LU82983A1 - Nouveaux derives d'indolizine,leur procede de preparation ainsi que leurs applications en therapeutique - Google Patents
Nouveaux derives d'indolizine,leur procede de preparation ainsi que leurs applications en therapeutique Download PDFInfo
- Publication number
- LU82983A1 LU82983A1 LU82983A LU82983A LU82983A1 LU 82983 A1 LU82983 A1 LU 82983A1 LU 82983 A LU82983 A LU 82983A LU 82983 A LU82983 A LU 82983A LU 82983 A1 LU82983 A1 LU 82983A1
- Authority
- LU
- Luxembourg
- Prior art keywords
- indolizine
- propyl
- benzoyl
- oxy
- bromo
- Prior art date
Links
- HOBCFUWDNJPFHB-UHFFFAOYSA-N indolizine Chemical class C1=CC=CN2C=CC=C21 HOBCFUWDNJPFHB-UHFFFAOYSA-N 0.000 title claims description 205
- 238000002360 preparation method Methods 0.000 title claims description 8
- 230000001225 therapeutic effect Effects 0.000 title description 3
- -1 alkyl radical Chemical class 0.000 claims description 310
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 146
- 239000002253 acid Substances 0.000 claims description 111
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 94
- 239000000460 chlorine Substances 0.000 claims description 74
- 150000003839 salts Chemical class 0.000 claims description 36
- 150000002478 indolizines Chemical class 0.000 claims description 34
- 231100000252 nontoxic Toxicity 0.000 claims description 28
- 230000003000 nontoxic effect Effects 0.000 claims description 28
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical group CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 27
- 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
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 26
- 229910052794 bromium Inorganic materials 0.000 claims description 26
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 26
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 23
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 22
- 229910052801 chlorine Inorganic materials 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 22
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 13
- 206010002383 Angina Pectoris Diseases 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- 206010003119 arrhythmia Diseases 0.000 claims description 9
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 9
- 230000008569 process Effects 0.000 claims description 9
- 125000001246 bromo group Chemical group Br* 0.000 claims description 8
- 239000012458 free base Substances 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
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 6
- 239000004480 active ingredient Substances 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 150000002431 hydrogen Chemical class 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
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 6
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical group CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 5
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000000068 chlorophenyl group Chemical group 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 230000001575 pathological effect Effects 0.000 claims description 4
- 208000011580 syndromic disease Diseases 0.000 claims description 4
- 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
- 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
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 239000000010 aprotic solvent Substances 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 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
- 238000005303 weighing Methods 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 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
- 125000004429 atom Chemical group 0.000 claims 1
- 125000000532 dioxanyl group Chemical group 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 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
- 150000003254 radicals Chemical class 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 152
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 72
- 150000001875 compounds Chemical class 0.000 description 48
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 31
- 230000000694 effects Effects 0.000 description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
- 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 15
- 229950007869 butoprozine Drugs 0.000 description 15
- 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 10
- 101150032584 oxy-4 gene Proteins 0.000 description 10
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 description 9
- 230000009467 reduction Effects 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 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 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- UCTWMZQNUQWSLP-VIFPVBQESA-N (R)-adrenaline Chemical compound CNC[C@H](O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-VIFPVBQESA-N 0.000 description 7
- 229930182837 (R)-adrenaline Natural products 0.000 description 7
- 125000001478 1-chloroethyl group Chemical group [H]C([H])([H])C([H])(Cl)* 0.000 description 7
- 241000282472 Canis lupus familiaris Species 0.000 description 7
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- 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
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- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
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- 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
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical class ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 239000002876 beta blocker Substances 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 230000036765 blood level Effects 0.000 description 1
- SMTNXTHHYPIVQU-UHFFFAOYSA-N butanoic acid;oxalic acid Chemical compound CCCC(O)=O.OC(=O)C(O)=O SMTNXTHHYPIVQU-UHFFFAOYSA-N 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
- 239000008119 colloidal silica Substances 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
- 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
- 238000004090 dissolution Methods 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
- ANBZWDBEKOZNHY-UHFFFAOYSA-N ethanol;oxalic acid Chemical compound CCO.OC(=O)C(O)=O ANBZWDBEKOZNHY-UHFFFAOYSA-N 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
- 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
- INDOEUQOOOEPQF-UHFFFAOYSA-N indolizine propan-2-ol Chemical compound CC(C)O.C1=CC=CN2C=CC=C21 INDOEUQOOOEPQF-UHFFFAOYSA-N 0.000 description 1
- 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 208000028867 ischemia Diseases 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- 231100000518 lethal Toxicity 0.000 description 1
- 231100000636 lethal dose Toxicity 0.000 description 1
- 230000001665 lethal effect Effects 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 229910052753 mercury Inorganic materials 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
- 208000031225 myocardial ischemia Diseases 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
- QZYWEVKTBJKUPB-UHFFFAOYSA-N n-butyl-n-chlorobutan-1-amine Chemical compound CCCCN(Cl)CCCC QZYWEVKTBJKUPB-UHFFFAOYSA-N 0.000 description 1
- 230000000050 nutritive effect Effects 0.000 description 1
- NIFHFRBCEUSGEE-UHFFFAOYSA-N oxalic acid Chemical compound OC(=O)C(O)=O.OC(=O)C(O)=O NIFHFRBCEUSGEE-UHFFFAOYSA-N 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 229960001412 pentobarbital Drugs 0.000 description 1
- 229910052698 phosphorus Inorganic materials 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
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000011541 reaction mixture 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
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid 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
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 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
- 238000013519 translation Methods 0.000 description 1
- 208000003663 ventricular fibrillation Diseases 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)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB7942146 | 1979-12-06 | ||
| GB7942146 | 1979-12-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| LU82983A1 true LU82983A1 (fr) | 1981-03-26 |
Family
ID=10509659
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| LU82983A LU82983A1 (fr) | 1979-12-06 | 1980-12-05 | Nouveaux derives d'indolizine,leur procede de preparation ainsi que leurs applications en therapeutique |
Country Status (40)
| Country | Link |
|---|---|
| JP (1) | JPS56103181A (de) |
| AR (4) | AR227036A1 (de) |
| AT (1) | AT376438B (de) |
| AU (1) | AU536320B2 (de) |
| BE (1) | BE886511A (de) |
| BG (2) | BG35598A3 (de) |
| BR (1) | BR8007691A (de) |
| CA (1) | CA1152077A (de) |
| CH (1) | CH651041A5 (de) |
| CS (3) | CS222698B2 (de) |
| DD (1) | DD155069A5 (de) |
| DE (1) | DE3046017C2 (de) |
| DK (1) | DK146977C (de) |
| ES (4) | ES497504A0 (de) |
| FI (1) | FI67846C (de) |
| GR (1) | GR70224B (de) |
| HK (1) | HK65884A (de) |
| HU (1) | HU185019B (de) |
| IE (1) | IE50519B1 (de) |
| IL (1) | IL61385A (de) |
| IN (1) | IN151241B (de) |
| IS (1) | IS1209B6 (de) |
| IT (1) | IT1218424B (de) |
| KE (1) | KE3438A (de) |
| LU (1) | LU82983A1 (de) |
| MA (1) | MA19007A1 (de) |
| NL (1) | NL184683C (de) |
| NO (1) | NO157019C (de) |
| NZ (1) | NZ195754A (de) |
| OA (1) | OA06711A (de) |
| PH (1) | PH17028A (de) |
| PL (3) | PL129365B1 (de) |
| PT (1) | PT72151B (de) |
| RO (3) | RO84707B (de) |
| SE (1) | SE441926B (de) |
| SG (1) | SG33384G (de) |
| SU (3) | SU1058505A3 (de) |
| YU (3) | YU42366B (de) |
| ZA (1) | ZA806831B (de) |
| ZW (1) | ZW28580A1 (de) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SG11201704708QA (en) * | 2014-12-10 | 2017-07-28 | Ono Pharmaceutical Co | Dihydroindolizinone derivative |
Family Cites Families (1)
| 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 IS IS2594A patent/IS1209B6/is unknown
- 1980-11-05 ZA ZA00806831A patent/ZA806831B/xx 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 BG049830A patent/BG35598A3/xx unknown
- 1980-12-01 BG BG062985A patent/BG37379A3/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 PL PL1980228265A patent/PL127999B1/pl unknown
- 1980-12-04 CS CS814016A patent/CS222698B2/cs unknown
- 1980-12-04 PL PL1980231829A patent/PL127865B1/pl unknown
- 1980-12-04 IN IN1344/CAL/80A patent/IN151241B/en unknown
- 1980-12-04 PT PT72151A patent/PT72151B/pt unknown
- 1980-12-04 NZ NZ195754A patent/NZ195754A/en unknown
- 1980-12-04 CS CS808517A patent/CS222692B2/cs unknown
- 1980-12-04 CS CS808517A patent/CS222697B2/cs unknown
- 1980-12-05 DE DE3046017A patent/DE3046017C2/de not_active Expired
- 1980-12-05 LU LU82983A patent/LU82983A1/fr unknown
- 1980-12-05 NO NO803681A patent/NO157019C/no unknown
- 1980-12-05 IT IT26463/80A patent/IT1218424B/it active
- 1980-12-05 FI FI803792A patent/FI67846C/fi not_active IP Right Cessation
- 1980-12-05 SU SU803213301A patent/SU1058505A3/ru active
- 1980-12-05 BE BE0/203053A patent/BE886511A/fr not_active IP Right Cessation
- 1980-12-05 ES ES497504A patent/ES497504A0/es active Granted
- 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 DK DK521980A patent/DK146977C/da not_active IP Right Cessation
- 1980-12-05 AT AT0596780A patent/AT376438B/de not_active IP Right Cessation
- 1980-12-05 RO RO108949A patent/RO85271B/ro unknown
- 1980-12-05 RO RO102781A patent/RO81452B/ro unknown
- 1980-12-05 JP JP17252180A patent/JPS56103181A/ja active Granted
- 1980-12-06 DD DD80225817A patent/DD155069A5/de unknown
- 1980-12-06 AR AR283495A patent/AR227036A1/es active
- 1980-12-06 OA OA57269A patent/OA06711A/xx unknown
-
1981
- 1981-12-16 ES ES508051A patent/ES508051A0/es active Granted
- 1981-12-16 ES ES508053A patent/ES508053A0/es active Granted
- 1981-12-16 ES ES508052A patent/ES508052A0/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 YU443/83A patent/YU42840B/xx unknown
- 1983-02-24 YU YU444/83A patent/YU42127B/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
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