LU81960A1 - Nouveaux derives de la thienopyridine,leur preparation et les medicaments qui les contiennent - Google Patents

Nouveaux derives de la thienopyridine,leur preparation et les medicaments qui les contiennent Download PDF

Info

Publication number: LU81960A1
Authority: LU; Luxembourg
Prior art keywords: general formula; tetrahydro; pyridine; thieno; isoquinolyl
Prior art date: 1978-12-07

Application number

LU81960A

Other languages

English (en)

French (fr)

Inventor

D Farge

A Jossin

D Reisdorf

G Ponsinet

Original Assignee

Rhone Poulenc Ind

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.)

1978-12-07

Filing date

1979-12-06

Publication date

1980-07-01

1978-12-07 Priority claimed from FR7834483A external-priority patent/FR2443469A1/fr

1979-10-29 Priority claimed from FR7926732A external-priority patent/FR2468613A2/fr

1979-12-06 Application filed by Rhone Poulenc Ind filed Critical Rhone Poulenc Ind

1980-07-01 Publication of LU81960A1 publication Critical patent/LU81960A1/fr

Links

DBDCNCCRPKTRSD-UHFFFAOYSA-N thieno[3,2-b]pyridine Chemical class C1=CC=C2SC=CC2=N1 DBDCNCCRPKTRSD-UHFFFAOYSA-N 0.000 title claims description 10
238000002360 preparation method Methods 0.000 title claims description 5
229940126601 medicinal product Drugs 0.000 title description 2
239000000203 mixture Substances 0.000 claims description 28
-1 benzylthio Chemical group 0.000 claims description 20
150000003839 salts Chemical class 0.000 claims description 17
238000000034 method Methods 0.000 claims description 13
239000002253 acid Substances 0.000 claims description 9
229910052801 chlorine Inorganic materials 0.000 claims description 6
125000001309 chloro group Chemical group Cl* 0.000 claims description 6
229940125670 thienopyridine Drugs 0.000 claims description 6
239000002175 thienopyridine Substances 0.000 claims description 6
125000004432 carbon atom Chemical group C* 0.000 claims description 5
239000003085 diluting agent Substances 0.000 claims description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 3
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 3
150000007513 acids Chemical class 0.000 claims description 3
239000002671 adjuvant Substances 0.000 claims description 3
125000000217 alkyl group Chemical group 0.000 claims description 3
150000001412 amines Chemical class 0.000 claims description 3
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 3
HSFWRNGVRCDJHI-UHFFFAOYSA-N Acetylene Chemical compound C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 2
150000001450 anions Chemical class 0.000 claims description 2
239000008194 pharmaceutical composition Substances 0.000 claims description 2
239000012458 free base Substances 0.000 claims 1
239000000243 solution Substances 0.000 description 36
239000000047 product Substances 0.000 description 29
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 26
229910052753 mercury Inorganic materials 0.000 description 26
238000001914 filtration Methods 0.000 description 23
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 22
239000007787 solid Substances 0.000 description 19
239000013078 crystal Substances 0.000 description 18
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 17
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 16
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
238000010992 reflux Methods 0.000 description 15
239000000706 filtrate Substances 0.000 description 13
125000001841 imino group Chemical group [H]N=* 0.000 description 12
MKYRMMMSZSVIGD-UHFFFAOYSA-N thieno[3,2-c]pyridine Chemical compound N1=CC=C2SC=CC2=C1 MKYRMMMSZSVIGD-UHFFFAOYSA-N 0.000 description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 11
238000002844 melting Methods 0.000 description 11
230000008018 melting Effects 0.000 description 11
AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 10
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 10
239000000725 suspension Substances 0.000 description 10
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
239000003960 organic solvent Substances 0.000 description 9
GDQBPBMIAFIRIU-UHFFFAOYSA-N thieno[2,3-c]pyridine Chemical compound C1=NC=C2SC=CC2=C1 GDQBPBMIAFIRIU-UHFFFAOYSA-N 0.000 description 9
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
238000006243 chemical reaction Methods 0.000 description 7
229910052938 sodium sulfate Inorganic materials 0.000 description 7
235000011152 sodium sulphate Nutrition 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
239000007864 aqueous solution Substances 0.000 description 6
239000000284 extract Substances 0.000 description 6
239000003921 oil Substances 0.000 description 6
235000019198 oils Nutrition 0.000 description 6
208000002193 Pain Diseases 0.000 description 5
238000009835 boiling Methods 0.000 description 5
230000000202 analgesic effect Effects 0.000 description 4
WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 4
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
229910000027 potassium carbonate Inorganic materials 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
239000000377 silicon dioxide Substances 0.000 description 4
239000002904 solvent Substances 0.000 description 4
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
WTOFYLAWDLQMBZ-UHFFFAOYSA-N 2-azaniumyl-3-thiophen-2-ylpropanoate Chemical compound OC(=O)C(N)CC1=CC=CS1 WTOFYLAWDLQMBZ-UHFFFAOYSA-N 0.000 description 3
PPCCFJRKHNETIK-UHFFFAOYSA-N 6,11-dithia-1-azatricyclo[7.3.0.03,7]dodeca-2,4,7,9-tetraene Chemical compound C1SC=C2C=c3sccc3=CN12 PPCCFJRKHNETIK-UHFFFAOYSA-N 0.000 description 3
241001465754 Metazoa Species 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
241000700159 Rattus Species 0.000 description 3
229920002472 Starch Polymers 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
238000004587 chromatography analysis Methods 0.000 description 3
229910052500 inorganic mineral Inorganic materials 0.000 description 3
235000019359 magnesium stearate Nutrition 0.000 description 3
239000002609 medium Substances 0.000 description 3
239000011707 mineral Substances 0.000 description 3
239000008107 starch Substances 0.000 description 3
235000019698 starch Nutrition 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
ICJKEAGWIQWQKK-UHFFFAOYSA-N 4,11-dithia-1-azatricyclo[7.3.0.03,7]dodeca-2,5,7,9-tetraene Chemical compound S1C=CC2=CC=3N(C=C21)CSC=3 ICJKEAGWIQWQKK-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
241000700605 Viruses Species 0.000 description 2
125000004414 alkyl thio group Chemical group 0.000 description 2
230000003110 anti-inflammatory effect Effects 0.000 description 2
230000001754 anti-pyretic effect Effects 0.000 description 2
230000000840 anti-viral effect Effects 0.000 description 2
239000012736 aqueous medium Substances 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
238000001816 cooling Methods 0.000 description 2
230000000694 effects Effects 0.000 description 2
239000000839 emulsion Substances 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
239000003701 inert diluent Substances 0.000 description 2
150000002540 isothiocyanates Chemical class 0.000 description 2
239000012280 lithium aluminium hydride Substances 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
239000004006 olive oil Substances 0.000 description 2
235000008390 olive oil Nutrition 0.000 description 2
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
239000008247 solid mixture Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
238000002560 therapeutic procedure Methods 0.000 description 2
PZNPLUBHRSSFHT-RRHRGVEJSA-N 1-hexadecanoyl-2-octadecanoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCCCC(=O)O[C@@H](COP([O-])(=O)OCC[N+](C)(C)C)COC(=O)CCCCCCCCCCCCCCC PZNPLUBHRSSFHT-RRHRGVEJSA-N 0.000 description 1
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 1
PQBIJECOZLNVIG-UHFFFAOYSA-N 4,5,6,7-tetrahydrothieno[2,3-c]pyridin-5-ylmethanol Chemical compound C1NC(CO)CC2=C1SC=C2 PQBIJECOZLNVIG-UHFFFAOYSA-N 0.000 description 1
MSDZLUHQKBFCHC-UHFFFAOYSA-N 4,5,6,7-tetrahydrothieno[3,2-b]pyridine Chemical compound C1CCNC2=C1SC=C2 MSDZLUHQKBFCHC-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
235000019489 Almond oil Nutrition 0.000 description 1
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
244000144725 Amygdalus communis Species 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
208000000094 Chronic Pain Diseases 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 description 1
241000709661 Enterovirus Species 0.000 description 1
241000430519 Human rhinovirus sp. Species 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-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
240000006240 Linum usitatissimum Species 0.000 description 1
101100004031 Mus musculus Aven gene Proteins 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
206010028980 Neoplasm Diseases 0.000 description 1
240000007817 Olea europaea Species 0.000 description 1
239000005662 Paraffin oil Substances 0.000 description 1
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
239000002202 Polyethylene glycol Substances 0.000 description 1
208000025747 Rheumatic disease Diseases 0.000 description 1
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
201000002661 Spondylitis Diseases 0.000 description 1
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
229930006000 Sucrose Natural products 0.000 description 1
230000001154 acute effect Effects 0.000 description 1
208000005298 acute pain Diseases 0.000 description 1
230000007059 acute toxicity Effects 0.000 description 1
231100000403 acute toxicity Toxicity 0.000 description 1
235000004279 alanine Nutrition 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
239000008168 almond oil Substances 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
239000002260 anti-inflammatory agent Substances 0.000 description 1
229940121363 anti-inflammatory agent Drugs 0.000 description 1
230000002128 anti-rhinoviral effect Effects 0.000 description 1
239000003443 antiviral agent Substances 0.000 description 1
239000012300 argon atmosphere Substances 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
201000011510 cancer Diseases 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
238000004113 cell culture Methods 0.000 description 1
230000000973 chemotherapeutic effect Effects 0.000 description 1
239000012320 chlorinating reagent Substances 0.000 description 1
229940110456 cocoa butter Drugs 0.000 description 1
235000019868 cocoa butter Nutrition 0.000 description 1
239000003240 coconut oil Substances 0.000 description 1
235000019864 coconut oil Nutrition 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
230000000120 cytopathologic effect Effects 0.000 description 1
238000010908 decantation Methods 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
239000003814 drug Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 description 1
229940093471 ethyl oleate Drugs 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
210000002950 fibroblast Anatomy 0.000 description 1
239000007789 gas Substances 0.000 description 1
239000007903 gelatin capsule Substances 0.000 description 1
239000008187 granular material Substances 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
208000027866 inflammatory disease Diseases 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
239000002198 insoluble material Substances 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
125000001810 isothiocyanato group Chemical group *N=C=S 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000008101 lactose Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
SIAPCJWMELPYOE-UHFFFAOYSA-N lithium hydride Chemical compound [LiH] SIAPCJWMELPYOE-UHFFFAOYSA-N 0.000 description 1
229910000103 lithium hydride Inorganic materials 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
239000000155 melt Substances 0.000 description 1
MBXNQZHITVCSLJ-UHFFFAOYSA-N methyl fluorosulfonate Chemical compound COS(F)(=O)=O MBXNQZHITVCSLJ-UHFFFAOYSA-N 0.000 description 1
210000002850 nasal mucosa Anatomy 0.000 description 1
238000002663 nebulization Methods 0.000 description 1
230000000926 neurological effect Effects 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
231100000065 noncytotoxic Toxicity 0.000 description 1
230000002020 noncytotoxic effect Effects 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
239000002674 ointment Substances 0.000 description 1
150000002895 organic esters Chemical class 0.000 description 1
201000008482 osteoarthritis Diseases 0.000 description 1
GNWXVOQHLPBSSR-UHFFFAOYSA-N oxolane;toluene Chemical compound C1CCOC1.CC1=CC=CC=C1 GNWXVOQHLPBSSR-UHFFFAOYSA-N 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
238000000053 physical method Methods 0.000 description 1
239000006187 pill Substances 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
230000002335 preservative effect Effects 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
210000002345 respiratory system Anatomy 0.000 description 1
230000000552 rheumatic effect Effects 0.000 description 1
201000003068 rheumatic fever Diseases 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000008347 soybean phospholipid Substances 0.000 description 1
239000008174 sterile solution Substances 0.000 description 1
230000001954 sterilising effect Effects 0.000 description 1
238000004659 sterilization and disinfection Methods 0.000 description 1
239000003206 sterilizing agent Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000003760 tallow Substances 0.000 description 1
230000029305 taxis Effects 0.000 description 1
QPJXOAAERYCQJF-UHFFFAOYSA-N thieno[2,3-c]pyridine;hydrochloride Chemical compound Cl.C1=NC=C2SC=CC2=C1 QPJXOAAERYCQJF-UHFFFAOYSA-N 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
230000000472 traumatic effect Effects 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
239000003981 vehicle Substances 0.000 description 1
230000003612 virological effect Effects 0.000 description 1
208000009935 visceral pain Diseases 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000001993 wax Substances 0.000 description 1
238000009736 wetting Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains three hetero rings
- C07D513/14—Ortho-condensed systems

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

LU81960A 1978-12-07 1979-12-06 Nouveaux derives de la thienopyridine,leur preparation et les medicaments qui les contiennent LU81960A1 (fr)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
FR7834483A FR2443469A1 (fr)	1978-12-07	1978-12-07	Nouveaux derives de la thienopyridine, leur preparation et les medicaments qui les contiennent
FR7834483		1978-12-07
FR7926732A FR2468613A2 (fr)	1979-10-29	1979-10-29	Nouveaux derives de la thienopyridine, leur preparation et les medicaments qui les contiennent
FR7926732		1979-10-29

Publications (1)

Publication Number	Publication Date
LU81960A1 true LU81960A1 (fr)	1980-07-01

Family

ID=26220895

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
LU81960A LU81960A1 (fr)	1978-12-07	1979-12-06	Nouveaux derives de la thienopyridine,leur preparation et les medicaments qui les contiennent

Country Status (7)

Country	Link
US (1)	US4261999A (it)
DE (1)	DE2949399A1 (it)
DK (1)	DK520379A (it)
GB (1)	GB2038330A (it)
IT (1)	IT1126569B (it)
LU (1)	LU81960A1 (it)
NL (1)	NL7908655A (it)

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
HU170680B (it) *	1973-05-30	1977-08-28
NL169076C (nl) *	1975-08-06	1982-06-01	Rhone Poulenc Ind	Werkwijze voor het bereiden of vervaardigen van farmacologische preparaten met een analgetische en antipyretische werking, alsmede werkwijze voor het bereiden van geneeskrachtige verbindingen, welke geschikt zijn voor gebruik in dergelijke preparaten.
FR2378030A1 (fr) *	1977-01-20	1978-08-18	Rhone Poulenc Ind	Nouveau derive de l'isoquinoleine, sa preparation et les compositions qui le contiennent
NL7800383A (nl) *	1977-01-20	1978-07-24	Rhone Poulenc Ind	Nieuwe isochinolinederivaten, de bereiding ervan en preparaten die de isochinolinederivaten bevatten.

1979
- 1979-11-29 NL NL7908655A patent/NL7908655A/nl not_active Application Discontinuation
- 1979-12-05 GB GB7942043A patent/GB2038330A/en not_active Withdrawn
- 1979-12-05 US US06/100,523 patent/US4261999A/en not_active Expired - Lifetime
- 1979-12-06 DK DK520379A patent/DK520379A/da unknown
- 1979-12-06 LU LU81960A patent/LU81960A1/fr unknown
- 1979-12-07 IT IT27999/79A patent/IT1126569B/it active
- 1979-12-07 DE DE19792949399 patent/DE2949399A1/de not_active Withdrawn

Also Published As

Publication number	Publication date
IT7927999A0 (it)	1979-12-07
GB2038330A (en)	1980-07-23
DK520379A (da)	1980-06-08
US4261999A (en)	1981-04-14
DE2949399A1 (de)	1980-06-26
NL7908655A (nl)	1980-06-10
IT1126569B (it)	1986-05-21

Publication	Publication Date	Title
CA1294967C (fr)	1992-01-28	Derives du 1h, 3h-pyrrolo [1,2-c] thiazole, leur preparation et les compositions pharmaceutiques qui les contiennent
FR2663633A1 (fr)	1991-12-27	Nouvelles chalcones, leur procede de preparation et les compositions pharmaceutiques qui les contiennent.
EP0253711A1 (fr)	1988-01-20	Nouveaux dérivés du 1H,3H-Pyrrolo [1,2-c] thiazole, leur préparation et les Compositions pharmaceutiques qui les contiennent
CA2012343A1 (fr)	1990-09-17	Derives du 1h, 3h-pyrrolo, (1,2-c) thiazolecarboxamide-7, leur preparation et les compositions pharmaceutiques qui les contiennent
EP0147317A2 (fr)	1985-07-03	Nouveaux dérivés ortho-condensés du pyrrole, leur préparation et les médicaments qui les contiennent
EP0374040A1 (fr)	1990-06-20	Dérivés de l'imino-2 Benzothiazoline, leurs procédés de préparation et les médicaments les contenant
FR2662695A1 (fr)	1991-12-06	Amino-2 polyfluoroalcoxy-6 benzoselenazoles, leur preparation et les medicaments les contenant.
FR2541280A1 (fr)	1984-08-24	Nouveaux derives du 1h, 3h-pyrrolo (1,2c) thiazolecarboxamide-7, leur preparation et les medicaments qui les contiennent
EP0374041A1 (fr)	1990-06-20	Médicaments à base de dérivés de la benzothiazolamine-2, dérivés et leur préparation
FR2663331A1 (fr)	1991-12-20	Nouveaux derives de l'oxazole, leur preparation et les compositions pharmaceutiques qui les contiennent.
CH633010A5 (fr)	1982-11-15	Derives de l'isoquinoleine, leur preparation et medicament qui les contient.
EP0124384B1 (fr)	1987-08-05	Nouveaux dérivés du pyrrole orthocondensé utiles pour la préparation de nouveaux médicaments et leur préparation
EP0099770B1 (fr)	1986-08-27	Nouveaux dérivés d'oxazinobenzothiazine-6,6-dioxyde, leur préparation et leur application en tant que médicaments
EP0045251B1 (fr)	1983-11-30	Nouveaux dérivés de la thiazolo (3,2-a) pyrimidine, leur préparation et les médicaments qui les contiennent
CA1112642A (fr)	1981-11-17	Derives de l'isoquinoleine, leur preparation et les compositions qui les contiennent
EP0408437B1 (fr)	1994-06-08	Dérivés d'alkylimino-2 benzothiazoline, leurs procédés de préparation et les médicaments les contenant
LU81960A1 (fr)	1980-07-01	Nouveaux derives de la thienopyridine,leur preparation et les medicaments qui les contiennent
CA1073912A (fr)	1980-03-18	Derives de la dibenzo (de,h) quinoleine, leur preparation et les compositions qui les contiennent
WO1992021665A1 (fr)	1992-12-10	Nouveaux derives de l'oxazole et leur preparation
CA1155117A (fr)	1983-10-11	Derives de l'isoquinoleine, leur preparation et les medicaments qui les contiennent
EP0517590A1 (fr)	1992-12-09	Nouveaux dérivés de l'oxazole, leur préparation et les compositions qui les contiennent
CH626371A5 (it)	1981-11-13
EP0528968A1 (fr)	1993-03-03	Derives d'(alkylthio-3 propyl)-3 benzothiazoline, leur preparation et les medicaments les contenant.
EP0027085B1 (fr)	1983-12-14	Nouveaux dérivés de la thiazolo (3,2-c) benzoxazine-1,3, leur préparation et les médicaments qui les contiennent
CH625249A5 (en)	1981-09-15	Process for the preparation of imidazothiazole derivatives