DE19908533A1 - Polycyclische Thiazol-Systeme, Verfahren zu ihrer Herstellung und Arzneimittel enthaltend diese Verbindungen - Google Patents
Polycyclische Thiazol-Systeme, Verfahren zu ihrer Herstellung und Arzneimittel enthaltend diese VerbindungenInfo
- Publication number
- DE19908533A1 DE19908533A1 DE19908533A DE19908533A DE19908533A1 DE 19908533 A1 DE19908533 A1 DE 19908533A1 DE 19908533 A DE19908533 A DE 19908533A DE 19908533 A DE19908533 A DE 19908533A DE 19908533 A1 DE19908533 A1 DE 19908533A1
- Authority
- DE
- Germany
- Prior art keywords
- alkyl
- phenyl
- conh
- ocf
- hydrogen
- Prior art date
- Legal status (The legal status 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 status listed.)
- Withdrawn
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 60
- 238000000034 method Methods 0.000 title claims abstract description 9
- 239000003814 drug Substances 0.000 title claims 4
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 title abstract description 4
- 125000003367 polycyclic group Chemical group 0.000 title abstract description 4
- 238000002360 preparation method Methods 0.000 title description 7
- 150000003839 salts Chemical class 0.000 claims abstract description 19
- 230000001539 anorectic effect Effects 0.000 claims abstract description 7
- 206010061428 decreased appetite Diseases 0.000 claims abstract description 4
- 238000004519 manufacturing process Methods 0.000 claims abstract description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 94
- -1 alkynyl radicals Chemical class 0.000 claims description 34
- 229910052731 fluorine Inorganic materials 0.000 claims description 28
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 24
- 229910052794 bromium Inorganic materials 0.000 claims description 23
- 239000000203 mixture Substances 0.000 claims description 23
- 229910052801 chlorine Inorganic materials 0.000 claims description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- 239000001257 hydrogen Substances 0.000 claims description 18
- 150000002431 hydrogen Chemical class 0.000 claims description 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
- 239000004480 active ingredient Substances 0.000 claims description 12
- 239000004305 biphenyl Substances 0.000 claims description 12
- 235000010290 biphenyl Nutrition 0.000 claims description 12
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 12
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 12
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 10
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 10
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 10
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 10
- 239000011737 fluorine Substances 0.000 claims description 10
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 8
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 8
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 8
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 8
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 8
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 8
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 8
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 6
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 125000002541 furyl group Chemical group 0.000 claims description 6
- 125000000814 indol-3-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([H])=C([*])C2=C1[H] 0.000 claims description 6
- 125000004531 indol-5-yl group Chemical group [H]N1C([H])=C([H])C2=C([H])C(*)=C([H])C([H])=C12 0.000 claims description 6
- 229910052740 iodine Inorganic materials 0.000 claims description 6
- 125000001624 naphthyl group Chemical group 0.000 claims description 6
- 125000004076 pyridyl group Chemical group 0.000 claims description 6
- 125000001544 thienyl group Chemical group 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 150000005840 aryl radicals Chemical class 0.000 claims description 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 4
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 125000004190 benzothiazol-2-yl group Chemical group [H]C1=C([H])C([H])=C2N=C(*)SC2=C1[H] 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000004299 tetrazol-5-yl group Chemical group [H]N1N=NC(*)=N1 0.000 claims description 4
- 125000006555 (C3-C5) cycloalkyl group Chemical group 0.000 claims description 2
- 125000001506 1,2,3-triazol-5-yl group Chemical group [H]N1N=NC([H])=C1[*] 0.000 claims description 2
- 125000001305 1,2,4-triazol-3-yl group Chemical group [H]N1N=C([*])N=C1[H] 0.000 claims description 2
- 125000001414 1,2,4-triazol-5-yl group Chemical group [H]N1N=C([H])N=C1[*] 0.000 claims description 2
- 125000003363 1,3,5-triazinyl group Chemical group N1=C(N=CN=C1)* 0.000 claims description 2
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000004174 2-benzimidazolyl group Chemical group [H]N1C(*)=NC2=C([H])C([H])=C([H])C([H])=C12 0.000 claims description 2
- 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000001397 3-pyrrolyl group Chemical group [H]N1C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- KDDQRKBRJSGMQE-UHFFFAOYSA-N 4-thiazolyl Chemical compound [C]1=CSC=N1 KDDQRKBRJSGMQE-UHFFFAOYSA-N 0.000 claims description 2
- 125000004539 5-benzimidazolyl group Chemical group N1=CNC2=C1C=CC(=C2)* 0.000 claims description 2
- CWDWFSXUQODZGW-UHFFFAOYSA-N 5-thiazolyl Chemical group [C]1=CN=CS1 CWDWFSXUQODZGW-UHFFFAOYSA-N 0.000 claims description 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000005322 morpholin-1-yl group Chemical group 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 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 claims description 2
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims description 2
- 125000004526 pyridazin-2-yl group Chemical group N1N(C=CC=C1)* 0.000 claims description 2
- 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 claims description 2
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 2
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 2
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 2
- 125000001425 triazolyl group Chemical group 0.000 claims description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 27
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 238000002844 melting Methods 0.000 description 14
- 230000008018 melting Effects 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 239000000460 chlorine Substances 0.000 description 11
- 239000000243 solution Substances 0.000 description 10
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 239000008194 pharmaceutical composition Substances 0.000 description 8
- 229960000583 acetic acid Drugs 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000012362 glacial acetic acid Substances 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- 239000003826 tablet Substances 0.000 description 5
- XNTGHLJYUJLXQE-UHFFFAOYSA-N 2-bromo-5-chloro-2,3-dihydroinden-1-one Chemical compound ClC1=CC=C2C(=O)C(Br)CC2=C1 XNTGHLJYUJLXQE-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- YUKQRDCYNOVPGJ-UHFFFAOYSA-N thioacetamide Chemical compound CC(N)=S YUKQRDCYNOVPGJ-UHFFFAOYSA-N 0.000 description 4
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- 238000011282 treatment Methods 0.000 description 4
- VIEVHKWLWQKNBZ-UHFFFAOYSA-N 2-bromo-5-(3-chlorophenyl)-2,3-dihydroinden-1-one Chemical compound ClC1=CC=CC(C=2C=C3CC(Br)C(=O)C3=CC=2)=C1 VIEVHKWLWQKNBZ-UHFFFAOYSA-N 0.000 description 3
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 3
- YIDGIARJGMSRNL-UHFFFAOYSA-N 6-(3-chlorophenyl)-2-methyl-4h-indeno[1,2-d][1,3]thiazole Chemical compound S1C(C)=NC(C2=CC=3)=C1CC2=CC=3C1=CC=CC(Cl)=C1 YIDGIARJGMSRNL-UHFFFAOYSA-N 0.000 description 3
- MSBHYIHKYKSVAP-UHFFFAOYSA-N 6-chloro-2-methyl-4h-indeno[1,2-d][1,3]thiazole;hydrochloride Chemical compound Cl.ClC1=CC=C2C(N=C(S3)C)=C3CC2=C1 MSBHYIHKYKSVAP-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 230000002349 favourable effect Effects 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 3
- 239000007937 lozenge Substances 0.000 description 3
- 235000013336 milk Nutrition 0.000 description 3
- 239000008267 milk Substances 0.000 description 3
- 210000004080 milk Anatomy 0.000 description 3
- 150000007522 mineralic acids Chemical class 0.000 description 3
- 150000007524 organic acids Chemical class 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000000651 prodrug Substances 0.000 description 3
- 229940002612 prodrug Drugs 0.000 description 3
- 238000011321 prophylaxis Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
- CZTIMLZELSQIHQ-UHFFFAOYSA-N 2-(6-chloro-4h-indeno[1,2-d][1,3]thiazol-2-yl)acetonitrile Chemical compound ClC1=CC=C2C(N=C(CC#N)S3)=C3CC2=C1 CZTIMLZELSQIHQ-UHFFFAOYSA-N 0.000 description 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 2
- GTZDCUBDOYTXOV-UHFFFAOYSA-N 2-bromo-5-(2,2,2-trifluoroethoxy)-2,3-dihydroinden-1-one Chemical compound FC(F)(F)COC1=CC=C2C(=O)C(Br)CC2=C1 GTZDCUBDOYTXOV-UHFFFAOYSA-N 0.000 description 2
- JURPKOMLNONAIH-UHFFFAOYSA-N 2-methyl-6-(2,2,2-trifluoroethoxy)-2h-indeno[1,2-d][1,3]thiazole;hydrobromide Chemical compound Br.FC(F)(F)COC1=CC=C2C3=NC(C)SC3=CC2=C1 JURPKOMLNONAIH-UHFFFAOYSA-N 0.000 description 2
- JYHZQBSBJFHAII-UHFFFAOYSA-N 5-(2,2,2-trifluoroethoxy)-2,3-dihydroinden-1-one Chemical compound FC(F)(F)COC1=CC=C2C(=O)CCC2=C1 JYHZQBSBJFHAII-UHFFFAOYSA-N 0.000 description 2
- DTDKQCJBZOQMKY-UHFFFAOYSA-N 6-chloro-2-methyl-3a,4-dihydroindeno[1,2-d][1,3]thiazol-8b-ol Chemical compound ClC1=CC=C2C3(O)N=C(C)SC3CC2=C1 DTDKQCJBZOQMKY-UHFFFAOYSA-N 0.000 description 2
- SEPKBICUAPMRII-UHFFFAOYSA-N 6-chloro-2-methyl-4h-indeno[1,2-d][1,3]thiazole Chemical compound ClC1=CC=C2C(N=C(S3)C)=C3CC2=C1 SEPKBICUAPMRII-UHFFFAOYSA-N 0.000 description 2
- WEIREUNFIXNUSL-UHFFFAOYSA-N 8-bromo-2-phenyl-4,5-dihydrobenzo[e][1,3]benzothiazole Chemical compound N=1C=2C3=CC(Br)=CC=C3CCC=2SC=1C1=CC=CC=C1 WEIREUNFIXNUSL-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 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 2
- 229930006000 Sucrose Natural products 0.000 description 2
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric Acid Chemical compound [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 235000011054 acetic acid Nutrition 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000001345 alkine derivatives Chemical class 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- 239000002830 appetite depressant Substances 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 235000020186 condensed milk Nutrition 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000001419 dependent effect Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 229940093915 gynecological organic acid Drugs 0.000 description 2
- QNXSIUBBGPHDDE-UHFFFAOYSA-N indan-1-one Chemical class C1=CC=C2C(=O)CCC2=C1 QNXSIUBBGPHDDE-UHFFFAOYSA-N 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/84—Naphthothiazoles
-
- 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
- C07D417/04—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 directly linked by a ring-member-to-ring-member bond
-
- 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
- C07D417/06—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 carbon chain containing only aliphatic carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Diabetes (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Child & Adolescent Psychology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Plural Heterocyclic Compounds (AREA)
Priority Applications (21)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19908533A DE19908533A1 (de) | 1999-02-26 | 1999-02-26 | Polycyclische Thiazol-Systeme, Verfahren zu ihrer Herstellung und Arzneimittel enthaltend diese Verbindungen |
| DK00902658T DK1183247T3 (da) | 1999-02-26 | 2000-02-05 | Polycycliske thiazolsystemer, fremgangsmåde til fremstilling heraf og lægemidler indeholdende disse forbindelser |
| JP2000602224A JP4728485B2 (ja) | 1999-02-26 | 2000-02-05 | 多環式チアゾール系および食欲抑制剤としてのその使用 |
| CNB008042365A CN1149205C (zh) | 1999-02-26 | 2000-02-05 | 多环的噻唑体系和它们作为减食欲剂的用途 |
| AU24416/00A AU762802B2 (en) | 1999-02-26 | 2000-02-05 | Polycyclic thiazole systems and their utilization as anorectics |
| KR1020017010874A KR20020000545A (ko) | 1999-02-26 | 2000-02-05 | 폴리사이클릭 티아졸계 및 식욕 억제제로서의 이의 용도 |
| PT00902658T PT1183247E (pt) | 1999-02-26 | 2000-02-05 | Sistemas tiazole policiclicos e sua utilizacao como anorecticos |
| PCT/EP2000/000927 WO2000051997A1 (de) | 1999-02-26 | 2000-02-05 | Polycyclische thiazol-systeme und ihre verwendung als anorektika |
| HK02104057.0A HK1042300B (zh) | 1999-02-26 | 2000-02-05 | 多環的噻唑體系和它們作為減食慾劑的用途 |
| DE50010403T DE50010403D1 (de) | 1999-02-26 | 2000-02-05 | Polycyclische thiazol-systeme und ihre verwendung als anorektika |
| AT00902658T ATE296295T1 (de) | 1999-02-26 | 2000-02-05 | Polycyclische thiazol-systeme und ihre verwendung als anorektika |
| EP00902658A EP1183247B1 (de) | 1999-02-26 | 2000-02-05 | Polycyclische thiazol-systeme und ihre verwendung als anorektika |
| BR0008511-1A BR0008511A (pt) | 1999-02-26 | 2000-02-05 | Sistemas tiazol policìclicos e seu emprego como anoréticos contendo estes compostos |
| ES00902658T ES2241574T3 (es) | 1999-02-26 | 2000-02-05 | Sistemas policiclicos de tiazol y su uso como anorexicos. |
| CA002364903A CA2364903A1 (en) | 1999-02-26 | 2000-02-05 | Polycyclic thiazole systems and their utilization as anorectics |
| US09/501,210 US6187801B1 (en) | 1999-02-26 | 2000-02-10 | Polycyclic thiazole systems, processes for their preparation and pharmaceuticals comprising these compounds |
| CO00011822A CO5180595A1 (es) | 1999-02-26 | 2000-02-21 | Sistemas policiclicos de tiazol, procedimiento para su preparacion y medicamento que contiene a estos compuestos |
| ARP000100787 AR022736A1 (es) | 1999-02-26 | 2000-02-24 | Sistemas policiclicos de tiazol, medicamento que contiene a estos compuestos, y procedimiento para la preparacion del medicamento |
| MYPI20000739A MY133195A (en) | 1999-02-26 | 2000-02-25 | Polycyclic thiazole systems, processes for their preparation and pharmaceuticals comprising these compounds |
| TW089103194A TW593294B (en) | 1999-02-26 | 2000-03-20 | Polycyclic thiazole systems having anorectic activity, processes for their preparation and pharmaceutical composition comprising these compounds |
| ZA200106440A ZA200106440B (en) | 1999-02-26 | 2001-08-08 | Polycyclic thiazole systems and their utilization as anorectics. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19908533A DE19908533A1 (de) | 1999-02-26 | 1999-02-26 | Polycyclische Thiazol-Systeme, Verfahren zu ihrer Herstellung und Arzneimittel enthaltend diese Verbindungen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE19908533A1 true DE19908533A1 (de) | 2000-08-31 |
Family
ID=7899078
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19908533A Withdrawn DE19908533A1 (de) | 1999-02-26 | 1999-02-26 | Polycyclische Thiazol-Systeme, Verfahren zu ihrer Herstellung und Arzneimittel enthaltend diese Verbindungen |
| DE50010403T Expired - Lifetime DE50010403D1 (de) | 1999-02-26 | 2000-02-05 | Polycyclische thiazol-systeme und ihre verwendung als anorektika |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE50010403T Expired - Lifetime DE50010403D1 (de) | 1999-02-26 | 2000-02-05 | Polycyclische thiazol-systeme und ihre verwendung als anorektika |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US6187801B1 (https=) |
| EP (1) | EP1183247B1 (https=) |
| JP (1) | JP4728485B2 (https=) |
| KR (1) | KR20020000545A (https=) |
| CN (1) | CN1149205C (https=) |
| AT (1) | ATE296295T1 (https=) |
| AU (1) | AU762802B2 (https=) |
| BR (1) | BR0008511A (https=) |
| CA (1) | CA2364903A1 (https=) |
| CO (1) | CO5180595A1 (https=) |
| DE (2) | DE19908533A1 (https=) |
| DK (1) | DK1183247T3 (https=) |
| ES (1) | ES2241574T3 (https=) |
| HK (1) | HK1042300B (https=) |
| MY (1) | MY133195A (https=) |
| PT (1) | PT1183247E (https=) |
| TW (1) | TW593294B (https=) |
| WO (1) | WO2000051997A1 (https=) |
| ZA (1) | ZA200106440B (https=) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2000051579A3 (de) * | 1999-02-26 | 2001-01-11 | Aventis Pharma Gmbh | Verwendung von polycyclischen thiazol-systemen zur herstellung von medikamenten zur prophylaxe oder behandlung von obesitas |
| WO2003020695A1 (de) * | 2001-08-31 | 2003-03-13 | Aventis Pharma Deutschland Gmbh | C2-disubstituierte indan-1-ol-systeme, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100763214B1 (ko) * | 2000-02-26 | 2007-10-08 | 사노피-아벤티스 도이칠란트 게엠베하 | 2 위치에서 설폰아미도 또는 설포노 치환체를 갖는 8,8ａ-디하이드로-인데노[1,2-ｄ]티아졸 유도체, 이의 제조방법 및 이를 포함하는 약제 |
| KR100712171B1 (ko) * | 2004-09-17 | 2007-05-02 | 김진우 | 폐타이어를 이용한 조립식 배관블록 |
| ES2480994T3 (es) | 2008-03-31 | 2014-07-29 | Genentech, Inc. | Compuestos de tipo benzopirano y benzoxepina inhibidores de PI3K y métodos de uso |
| ES2558742T3 (es) | 2009-09-28 | 2016-02-08 | F. Hoffmann-La Roche Ag | Compuestos inhibidores de PI3K de benzoxepina y métodos de uso |
| ES2570569T3 (es) | 2009-09-28 | 2016-05-19 | Hoffmann La Roche | Compuestos de benzoxazepina como inhibidores de la PI3K y métodos de uso |
| WO2012126901A1 (en) | 2011-03-21 | 2012-09-27 | F. Hoffmann-La Roche Ag | Benzoxazepin compounds selective for pi3k p110 delta and methods of use |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2640358A1 (de) * | 1976-09-08 | 1978-03-16 | Hoechst Ag | Thiazolidinderivate und verfahren zu ihrer herstellung |
| NZ281718A (en) * | 1994-03-11 | 1997-08-22 | Yamanouchi Pharma Co Ltd | Heterocyclically-substituted (condensed) thiazoles |
| JPH1179993A (ja) * | 1997-09-05 | 1999-03-23 | Sumitomo Pharmaceut Co Ltd | 免疫抑制剤 |
| DE19831878C2 (de) * | 1998-07-17 | 2001-05-17 | Aventis Pharma Gmbh | Polycyclische Thiazolidin-2-yliden Amine, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
| DE19908535A1 (de) * | 1999-02-26 | 2000-08-31 | Aventis Pharma Gmbh | Verwendung von polycyclischen Thiazol-Systemen zur Herstellung von Medikamenten zur Prophylaxe oder Behandlung von Obesitas |
-
1999
- 1999-02-26 DE DE19908533A patent/DE19908533A1/de not_active Withdrawn
-
2000
- 2000-02-05 PT PT00902658T patent/PT1183247E/pt unknown
- 2000-02-05 WO PCT/EP2000/000927 patent/WO2000051997A1/de not_active Ceased
- 2000-02-05 KR KR1020017010874A patent/KR20020000545A/ko not_active Ceased
- 2000-02-05 DE DE50010403T patent/DE50010403D1/de not_active Expired - Lifetime
- 2000-02-05 ES ES00902658T patent/ES2241574T3/es not_active Expired - Lifetime
- 2000-02-05 AT AT00902658T patent/ATE296295T1/de not_active IP Right Cessation
- 2000-02-05 CN CNB008042365A patent/CN1149205C/zh not_active Expired - Fee Related
- 2000-02-05 HK HK02104057.0A patent/HK1042300B/zh not_active IP Right Cessation
- 2000-02-05 JP JP2000602224A patent/JP4728485B2/ja not_active Expired - Fee Related
- 2000-02-05 EP EP00902658A patent/EP1183247B1/de not_active Expired - Lifetime
- 2000-02-05 BR BR0008511-1A patent/BR0008511A/pt not_active IP Right Cessation
- 2000-02-05 AU AU24416/00A patent/AU762802B2/en not_active Ceased
- 2000-02-05 CA CA002364903A patent/CA2364903A1/en not_active Abandoned
- 2000-02-05 DK DK00902658T patent/DK1183247T3/da active
- 2000-02-10 US US09/501,210 patent/US6187801B1/en not_active Expired - Lifetime
- 2000-02-21 CO CO00011822A patent/CO5180595A1/es not_active Application Discontinuation
- 2000-02-25 MY MYPI20000739A patent/MY133195A/en unknown
- 2000-03-20 TW TW089103194A patent/TW593294B/zh not_active IP Right Cessation
-
2001
- 2001-08-08 ZA ZA200106440A patent/ZA200106440B/en unknown
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2000051579A3 (de) * | 1999-02-26 | 2001-01-11 | Aventis Pharma Gmbh | Verwendung von polycyclischen thiazol-systemen zur herstellung von medikamenten zur prophylaxe oder behandlung von obesitas |
| US6329407B1 (en) | 1999-02-26 | 2001-12-11 | Aventispharma Deutschland Gmbh | Use of polycyclic thiazole systems for the treatment of obesity |
| WO2003020695A1 (de) * | 2001-08-31 | 2003-03-13 | Aventis Pharma Deutschland Gmbh | C2-disubstituierte indan-1-ol-systeme, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel |
| US6982353B2 (en) | 2001-08-31 | 2006-01-03 | Aventis Pharma Deutschland Gmbh | C2-disubstituted indan-1-ol compounds, their derivatives, processes for their preparation, and their use as pharmaceuticals |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2002538150A (ja) | 2002-11-12 |
| BR0008511A (pt) | 2002-04-02 |
| EP1183247B1 (de) | 2005-05-25 |
| DE50010403D1 (de) | 2005-06-30 |
| AU2441600A (en) | 2000-09-21 |
| ES2241574T3 (es) | 2005-11-01 |
| HK1042300A1 (en) | 2002-08-09 |
| KR20020000545A (ko) | 2002-01-05 |
| CA2364903A1 (en) | 2000-09-08 |
| CN1341108A (zh) | 2002-03-20 |
| PT1183247E (pt) | 2005-07-29 |
| AU762802B2 (en) | 2003-07-03 |
| MY133195A (en) | 2007-10-31 |
| ATE296295T1 (de) | 2005-06-15 |
| JP4728485B2 (ja) | 2011-07-20 |
| ZA200106440B (en) | 2002-03-06 |
| WO2000051997A1 (de) | 2000-09-08 |
| TW593294B (en) | 2004-06-21 |
| DK1183247T3 (da) | 2005-09-19 |
| HK1042300B (zh) | 2004-12-10 |
| CN1149205C (zh) | 2004-05-12 |
| CO5180595A1 (es) | 2002-07-30 |
| EP1183247A1 (de) | 2002-03-06 |
| US6187801B1 (en) | 2001-02-13 |
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Legal Events
| Date | Code | Title | Description |
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| 8127 | New person/name/address of the applicant |
Owner name: SANOFI-AVENTIS DEUTSCHLAND GMBH, 65929 FRANKFURT, |
|
| 8130 | Withdrawal |