19007A1/fr unknown
- 1980-12-03 IE IE2520/80A patent/IE50519B1/en unknown
- 1980-12-04 PL PL1980231828A patent/PL129365B1/pl unknown
- 1980-12-04 CS CS814016A patent/CS222698B2/cs unknown
- 1980-12-04 PT PT72151A patent/PT72151B/pt unknown
- 1980-12-04 IN IN1344/CAL/80A patent/IN151241B/en unknown
- 1980-12-04 CS CS808517A patent/CS222697B2/cs unknown
- 1980-12-04 NZ NZ195754A patent/NZ195754A/en unknown
- 1980-12-04 CS CS808517A patent/CS222692B2/cs unknown
- 1980-12-04 PL PL1980231829A patent/PL127865B1/pl unknown
- 1980-12-04 PL PL1980228265A patent/PL127999B1/pl unknown
- 1980-12-05 SU SU803213301A patent/SU1058505A3/ru active
- 1980-12-05 IT IT26463/80A patent/IT1218424B/it active
- 1980-12-05 RO RO102781A patent/RO81452B/ro unknown
- 1980-12-05 RO RO108948A patent/RO84707B/ro unknown
- 1980-12-05 HU HU802915A patent/HU185019B/hu not_active IP Right Cessation
- 1980-12-05 RO RO108949A patent/RO85271B/ro unknown
- 1980-12-05 LU LU82983A patent/LU82983A1/fr unknown
- 1980-12-05 DK DK521980A patent/DK146977C/da not_active IP Right Cessation
- 1980-12-05 ES ES497504A patent/ES8205798A1/es not_active Expired
- 1980-12-05 NO NO803681A patent/NO157019C/no unknown
- 1980-12-05 DE DE3046017A patent/DE3046017C2/de not_active Expired
- 1980-12-05 AT AT0596780A patent/AT376438B/de not_active IP Right Cessation
- 1980-12-05 FI FI803792A patent/FI67846C/fi not_active IP Right Cessation
- 1980-12-05 JP JP17252180A patent/JPS56103181A/ja active Granted
- 1980-12-05 BE BE0/203053A patent/BE886511A/fr not_active IP Right Cessation
- 1980-12-06 DD DD80225817A patent/DD155069A5/de unknown
- 1980-12-06 OA OA57269A patent/OA06711A/xx unknown
- 1980-12-06 AR AR283495A patent/AR227036A1/es active
1981
- 1981-12-16 ES ES508052A patent/ES508052A0/es active Granted
- 1981-12-16 ES ES508051A patent/ES508051A0/es active Granted
- 1981-12-16 ES ES508053A patent/ES508053A0/es active Granted
- 1981-12-22 SU SU813367150A patent/SU1109051A3/ru active
1982
- 1982-02-24 AR AR288533A patent/AR227093A1/es active
- 1982-02-24 AR AR288535A patent/AR229692A1/es active
- 1982-02-24 AR AR227094A patent/AR227094A1/es active
1983
- 1983-02-24 YU YU444/83A patent/YU42127B/xx unknown
- 1983-02-24 YU YU443/83A patent/YU42840B/xx unknown
1984
- 1984-04-25 SG SG33384A patent/SG33384G/en unknown
- 1984-08-13 KE KE3438A patent/KE3438A/xx unknown
- 1984-08-23 HK HK658/84A patent/HK65884A/xx unknown
- 1984-10-12 SU SU843801012A patent/SU1287751A3/ru active

Also Published As

Publication number	Publication date
ES8300109A1 (es)	1982-10-01
CS222698B2 (en)	1983-07-29
PT72151B (en)	1981-10-28
SE8008444L (sv)	1981-06-07
AR227094A1 (es)	1982-09-15
CS222697B2 (en)	1983-07-29
DK146977C (da)	1984-08-13
IE802520L (en)	1981-06-06
AR229692A1 (es)	1983-10-31
YU304180A (en)	1983-10-31
IS2594A7 (is)	1981-06-07
PL127865B1 (en)	1983-12-31
ES497504A0 (es)	1982-06-16
PL231828A1 (pl)	1982-03-15
ZW28580A1 (en)	1981-08-26
FI803792L (fi)	1981-06-07
AU536320B2 (en)	1984-05-03
ATA596780A (de)	1984-04-15
NZ195754A (en)	1984-03-16
HU185019B (en)	1984-11-28
JPS56103181A (en)	1981-08-18
GR70224B (pl)	1982-08-31
ES8300108A1 (es)	1982-10-01
ES8300110A1 (es)	1982-10-01
RO85271A (ro)	1984-09-29
PL231829A1 (pl)	1982-03-15
BG35598A3 (en)	1984-05-15
YU44483A (en)	1983-10-31
AR227093A1 (es)	1982-09-15
IL61385A0 (en)	1980-12-31
BR8007691A (pt)	1981-06-09
AR227036A1 (es)	1982-09-15
RO81452A (ro)	1983-04-29
IT1218424B (it)	1990-04-19
PH17028A (en)	1984-05-17
DK521980A (da)	1981-06-07
ES508051A0 (es)	1982-10-01
RO84707B (ro)	1984-09-30
DE3046017C2 (de)	1986-09-25
IS1209B6 (is)	1986-03-24
SU1109051A3 (ru)	1984-08-15
ES8205798A1 (es)	1982-06-16
IE50519B1 (en)	1986-04-30
RO81452B (ro)	1983-04-30
DK146977B (da)	1984-03-05
ES508053A0 (es)	1982-10-01
IT8026463A0 (it)	1980-12-05
BE886511A (fr)	1981-06-05
FI67846B (fi)	1985-02-28
SG33384G (en)	1985-02-08
AU6429280A (en)	1981-06-11
NL8006310A (nl)	1981-07-01
LU82983A1 (fr)	1981-03-26
IL61385A (en)	1984-11-30
SU1058505A3 (ru)	1983-11-30
BG37379A3 (en)	1985-05-15
JPS6325591B2 (pl)	1988-05-26
YU42840B (en)	1988-12-31
RO84707A (ro)	1984-07-17
NO157019C (no)	1988-01-06
OA06711A (fr)	1982-06-30
KE3438A (en)	1984-08-24
NL184683B (nl)	1989-05-01
IN151241B (pl)	1983-03-12
AT376438B (de)	1984-11-26
NL184683C (nl)	1989-10-02
DD155069A5 (de)	1982-05-12
PL228265A1 (pl)	1981-11-13
DE3046017A1 (de)	1981-09-03
RO85271B (ro)	1984-10-30
PL127999B1 (en)	1983-12-31
FI67846C (fi)	1985-06-10
CS222692B2 (en)	1983-07-29
MA19007A1 (fr)	1981-07-01
PT72151A (en)	1981-01-01
ZA806831B (en)	1981-10-28
SU1287751A3 (ru)	1987-01-30
YU42366B (en)	1988-08-31
PL129365B1 (en)	1984-05-31
HK65884A (en)	1984-08-31
NO803681L (no)	1981-06-09
ES508052A0 (es)	1982-10-01
CA1152077A (en)	1983-08-16
NO157019B (no)	1987-09-28
YU42127B (en)	1988-04-30
YU44383A (en)	1983-10-31
SE441926B (sv)	1985-11-18

Publication	Publication Date	Title
US4256758A (en)	1981-03-17	4-Substituted-3-hydroxy-3-pyrroline-2,5-dione inhibitors of glycolic acid oxidase
EP0040591B1 (fr)	1983-06-22	Dérivés de pyridoxine, leur procédé de préparation ainsi que leur utilisation en thérapeutique
EP0202164B1 (fr)	1989-02-08	Dérivés de (benzoyl-4 pipéridino)-2 phenyl-1 alcanols, leur préparation et leur application en thérapeutique
JP2637737B2 (ja)	1997-08-06	新規な薬剤
CH653025A5 (fr)	1985-12-13	Oxazolidine-2,4-diones substituees en position 5 douees d'activite hypoglycemique.
CA2415847C (fr)	2011-09-27	Aminoalkylbenzoyl-benzofuranes ou benzothiophenes, leur procede de preparation et les compositions les contenant
CH640837A5 (fr)	1984-01-31	Derives de l'imidazole.
CH617697A5 (pl)	1980-06-13
EP0037778A1 (fr)	1981-10-14	Benzodioxanne 1,4 méthoxy-2 propanolamines, leur préparation et leur application en tant que médicaments
EP0031753B1 (fr)	1984-09-19	Nouveaux dérivés de la (pipéridyl-4)-2 (quinolyl-4)-1 éthanone, produits intermédiaires et procédés pour leur préparation, et leur utilisation comme médicaments
FR2813308A1 (fr)	2002-03-01	Aminoalkoxybenzoyl-benzofurannes ou benzothiophenes, leur procede de preparation ainsi que les compositions les contenant
FR2480284A1 (fr)	1981-10-16	Amines antihypertensives, leur procede de preparation et compositions antihypertensives en contenant.
CH647772A5 (fr)	1985-02-15	Derives de la 5h-furanone-2 et de la 3h-dihydro-furanone-2, leurs procedes de preparation, et medicament les contenant.
US4520026A (en)	1985-05-28	Indolizine derivatives and use as cardiovascular agents
US3998835A (en)	1976-12-21	1-Substituted amino-3-thieno-[3,2-c]pyridinyloxy-2-propanols
CH651041A5 (en)	1985-08-30	Indolizine derivatives, process for their preparation and their therapeutic applications
FR2495470A1 (fr)	1982-06-11	Nouveaux medicaments a base de derives de (quinolyl-4)-1 (piperidyl-4)-2 ethanol ou (quinolyl-4)-1 (piperidyl-4)-3 propanol
FR2646349A1 (fr)	1990-11-02	Derives du 4-phenylmethyl lh-indole, procede et intermediaires de preparation, application a titre de medicaments et compositions les renfermant
US3793334A (en)	1974-02-19	4-benzoyl-4-hydroxy-3-phenyl-1-substituted piperidines
US4378362A (en)	1983-03-29	Indolizine derivatives and process for preparing the same
FR2495616A1 (fr)	1982-06-11	Nouveaux derives d'indolizine, leur procede de preparation ainsi que leurs applications en therapeutique
US4129658A (en)	1978-12-12	4-Styryl-hexahydro-4-indolinols
FR2560873A1 (fr)	1985-09-13	Medicaments a base de derives de la piperidine, nouveaux derives de la piperidine et leurs procedes de preparation
EP0103500B1 (fr)	1988-01-13	Dérivés de phénéthyl-1alpha-phényl-pipéridine-3-propanenitrile, leur préparation et leur application en thérapeutique
FR2692894A1 (fr)	1993-12-31	Aryl-1-(o-alcoxy-phényl-4-pipérazinyl-1)-2, 3- ou 4-alcanols, leur procédé de préparation et leur utilisation pour la préparation de médicaments.

Legal Events

Date	Code	Title	Description
1990-07-31	PL	Patent ceased
2024-10-31	PL	Patent ceased