BE897247A - Nouveau composes heterocycliques - Google Patents

Nouveau composes heterocycliques Download PDF

Info

Publication number: BE897247A
Authority: BE; Belgium
Prior art keywords: group; alkyl; amino; hydrogen; thiadiazol
Prior art date: 1982-07-08

Application number

BE0/211139A

Other languages

English (en)

French (fr)

Original Assignee

Glaxo Group Ltd

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.)

1982-07-08

Filing date

1983-07-08

Publication date

1984-01-09

1983-07-08 Application filed by Glaxo Group Ltd filed Critical Glaxo Group Ltd

1984-01-09 Publication of BE897247A publication Critical patent/BE897247A/fr

Links

150000002391 heterocyclic compounds Chemical class 0.000 title abstract description 5
125000002947 alkylene group Chemical group 0.000 claims abstract description 3
150000001875 compounds Chemical class 0.000 claims description 67
-1 aloxy Chemical group 0.000 claims description 35
229910052717 sulfur Inorganic materials 0.000 claims description 32
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 31
229910052739 hydrogen Inorganic materials 0.000 claims description 30
239000001257 hydrogen Substances 0.000 claims description 30
125000000217 alkyl group Chemical group 0.000 claims description 25
238000000034 method Methods 0.000 claims description 24
150000003839 salts Chemical class 0.000 claims description 19
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 18
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
238000002360 preparation method Methods 0.000 claims description 14
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 12
KFZMGEQAYNKOFK-UHFFFAOYSA-N 2-propanol Substances CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 11
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
239000002253 acid Substances 0.000 claims description 10
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 9
125000002252 acyl group Chemical group 0.000 claims description 9
150000004985 diamines Chemical class 0.000 claims description 9
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
239000002904 solvent Substances 0.000 claims description 9
125000000753 cycloalkyl group Chemical group 0.000 claims description 8
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 7
125000000304 alkynyl group Chemical group 0.000 claims description 7
125000005842 heteroatom Chemical group 0.000 claims description 7
229910052757 nitrogen Inorganic materials 0.000 claims description 7
125000003545 alkoxy group Chemical group 0.000 claims description 6
125000003282 alkyl amino group Chemical group 0.000 claims description 6
125000004432 carbon atom Chemical group C* 0.000 claims description 6
150000004677 hydrates Chemical class 0.000 claims description 6
239000012453 solvate Substances 0.000 claims description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
125000003342 alkenyl group Chemical group 0.000 claims description 5
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
125000004475 heteroaralkyl group Chemical group 0.000 claims description 5
125000001072 heteroaryl group Chemical group 0.000 claims description 5
229910052760 oxygen Inorganic materials 0.000 claims description 5
239000001301 oxygen Substances 0.000 claims description 5
239000008194 pharmaceutical composition Substances 0.000 claims description 5
ITRWFUDFSUBHQU-UHFFFAOYSA-N 1-[(4-amino-1,2,5-thiadiazol-3-yl)amino]-3-[3-(piperidin-1-ylmethyl)phenoxy]propan-2-ol Chemical compound NC=1C(=NSN1)NCC(COC1=CC(=CC=C1)CN1CCCCC1)O ITRWFUDFSUBHQU-UHFFFAOYSA-N 0.000 claims description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 4
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 4
150000001412 amines Chemical class 0.000 claims description 4
125000003710 aryl alkyl group Chemical group 0.000 claims description 4
RCCPEORTSYDPMB-UHFFFAOYSA-N hydroxy benzenecarboximidothioate Chemical compound OSC(=N)C1=CC=CC=C1 RCCPEORTSYDPMB-UHFFFAOYSA-N 0.000 claims description 4
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 4
125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
239000000546 pharmaceutical excipient Substances 0.000 claims description 4
125000004076 pyridyl group Chemical group 0.000 claims description 4
125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 3
125000004663 dialkyl amino group Chemical group 0.000 claims description 3
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 3
239000004615 ingredient Substances 0.000 claims description 3
125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 2
YJMNDSUCTVXHFM-UHFFFAOYSA-N 1-[[4-(2-methoxyethylamino)-1,2,5-thiadiazol-3-yl]amino]-3-[3-(piperidin-1-ylmethyl)phenoxy]propan-2-ol Chemical compound COCCNC=1C(=NSN1)NCC(COC1=CC(=CC=C1)CN1CCCCC1)O YJMNDSUCTVXHFM-UHFFFAOYSA-N 0.000 claims description 2
108010011222 cyclo(Arg-Pro) Chemical group 0.000 claims description 2
239000003937 drug carrier Substances 0.000 claims description 2
125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims description 2
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 2
125000004430 oxygen atom Chemical group O* 0.000 claims description 2
125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 claims description 2
125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims description 2
229920006395 saturated elastomer Polymers 0.000 claims description 2
125000004354 sulfur functional group Chemical group 0.000 claims description 2
125000004950 trifluoroalkyl group Chemical group 0.000 claims description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
101000916237 Schizosaccharomyces pombe (strain 972 / ATCC 24843) Cullin-3 Proteins 0.000 claims 2
HXKKHQJGJAFBHI-UHFFFAOYSA-N 1-aminopropan-2-ol Chemical compound CC(O)CN HXKKHQJGJAFBHI-UHFFFAOYSA-N 0.000 claims 1
102000000543 Histamine Receptors Human genes 0.000 abstract description 3
108010002059 Histamine Receptors Proteins 0.000 abstract description 3
230000000694 effects Effects 0.000 abstract description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 63
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 33
239000000243 solution Substances 0.000 description 32
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 27
239000000203 mixture Substances 0.000 description 24
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
239000007787 solid Substances 0.000 description 17
229940126062 Compound A Drugs 0.000 description 15
NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 15
239000006260 foam Substances 0.000 description 13
229910021529 ammonia Inorganic materials 0.000 description 12
LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 12
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
238000006243 chemical reaction Methods 0.000 description 10
239000000725 suspension Substances 0.000 description 10
229960004592 isopropanol Drugs 0.000 description 9
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
239000003826 tablet Substances 0.000 description 8
238000004587 chromatography analysis Methods 0.000 description 7
239000012043 crude product Substances 0.000 description 7
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
238000004128 high performance liquid chromatography Methods 0.000 description 6
239000000047 product Substances 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
239000004480 active ingredient Substances 0.000 description 5
239000000543 intermediate Substances 0.000 description 5
238000003756 stirring Methods 0.000 description 5
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 4
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
241000700159 Rattus Species 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 4
239000000843 powder Substances 0.000 description 4
210000002784 stomach Anatomy 0.000 description 4
239000000126 substance Substances 0.000 description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
238000001802 infusion Methods 0.000 description 3
238000002347 injection Methods 0.000 description 3
239000007924 injection Substances 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 2
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
KESHAMUNPHJULK-UHFFFAOYSA-N 4-methoxy-1,2,5-thiadiazol-3-amine Chemical compound COC1=NSN=C1N KESHAMUNPHJULK-UHFFFAOYSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 2
125000004414 alkyl thio group Chemical group 0.000 description 2
230000000172 allergic effect Effects 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
208000010668 atopic eczema Diseases 0.000 description 2
239000002585 base Substances 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
238000009472 formulation Methods 0.000 description 2
239000012458 free base Substances 0.000 description 2
125000002541 furyl group Chemical group 0.000 description 2
230000002496 gastric effect Effects 0.000 description 2
FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 2
229960001340 histamine Drugs 0.000 description 2
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 2
238000010253 intravenous injection Methods 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 2
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
230000003287 optical effect Effects 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
238000010992 reflux Methods 0.000 description 2
230000028327 secretion Effects 0.000 description 2
239000012279 sodium borohydride Substances 0.000 description 2
229910000033 sodium borohydride Inorganic materials 0.000 description 2
239000003381 stabilizer Substances 0.000 description 2
238000010561 standard procedure Methods 0.000 description 2
239000000829 suppository Substances 0.000 description 2
238000012360 testing method Methods 0.000 description 2
230000000699 topical effect Effects 0.000 description 2
125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
CXXAVVLINHMIJN-UHFFFAOYSA-N 1-[(4-amino-1,2,5-thiadiazol-3-yl)amino]-3-[3-[(dimethylamino)methyl]phenoxy]propan-2-ol Chemical compound NC=1C(=NSN1)NCC(COC1=CC(=CC=C1)CN(C)C)O CXXAVVLINHMIJN-UHFFFAOYSA-N 0.000 description 1
HMUNWXXNJPVALC-UHFFFAOYSA-N 1-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C(CN1CC2=C(CC1)NN=N2)=O HMUNWXXNJPVALC-UHFFFAOYSA-N 0.000 description 1
ZXZMYKUDDJHDGK-UHFFFAOYSA-N 1-amino-4-[3-(piperidin-1-ylmethyl)phenoxy]butan-2-ol Chemical compound NCC(O)CCOC1=CC=CC(CN2CCCCC2)=C1 ZXZMYKUDDJHDGK-UHFFFAOYSA-N 0.000 description 1
125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
BTANRVKWQNVYAZ-UHFFFAOYSA-N 2-butanol Substances CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 1
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
ASUDFOJKTJLAIK-UHFFFAOYSA-N 2-methoxyethanamine Chemical compound COCCN ASUDFOJKTJLAIK-UHFFFAOYSA-N 0.000 description 1
125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
125000006321 2-propynyl amino group Chemical group [H]C#CC([H])([H])N([H])* 0.000 description 1
125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
JGUPTNIZOBZUON-UHFFFAOYSA-N 3,4-dimethoxy-1,2,5-thiadiazole Chemical compound COC1=NSN=C1OC JGUPTNIZOBZUON-UHFFFAOYSA-N 0.000 description 1
CDHKCMVEGUQUCN-UHFFFAOYSA-N 3,4-dimethoxy-1,2,5-thiadiazole 1-oxide Chemical compound COC1=NS(=O)N=C1OC CDHKCMVEGUQUCN-UHFFFAOYSA-N 0.000 description 1
ORZIHESPONWBAJ-UHFFFAOYSA-N 3-(1,3-dioxolan-2-yl)phenol Chemical compound OC1=CC=CC(C2OCCO2)=C1 ORZIHESPONWBAJ-UHFFFAOYSA-N 0.000 description 1
QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 description 1
GRKAHHLMHHQOQY-UHFFFAOYSA-N 4-methoxy-n,n-dimethyl-1,1-dioxo-1,2,5-thiadiazol-3-amine Chemical compound COC1=NS(=O)(=O)N=C1N(C)C GRKAHHLMHHQOQY-UHFFFAOYSA-N 0.000 description 1
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
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229940122957 Histamine H2 receptor antagonist Drugs 0.000 description 1
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FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
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AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical class CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
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QGMRQYFBGABWDR-UHFFFAOYSA-M Pentobarbital sodium Chemical compound [Na+].CCCC(C)C1(CC)C(=O)NC(=O)[N-]C1=O QGMRQYFBGABWDR-UHFFFAOYSA-M 0.000 description 1
208000008469 Peptic Ulcer Diseases 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
229960000583 acetic acid Drugs 0.000 description 1
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239000002671 adjuvant Substances 0.000 description 1
125000003172 aldehyde group Chemical group 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
150000008041 alkali metal carbonates Chemical class 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
125000000278 alkyl amino alkyl group Chemical group 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
125000004103 aminoalkyl group Chemical group 0.000 description 1
230000003444 anaesthetic effect Effects 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
239000005557 antagonist Substances 0.000 description 1
239000008135 aqueous vehicle Substances 0.000 description 1
125000003435 aroyl group Chemical group 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
150000001558 benzoic acid derivatives Chemical class 0.000 description 1
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 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
230000000903 blocking effect Effects 0.000 description 1
239000000337 buffer salt Substances 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000002775 capsule Substances 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
150000001860 citric acid derivatives Chemical class 0.000 description 1
229940110456 cocoa butter Drugs 0.000 description 1
235000019868 cocoa butter Nutrition 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
230000001143 conditioned effect Effects 0.000 description 1
230000008602 contraction Effects 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000006071 cream Substances 0.000 description 1
239000013078 crystal Substances 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000004985 dialkyl amino alkyl group Chemical group 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
239000003814 drug Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
239000007920 enema Substances 0.000 description 1
229940079360 enema for constipation Drugs 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
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
DDRPCXLAQZKBJP-UHFFFAOYSA-N furfurylamine Chemical compound NCC1=CC=CO1 DDRPCXLAQZKBJP-UHFFFAOYSA-N 0.000 description 1
239000007789 gas Substances 0.000 description 1
210000004211 gastric acid Anatomy 0.000 description 1
230000027119 gastric acid secretion Effects 0.000 description 1
239000000499 gel Substances 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
239000011521 glass Substances 0.000 description 1
125000005456 glyceride group Chemical group 0.000 description 1
229940093915 gynecological organic acid Drugs 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
230000009931 harmful effect Effects 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
125000002768 hydroxyalkyl group Chemical group 0.000 description 1
229940031574 hydroxymethyl cellulose Drugs 0.000 description 1
125000002883 imidazolyl group Chemical group 0.000 description 1
230000004968 inflammatory condition Effects 0.000 description 1
230000002757 inflammatory effect Effects 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
239000013067 intermediate product Substances 0.000 description 1
239000012280 lithium aluminium hydride Substances 0.000 description 1
239000006210 lotion Substances 0.000 description 1
239000007937 lozenge Substances 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
230000014759 maintenance of location Effects 0.000 description 1
150000002688 maleic acid derivatives Chemical class 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
239000011707 mineral Substances 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
125000002950 monocyclic group Chemical group 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
239000002674 ointment Substances 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
230000010412 perfusion Effects 0.000 description 1
XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
150000003141 primary amines Chemical class 0.000 description 1
JKANAVGODYYCQF-UHFFFAOYSA-N prop-2-yn-1-amine Chemical compound NCC#C JKANAVGODYYCQF-UHFFFAOYSA-N 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
230000000069 prophylactic effect Effects 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
HDOUGSFASVGDCS-UHFFFAOYSA-N pyridin-3-ylmethanamine Chemical compound NCC1=CC=CN=C1 HDOUGSFASVGDCS-UHFFFAOYSA-N 0.000 description 1
JUJWROOIHBZHMG-RALIUCGRSA-N pyridine-d5 Chemical compound [2H]C1=NC([2H])=C([2H])C([2H])=C1[2H] JUJWROOIHBZHMG-RALIUCGRSA-N 0.000 description 1
239000002510 pyrogen Substances 0.000 description 1
125000000168 pyrrolyl group Chemical group 0.000 description 1
238000012797 qualification Methods 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
210000005245 right atrium Anatomy 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
239000007921 spray Substances 0.000 description 1
230000000087 stabilizing effect Effects 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000008223 sterile water Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
150000003890 succinate salts Chemical class 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
150000003892 tartrate salts Chemical class 0.000 description 1
238000003419 tautomerization reaction Methods 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
125000000335 thiazolyl group Chemical group 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
239000003981 vehicle Substances 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/10—1,2,5-Thiadiazoles; Hydrogenated 1,2,5-thiadiazoles
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D317/28—Radicals substituted by nitrogen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Veterinary Medicine (AREA)
Life Sciences & Earth Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Public Health (AREA)
Medicinal Chemistry (AREA)
General Health & Medical Sciences (AREA)
Immunology (AREA)
Pulmonology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)

BE0/211139A 1982-07-08 1983-07-08 Nouveau composes heterocycliques BE897247A (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB8219746		1982-07-08

Publications (1)

Publication Number	Publication Date
BE897247A true BE897247A (fr)	1984-01-09

Family

ID=10531541

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
BE0/211139A BE897247A (fr)	1982-07-08	1983-07-08	Nouveau composes heterocycliques

Country Status (11)

Country	Link
JP (1)	JPS5927880A (da)
AU (1)	AU1666583A (da)
BE (1)	BE897247A (da)
DE (1)	DE3324771A1 (da)
DK (1)	DK317283A (da)
FR (1)	FR2532937A1 (da)
GB (1)	GB2124622A (da)
IT (1)	IT8348653A0 (da)
NL (1)	NL8302450A (da)
SE (1)	SE8303913L (da)
ZA (1)	ZA835009B (da)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4567191A (en) *	1983-06-07	1986-01-28	Merck & Co., Inc.	Amino-phenyl-thiadiazoledioxides as gastric secretion inhibitors
DE3326545A1 (de) *	1983-07-22	1985-01-31	Ludwig Heumann & Co GmbH, 8500 Nürnberg	Propan-2-ol-derivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel
DE3408327A1 (de) *	1984-03-07	1985-09-12	Ludwig Heumann & Co GmbH, 8500 Nürnberg	Diaminderivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel
DE60326080D1 (en)	2002-10-09	2009-03-19	Schering Corp	Thiadiazoldioxide und thiadiazoloxide als cxc- und cc-chemokinrezeptor liganden
ES2308299T3 (es)	2003-12-19	2008-12-01	Schering Corp	Tiadiazoles como ligandos de receptores de cxc-y cc-quimioquinas.
EP1697354B1 (en)	2003-12-22	2013-08-07	Merck Sharp & Dohme Corp.	Isothiazole dioxides as cxc- and cc- chemokine receptor ligands
DE602006017849D1 (de)	2005-06-29	2010-12-09	Schering Corp	5,6-disubstituierte oxadiazolopyrazine und thiadiazolopyrazine als liganden des cxc-chemokinrezeptors
MX2008000366A (es)	2005-06-29	2008-03-07	Schering Corp	Oxadiazoles di-sustituidos como ligandos del receptor cxc-quimiocina.
EP4196793A1 (en)	2020-08-11	2023-06-21	Université de Strasbourg	H2 blockers targeting liver macrophages for the prevention and treatment of liver disease and cancer

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0040696B1 (en) *	1980-04-30	1986-08-27	Merck & Co. Inc.	Aminothiadiazoles as gastric secretion inhibitors
US4411899A (en) *	1981-12-21	1983-10-25	Merck & Co., Inc.	Substituted derivatives of amino alkane diols as gastric secretion inhibitors

1983
- 1983-07-08 JP JP58124554A patent/JPS5927880A/ja active Pending
- 1983-07-08 FR FR8311402A patent/FR2532937A1/fr not_active Withdrawn
- 1983-07-08 SE SE8303913A patent/SE8303913L/xx not_active Application Discontinuation
- 1983-07-08 IT IT8348653A patent/IT8348653A0/it unknown
- 1983-07-08 DE DE19833324771 patent/DE3324771A1/de not_active Withdrawn
- 1983-07-08 GB GB08318525A patent/GB2124622A/en not_active Withdrawn
- 1983-07-08 AU AU16665/83A patent/AU1666583A/en not_active Abandoned
- 1983-07-08 NL NL8302450A patent/NL8302450A/nl not_active Application Discontinuation
- 1983-07-08 ZA ZA835009A patent/ZA835009B/xx unknown
- 1983-07-08 BE BE0/211139A patent/BE897247A/fr not_active IP Right Cessation
- 1983-07-08 DK DK317283A patent/DK317283A/da not_active Application Discontinuation

Also Published As

Publication number	Publication date
ZA835009B (en)	1985-02-27
SE8303913L (sv)	1984-01-09
GB8318525D0 (en)	1983-08-10
DK317283D0 (da)	1983-07-08
IT8348653A0 (it)	1983-07-08
DE3324771A1 (de)	1984-01-12
SE8303913D0 (sv)	1983-07-08
NL8302450A (nl)	1984-02-01
AU1666583A (en)	1984-01-12
GB2124622A (en)	1984-02-22
FR2532937A1 (fr)	1984-03-16
JPS5927880A (ja)	1984-02-14
DK317283A (da)	1984-01-09

Publication	Publication Date	Title
EP1720848B1 (fr)	2007-12-05	Derives de alkylpiperazine- et alkylhomopiperazine- carboxylates, leur preparation et leur application en tant qu'inhibiteurs de l'enzyme faah
LU84561A1 (fr)	1983-09-08	2-(4-((4,4,-dialcoyl-2,6-piperidinedione-1-yl)butyl)-1-piperazinyl)pyrimidines
CA2552565C (fr)	2013-12-31	Derives de type aryloxyalkylcarbamates, leur preparation et leur application en therapeutique
FR2639942A1 (fr)	1990-06-08	Ethers oximes de propenone, procede pour leur preparation et compositions pharmaceutiques les contenant
BE897247A (fr)	1984-01-09	Nouveau composes heterocycliques
EP0576619B1 (fr)	1995-01-25	Compositions therapeutiques a base de derives de 1,2-dithiole-3-thione
US4139538A (en)	1979-02-13	Oxazolidinones as therapeutic agents
CH655104A5 (fr)	1986-03-27	Derives heterocycliques triazoliques, procedes pour leur preparation et compositions pharmaceutiques les comportant.
EP0115979A1 (fr)	1984-08-15	Nouveaux dérivés du 1H,3H-pyrrolo (1,2-c) thiazole leur préparation et les médicaments qui les contiennent
EP0049049B1 (en)	1985-11-13	5-amino-tetrazole derivatives, processes for their preparation and pharmaceutical compositions containing them
JPH032116A (ja)	1991-01-08	ベンゼン誘導体、その調製およびこれを含有する薬学的組成物
EP1966167B1 (fr)	2010-06-16	Derives diaryltriazolmethylamine, leur preparation et leur application en therapeutique.
EP0101380A2 (fr)	1984-02-22	Nicotinamide 1-oxyde N-substitué, ses sels, procédé pour leur préparation et compositions pharmaceutiques en contenant
JPH0446953B2 (da)	1992-07-31
FR2464259A1 (fr)	1981-03-06	Nouvelles 5-(2-chlorophenyl)-6h-1,3,4-thiadiazine-2-amines, utiles notamment comme anticonvulsivants, et leur procede de preparation
FR2516510A1 (fr)	1983-05-20	Derives de la (trimethoxy-3,4,5-cinnamoyl)-1-aminocarbonylethyl-4-piperazine substituee utilisables en pharmacie et procede pour leur preparation
US4507296A (en)	1985-03-26	Tetrazoles, pharmaceutical use and compositions
FR2719047A1 (fr)	1995-10-27	Nouveaux dérivés de benzylamines, leur procédé de fabrication et les compositions pharmaceutiques les renfermant.
FR2521993A1 (fr)	1983-08-26	Composes heterocycliques azotes, leur preparation et leur utilisation therapeutique en tant qu'antagonistes de l'histamine
EP0234971A1 (fr)	1987-09-02	Nouveaux amides substitues, leur preparation et les compositions pharmaceutiques qui les contiennent
BE898403A (fr)	1984-06-06	Nouveaux derives d'ethene-diamine et de guanidine.
EP0082058A1 (fr)	1983-06-22	Ethers d'oximes de pyridyl-1 pentanone-3, leur procédé de préparation et leur utilisation comme médicament
US4585781A (en)	1986-04-29	Heterocyclic derivatives
FR2508445A1 (fr)	1982-12-31	Nouveaux derives de benzoyl-phenyl-piperidine, leur procede de preparation et leur application, notamment en therapeutique
ITMI990456A1 (it)	2000-09-05	Composti eterociclici ad attivita' antitumorale

Legal Events

Date	Code	Title	Description
1987-01-31	RE	Patent lapsed	Owner name: GLAXO GROUP LTD Effective date: 19860731

Date

Code

Title

Description

1987-01-31

Patent lapsed

Owner name: GLAXO GROUP LTD

Effective date: 19860731