LU86487A1 - Nouveaux derives du thiazole,leur preparation et leur utilisation en therapeutique - Google Patents

Nouveaux derives du thiazole,leur preparation et leur utilisation en therapeutique Download PDF

Info

Publication number: LU86487A1
Authority: LU; Luxembourg
Prior art keywords: group; formula; alkyl; compound; phenyl
Prior art date: 1985-06-22

Application number

LU86487A

Other languages

English (en)

French (fr)

Original Assignee

Sandoz Sa

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1985-06-22

Filing date

1986-06-20

Publication date

1987-01-13

1986-06-20 Application filed by Sandoz Sa filed Critical Sandoz Sa

1987-01-13 Publication of LU86487A1 publication Critical patent/LU86487A1/fr

Links

150000007979 thiazole derivatives Chemical class 0.000 title claims description 10
239000003814 drug Substances 0.000 title claims description 5
238000002360 preparation method Methods 0.000 title claims description 4
150000001875 compounds Chemical class 0.000 claims description 86
229910052739 hydrogen Inorganic materials 0.000 claims description 51
239000001257 hydrogen Substances 0.000 claims description 49
-1 trimethylene, tetramethylene Chemical group 0.000 claims description 38
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 36
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 34
239000002253 acid Substances 0.000 claims description 22
150000003839 salts Chemical class 0.000 claims description 22
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 21
229910052799 carbon Inorganic materials 0.000 claims description 17
125000004432 carbon atom Chemical group C* 0.000 claims description 16
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 15
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 12
238000000034 method Methods 0.000 claims description 12
125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims description 12
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 10
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 10
229910002091 carbon monoxide Inorganic materials 0.000 claims description 9
239000012458 free base Substances 0.000 claims description 9
125000000217 alkyl group Chemical group 0.000 claims description 8
125000002947 alkylene group Chemical group 0.000 claims description 8
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 8
229910052736 halogen Inorganic materials 0.000 claims description 6
150000002367 halogens Chemical class 0.000 claims description 6
230000008569 process Effects 0.000 claims description 6
125000004450 alkenylene group Chemical group 0.000 claims description 5
239000003795 chemical substances by application Substances 0.000 claims description 5
229910052757 nitrogen Inorganic materials 0.000 claims description 5
125000001424 substituent group Chemical group 0.000 claims description 5
125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims description 5
125000004419 alkynylene group Chemical group 0.000 claims description 4
230000001430 anti-depressive effect Effects 0.000 claims description 4
230000002932 anti-schizophrenic effect Effects 0.000 claims description 4
239000002249 anxiolytic agent Substances 0.000 claims description 4
125000000753 cycloalkyl group Chemical group 0.000 claims description 4
125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 4
150000007513 acids Chemical class 0.000 claims description 3
239000000935 antidepressant agent Substances 0.000 claims description 3
230000000949 anxiolytic effect Effects 0.000 claims description 3
239000003085 diluting agent Substances 0.000 claims description 3
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
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 claims description 3
229940005513 antidepressants Drugs 0.000 claims description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
239000008194 pharmaceutical composition Substances 0.000 claims description 2
239000000126 substance Substances 0.000 claims 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 37
239000000203 mixture Substances 0.000 description 25
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
239000000460 chlorine Substances 0.000 description 19
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
238000002844 melting Methods 0.000 description 14
230000008018 melting Effects 0.000 description 14
239000000243 solution Substances 0.000 description 14
239000012071 phase Substances 0.000 description 12
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 11
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 8
239000000155 melt Substances 0.000 description 8
230000000694 effects Effects 0.000 description 7
238000003756 stirring Methods 0.000 description 7
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
150000001721 carbon Chemical group 0.000 description 6
239000011976 maleic acid Substances 0.000 description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
230000003997 social interaction Effects 0.000 description 6
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 5
229910052801 chlorine Inorganic materials 0.000 description 5
238000007796 conventional method Methods 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
230000036626 alertness Effects 0.000 description 4
150000002431 hydrogen Chemical class 0.000 description 4
239000002904 solvent Substances 0.000 description 4
239000007858 starting material Substances 0.000 description 4
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
241000699670 Mus sp. Species 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
239000000284 extract Substances 0.000 description 3
229910000027 potassium carbonate Inorganic materials 0.000 description 3
239000000725 suspension Substances 0.000 description 3
125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 2
QQCSGYBVHXFEFG-UHFFFAOYSA-N 1-(4-bromobutyl)-4,4-dimethylpiperidine-2,6-dione Chemical compound CC1(C)CC(=O)N(CCCCBr)C(=O)C1 QQCSGYBVHXFEFG-UHFFFAOYSA-N 0.000 description 2
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
241000700159 Rattus Species 0.000 description 2
206010041349 Somnolence Diseases 0.000 description 2
125000004429 atom Chemical group 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
208000035475 disorder Diseases 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
PQLFROTZSIMBKR-UHFFFAOYSA-N ethenyl carbonochloridate Chemical compound ClC(=O)OC=C PQLFROTZSIMBKR-UHFFFAOYSA-N 0.000 description 2
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
239000012280 lithium aluminium hydride Substances 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
235000015320 potassium carbonate Nutrition 0.000 description 2
239000011734 sodium Substances 0.000 description 2
238000002560 therapeutic procedure Methods 0.000 description 2
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
WXYYGUWIYPNZNA-UHFFFAOYSA-N 1-[4-[4-(4-tert-butyl-1,3-thiazol-2-yl)piperidin-1-yl]butyl]-4,4-dimethylpiperidine-2,6-dione Chemical compound CC(C)(C)C1=CSC(C2CCN(CCCCN3C(CC(C)(C)CC3=O)=O)CC2)=N1 WXYYGUWIYPNZNA-UHFFFAOYSA-N 0.000 description 1
RNGCFTQLIWTDDK-UHFFFAOYSA-N 1-benzyl-4-(4-tert-butyl-1,3-thiazol-2-yl)piperidin-4-ol Chemical compound CC(C)(C)C1=CSC(C2(O)CCN(CC=3C=CC=CC=3)CC2)=N1 RNGCFTQLIWTDDK-UHFFFAOYSA-N 0.000 description 1
CAQXHNGYWKGBJY-UHFFFAOYSA-N 2-(1-benzylpiperidin-4-yl)-4-tert-butyl-1,3-thiazole Chemical compound CC(C)(C)C1=CSC(C2CCN(CC=3C=CC=CC=3)CC2)=N1 CAQXHNGYWKGBJY-UHFFFAOYSA-N 0.000 description 1
FWWOWPGPERBCNJ-UHFFFAOYSA-N 2-hydroxy-4-(2-hydroxyethoxy)-4-oxobutanoic acid Chemical compound OCCOC(=O)CC(O)C(O)=O FWWOWPGPERBCNJ-UHFFFAOYSA-N 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
ONZQYZKCUHFORE-UHFFFAOYSA-N 3-bromo-1,1,1-trifluoropropan-2-one Chemical compound FC(F)(F)C(=O)CBr ONZQYZKCUHFORE-UHFFFAOYSA-N 0.000 description 1
YUJCWMGBRDBPDL-UHFFFAOYSA-N 4,4-dimethylpiperidine-2,6-dione Chemical compound CC1(C)CC(=O)NC(=O)C1 YUJCWMGBRDBPDL-UHFFFAOYSA-N 0.000 description 1
QFACSDPLAUCZBD-UHFFFAOYSA-N 4-methylpiperazine-1-carbothioamide Chemical compound CN1CCN(C(N)=S)CC1 QFACSDPLAUCZBD-UHFFFAOYSA-N 0.000 description 1
SUNTXCWGIPASMO-UHFFFAOYSA-N 4-tert-butyl-2-(1,2,3,6-tetrahydropyridin-4-yl)-1,3-thiazole Chemical compound CC(C)(C)C1=CSC(C=2CCNCC=2)=N1 SUNTXCWGIPASMO-UHFFFAOYSA-N 0.000 description 1
VYJJKGZPXKEFHF-UHFFFAOYSA-N 4-tert-butyl-2-piperazin-1-yl-1,3-thiazole Chemical compound CC(C)(C)C1=CSC(N2CCNCC2)=N1 VYJJKGZPXKEFHF-UHFFFAOYSA-N 0.000 description 1
JQYOZZMLTAZELM-UHFFFAOYSA-N 4-tert-butyl-2-piperidin-4-yl-1,3-thiazole Chemical compound CC(C)(C)C1=CSC(C2CCNCC2)=N1 JQYOZZMLTAZELM-UHFFFAOYSA-N 0.000 description 1
208000019901 Anxiety disease Diseases 0.000 description 1
RENMDAKOXSCIGH-UHFFFAOYSA-N Chloroacetonitrile Chemical compound ClCC#N RENMDAKOXSCIGH-UHFFFAOYSA-N 0.000 description 1
208000020401 Depressive disease Diseases 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
239000007832 Na2SO4 Substances 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
206010041243 Social avoidant behaviour Diseases 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
230000001154 acute effect Effects 0.000 description 1
230000016571 aggressive behavior Effects 0.000 description 1
238000013019 agitation Methods 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
IMUDHTPIFIBORV-UHFFFAOYSA-N aminoethylpiperazine Chemical compound NCCN1CCNCC1 IMUDHTPIFIBORV-UHFFFAOYSA-N 0.000 description 1
230000036506 anxiety Effects 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
229910052786 argon Inorganic materials 0.000 description 1
239000002585 base 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
230000015572 biosynthetic process Effects 0.000 description 1
239000002775 capsule Substances 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
230000001684 chronic effect Effects 0.000 description 1
GVPFVAHMJGGAJG-UHFFFAOYSA-L cobalt dichloride Chemical compound [Cl-].[Cl-].[Co+2] GVPFVAHMJGGAJG-UHFFFAOYSA-L 0.000 description 1
229940097267 cobaltous chloride Drugs 0.000 description 1
238000001816 cooling Methods 0.000 description 1
ATDGTVJJHBUTRL-UHFFFAOYSA-N cyanogen bromide Chemical compound BrC#N ATDGTVJJHBUTRL-UHFFFAOYSA-N 0.000 description 1
125000001316 cycloalkyl alkyl group Chemical group 0.000 description 1
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 description 1
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
230000020335 dealkylation Effects 0.000 description 1
238000006900 dealkylation reaction Methods 0.000 description 1
238000006264 debenzylation reaction Methods 0.000 description 1
239000012259 ether extract Substances 0.000 description 1
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 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
230000000144 pharmacologic effect Effects 0.000 description 1
229920000137 polyphosphoric acid Polymers 0.000 description 1
235000011181 potassium carbonates Nutrition 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
239000002516 radical scavenger Substances 0.000 description 1
230000036385 rapid eye movement (rem) sleep Effects 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
230000009467 reduction Effects 0.000 description 1
238000010992 reflux Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
201000000980 schizophrenia Diseases 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
230000007958 sleep Effects 0.000 description 1
230000011273 social behavior Effects 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
230000008925 spontaneous activity Effects 0.000 description 1
239000012730 sustained-release form Substances 0.000 description 1
229910052723 transition metal Inorganic materials 0.000 description 1
125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
229920001567 vinyl ester resin Polymers 0.000 description 1

Classifications

- 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
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/38—Nitrogen atoms
- C07D277/42—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
- 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
- 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
- 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
- C07D513/02—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 two hetero rings
- C07D513/04—Ortho-condensed systems

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Hydrogenated Pyridines (AREA)
Thiazole And Isothizaole Compounds (AREA)

LU86487A 1985-06-22 1986-06-20 Nouveaux derives du thiazole,leur preparation et leur utilisation en therapeutique LU86487A1 (fr)

Applications Claiming Priority (8)

Application Number	Priority Date	Filing Date	Title
DE3522351		1985-06-22
DE3522354		1985-06-22
DE3522354		1985-06-22
DE3522353		1985-06-22
DE3522353		1985-06-22
DE3522351		1985-06-22
DE3605868		1986-02-24
DE3605868		1986-02-24

Publications (1)

Publication Number	Publication Date
LU86487A1 true LU86487A1 (fr)	1987-01-13

Family

ID=27433378

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
LU86487A LU86487A1 (fr)	1985-06-22	1986-06-20	Nouveaux derives du thiazole,leur preparation et leur utilisation en therapeutique

Country Status (17)

Country	Link
US (2)	US4737500A (el)
AU (1)	AU5894086A (el)
BE (1)	BE904945A (el)
CH (1)	CH668426A5 (el)
DK (1)	DK292986A (el)
ES (2)	ES8802154A1 (el)
FI (1)	FI862644A (el)
FR (1)	FR2587342A1 (el)
GB (1)	GB2177395B (el)
GR (1)	GR861601B (el)
HU (1)	HUT43600A (el)
IL (1)	IL79178A0 (el)
IT (1)	IT1203806B (el)
LU (1)	LU86487A1 (el)
NL (1)	NL8601494A (el)
PH (1)	PH23389A (el)
SE (1)	SE8602723L (el)

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US4935424A (en) *	1988-05-27	1990-06-19	Warner-Lambert Company	4 or 5-(substituted piperazinylalkyl)-2-aminothiazoles as antipsychotic agents
US5015740A (en) *	1988-08-05	1991-05-14	Janssen Pharmaceutica N.V.	Antipsychotic 3-piperazinylbenzazole derivatives
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HUT61760A (en) *	1988-09-16	1993-03-01	Pfizer	Process for producing bridged, bicyclic imides comprising 4-/4-(3-benzisothiazolyl)-1-piperazinyl/-butyl group and pharmaceutical compositions comprising such compounds
US4954503A (en) *	1989-09-11	1990-09-04	Hoechst-Roussel Pharmaceuticals, Inc.	3-(1-substituted-4-piperazinyl)-1H-indazoles
US5130315A (en) *	1991-01-10	1992-07-14	Raymond R. Wittekind	1-piperazinyl-2-butenes and -2-butynes
US5194436A (en) *	1991-01-10	1993-03-16	Hoechst-Roussel Pharmaceuticals Inc.	1-piperazinyl-2-butenes and -2-butynes
IT1251144B (it) *	1991-07-30	1995-05-04	Boehringer Ingelheim Italia	Derivati del benzimidazolone
WO1995013814A1 (en)	1993-11-19	1995-05-26	Janssen Pharmaceutica N.V.	Microencapsulated 3-piperidinyl-substituted 1,2-benzisoxazoles and 1,2-benzisothiazoles
US5889010A (en) *	1995-05-18	1999-03-30	Pfizer Inc.	Benzimidazole derivatives having dopaminergic activity
DE19746612A1 (de)	1997-10-22	1999-04-29	Basf Ag	2-Substituierte 1,2-Benzisothiazol-Derivate, ihre Herstellung und Verwendung
US7183410B2 (en) *	2001-08-02	2007-02-27	Bidachem S.P.A.	Stable polymorph of flibanserin
US20030060475A1 (en) *	2001-08-10	2003-03-27	Boehringer Ingelheim Pharma Kg	Method of using flibanserin for neuroprotection
UA78974C2 (en)	2001-10-20	2007-05-10	Boehringer Ingelheim Pharma	Use of flibanserin for treating disorders of sexual desire
US10675280B2 (en)	2001-10-20	2020-06-09	Sprout Pharmaceuticals, Inc.	Treating sexual desire disorders with flibanserin
RU2445095C2 (ru) *	2004-04-22	2012-03-20	Бёрингер Ингельхайм Интернациональ Гмбх	Новые фармацевтические композиции для лечения сексуальных расстройств
US20050239798A1 (en) *	2004-04-22	2005-10-27	Boehringer Ingelheim Pharmaceuticals, Inc.	Method for the treatment of premenstrual and other female sexual disorders
US20060025420A1 (en) *	2004-07-30	2006-02-02	Boehringer Ingelheimn International GmbH	Pharmaceutical compositions for the treatment of female sexual disorders
CA2576812A1 (en) *	2004-09-03	2006-03-09	Boehringer Ingelheim International Gmbh	Method for the treatment of attention deficit hyperactivity disorder
EP1858516A1 (en) *	2005-03-04	2007-11-28	Boehringer Ingelheim International GmbH	Pharmaceutical compositions for the treatment and/or prevention of depression
WO2006096439A2 (en) *	2005-03-04	2006-09-14	Boehringer Ingelheim International Gmbh	Pharmaceutical compositions for the treatment and/or prevention of schizophrenia and related diseases
US20060199805A1 (en) *	2005-03-04	2006-09-07	Boehringer Ingelheim International Gmbh	Pharmaceutical compositions for the treatment and/or prevention of anxiety disorders
EP1904182A2 (en) *	2005-05-06	2008-04-02	Boehringer Ingelheim International GmbH	Method for the treatment of drug abuse with flibanserin
EP1888071A1 (en) *	2005-05-19	2008-02-20	Boehringer Ingelheim International GmbH	Method for the treatment of drug-induced sexual dysfunction
US8227476B2 (en)	2005-08-03	2012-07-24	Sprout Pharmaceuticals, Inc.	Use of flibanserin in the treatment of obesity
US7923449B2 (en)	2005-10-29	2011-04-12	Boehringer Ingelheim International Gmbh	Benzimidazolone derivatives for the treatment of premenstrual and other female sexual disorders
US20070123540A1 (en) *	2005-10-29	2007-05-31	Angelo Ceci	Sexual desire enhancing medicaments comprising benzimidazolone derivatives
US20070105869A1 (en) *	2005-11-08	2007-05-10	Stephane Pollentier	Use of flibanserin for the treatment of pre-menopausal sexual desire disorders
AU2007247094B2 (en) *	2006-05-09	2012-11-01	Sprout Pharmaceuticals, Inc.	Use of flibanserin for the treatment of post-menopausal Sexual Desire Disorders
CA2654798C (en)	2006-06-30	2015-01-13	Boehringer Ingelheim International Gmbh	Flibanserin for the treatment of urinary incontinence and related diseases
EP2043648A1 (en) *	2006-07-14	2009-04-08	Boehringer Ingelheim International GmbH	Use of flibanserin for the treatment of sexual disorders in females
CL2007002214A1 (es)	2006-08-14	2008-03-07	Boehringer Ingelheim Int	Composicion farmaceutica en la forma de comprimido, donde al menos la longitud del comprimido en el estado anterior de la aplicacion es al menos 7/12 del diametro pilorico del paciente y despues de ingerirlo en estado alimentado, la longitud del comp
AU2007286288A1 (en)	2006-08-14	2008-02-21	Boehringer Ingelheim International Gmbh	Formulations of flibanserin and method for manufacturing the same
WO2008022932A2 (en)	2006-08-25	2008-02-28	Boehringer Ingelheim International Gmbh	Controlled release system and method for manufacturing the same
CA2686525C (en) *	2007-03-29	2012-05-29	Obschestvo S Ogranishennoi Otvetstvennostu "Farmving"	An antihistamine antiallergic agent and a method of deriving it
UY31335A1 (es)	2007-09-12	2009-04-30		Tratamiento de sintomas vasomotores
CA2686480A1 (en)	2008-12-15	2010-06-15	Boehringer Ingelheim International Gmbh	New salts

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BE637271A (el) *	1963-04-04	1900-01-01
DE1595923A1 (de) *	1965-02-20	1969-11-27	Merck Ag E	1-Aralkyl-4-(thiazolyl-2)-piperazine und Verfahren zu ihrer Herstellung
BE759371A (fr) *	1969-11-24	1971-05-24	Bristol Myers Co	Azaspirodecanediones heterocycliques et procedes pour leur preparation
JPS5246935B1 (el) *	1971-04-06	1977-11-29
BE787059A (fr) *	1971-08-03	1973-02-01	Wander Ag Dr A	Nouveaux derives du thiazole, leur preparation et leur application comme medicaments
CH583232A5 (el) *	1973-02-02	1976-12-31	Wander Ag Dr A
US4182763A (en) *	1978-05-22	1980-01-08	Mead Johnson & Company	Buspirone anti-anxiety method
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HUT43600A (en) *	1985-06-22	1987-11-30	Sandoz Ag	Process for production of new thiazole derivatives and medical compound containing those

1986
- 1986-06-09 HU HU862433A patent/HUT43600A/hu unknown
- 1986-06-09 NL NL8601494A patent/NL8601494A/nl not_active Application Discontinuation
- 1986-06-12 CH CH2373/86A patent/CH668426A5/de not_active IP Right Cessation
- 1986-06-18 SE SE8602723A patent/SE8602723L/xx not_active Application Discontinuation
- 1986-06-18 BE BE1/011508A patent/BE904945A/fr not_active IP Right Cessation
- 1986-06-18 FR FR8608893A patent/FR2587342A1/fr active Pending
- 1986-06-19 FI FI862644A patent/FI862644A/fi not_active IP Right Cessation
- 1986-06-19 GB GB8614974A patent/GB2177395B/en not_active Expired
- 1986-06-20 LU LU86487A patent/LU86487A1/fr unknown
- 1986-06-20 DK DK292986A patent/DK292986A/da not_active Application Discontinuation
- 1986-06-20 AU AU58940/86A patent/AU5894086A/en not_active Abandoned
- 1986-06-20 IL IL79178A patent/IL79178A0/xx unknown
- 1986-06-20 IT IT48157/86A patent/IT1203806B/it active
- 1986-06-20 GR GR861601A patent/GR861601B/el unknown
- 1986-06-20 US US06/876,617 patent/US4737500A/en not_active Expired - Fee Related
- 1986-06-20 PH PH33910A patent/PH23389A/en unknown
- 1986-06-20 ES ES556363A patent/ES8802154A1/es not_active Expired
1987
- 1987-09-15 ES ES557723A patent/ES8802045A1/es not_active Expired
1988
- 1988-02-02 US US07/151,349 patent/US4892879A/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
GR861601B (en)	1986-10-20
HUT43600A (en)	1987-11-30
ES8802154A1 (es)	1988-04-01
NL8601494A (nl)	1987-01-16
ES556363A0 (es)	1988-04-01
SE8602723L (sv)	1986-12-23
AU5894086A (en)	1986-12-24
GB2177395A (en)	1987-01-21
DK292986A (da)	1986-12-23
FI862644A (fi)	1986-12-23
FR2587342A1 (fr)	1987-03-20
IT8648157A0 (it)	1986-06-20
GB8614974D0 (en)	1986-07-23
IT1203806B (it)	1989-02-23
CH668426A5 (de)	1988-12-30
GB2177395B (en)	1989-04-26
FI862644A0 (fi)	1986-06-19
ES8802045A1 (es)	1988-03-16
SE8602723D0 (sv)	1986-06-18
ES557723A0 (es)	1988-03-16
BE904945A (fr)	1986-12-18
DK292986D0 (da)	1986-06-20
US4737500A (en)	1988-04-12
IL79178A0 (en)	1986-09-30
PH23389A (en)	1989-07-26
US4892879A (en)	1990-01-09

Publication	Publication Date	Title
LU86487A1 (fr)	1987-01-13	Nouveaux derives du thiazole,leur preparation et leur utilisation en therapeutique
EP0205375B1 (fr)	1989-11-08	Amides dérivés de la quinoléine, procédés pour leur préparation et médicaments les contenant
EP0058146B1 (fr)	1984-06-27	Nouveaux acides 2-(4-(diphénylméthyl)-1-pipérazinyl)-acétiques et leurs amides, leurs procédés de préparation et compositions thérapeutiques
EP1641763B1 (fr)	2009-09-02	Derives de 4-cyanopyrazole-3-carboxamide, leur preparation et leur application comme antagonistes des recepteurs aux cannabinoides cb1
FR2501690A1 (fr)	1982-09-17	Derives heterocycliques du type 1,2,4-triazole, leur preparation et leur application pharmacologique
EP0428437A1 (fr)	1991-05-22	Dérivés du 1,2-benzisoxazole, leurs procédés de préparation et les compositions pharmaceutiques qui les contiennent
FR2796644A1 (fr)	2001-01-26	Nouveaux derives de beta-carboline, leur procede de preparation et les compositions pharmaceutiques qui les contiennent
EP0377528B1 (fr)	1993-12-08	Pipéridines, procédés de préparation et médicaments les contenant
CA2036978A1 (fr)	1991-08-28	Derives d'aminomethylpiperidine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent
EP0433149A2 (fr)	1991-06-19	Antagonistes de la sérotonine, leur préparation et les médicaments les contenant
EP0488897B1 (fr)	1994-02-02	Nouveaux dérivés de guanidine, leur procédé de préparation et les compositions pharmaceutiques qui les contiennent
FR2681325A1 (fr)	1993-03-19	Derives de l'aminomethyl-4 piperidine, leur preparation et leur application en therapeutique.
EP0031753B1 (fr)	1984-09-19	Nouveaux dérivés de la (pipéridyl-4)-2 (quinolyl-4)-1 éthanone, produits intermédiaires et procédés pour leur préparation, et leur utilisation comme médicaments
EP1828125B1 (fr)	2008-04-09	Derives d'arylpiperazine et leur utilisation comme ligands selectifs du recepteur d3 de la dopamine
US4935414A (en)	1990-06-19	New indolylpropanols, processes for their preparation and their use, and preparations containing the compounds
EP0084993B1 (fr)	1985-07-24	Nouveaux dérivés de benzodioxine, leurs procédés de préparation et les compositions pharmaceutiques les renfermant
EP1960387A1 (fr)	2008-08-27	Derives de isoquinoline et benzo[h]isoquinoline, leur preparation et leur utilisation en therapeutique en tant qu antagonistes du recepteur de l histamine h3
CA2116881A1 (fr)	1994-09-06	Composes (aryl(alkyl)carbonyl)-heterocycliques, leurs procedes de preparation et les compositions pharmaceutiques qui les contiennent
FR2631827A1 (fr)	1989-12-01	Nouveaux derives d'(hetero)aryl-5 tetrazole, leur procede de preparation et leur application en therapeutique
EP1659112B1 (fr)	2007-06-20	Dérivés d'arylpipérazine comme ligands sélectifs du récepteur D3 de la dopamine
FR3082M (el)	1965-02-26
JPH0578554B2 (el)	1993-10-29
CH662354A5 (fr)	1987-09-30	Derives de l'hydantoine, procede pour leur preparation et medicament contenant ces derives.
EP0005091B1 (fr)	1981-11-25	Nouvelles pipérazines monosubstituées, leurs procédés de préparation et les compositions pharmaceutiques les renfermant
EP0373061B1 (fr)	1994-02-16	Nouveaux dérivés de l'indole, leur procédé de préparation et les compositions pharmaceutiques qui les contiennent