NO318790B1 - Polycykliske tiazolidin-2-ylidenaminer, medikament innbefattende samme og anvendelse av samme for fremstilling av medikament - Google Patents

Polycykliske tiazolidin-2-ylidenaminer, medikament innbefattende samme og anvendelse av samme for fremstilling av medikament Download PDF

Info

Publication number: NO318790B1
Authority: NO; Norway
Prior art keywords: phenyl; compounds; alkyl; formula; methyl
Prior art date: 1998-07-17

Application number

NO20010219A

Other languages

English (en)

Norwegian (no)

Other versions

NO20010219D0 (no

NO20010219L (no

Inventor

Hans-Jochen Lang

Karl Geisen

Gerhard Jahne

Original Assignee

Aventis Pharma Gmbh

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.)

1998-07-17

Filing date

2001-01-12

Publication date

2005-05-09

2001-01-12 Application filed by Aventis Pharma Gmbh filed Critical Aventis Pharma Gmbh

2001-01-12 Publication of NO20010219D0 publication Critical patent/NO20010219D0/no

2001-03-15 Publication of NO20010219L publication Critical patent/NO20010219L/no

2005-05-09 Publication of NO318790B1 publication Critical patent/NO318790B1/no

Links

-1 Polycyclic thiazolidin-2-ylidenamines Chemical class 0.000 title claims description 31
239000003814 drug Substances 0.000 title claims description 15
238000002360 preparation method Methods 0.000 title claims description 13
229940079593 drug Drugs 0.000 title claims description 12
150000001875 compounds Chemical class 0.000 claims description 225
239000000203 mixture Substances 0.000 claims description 97
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 54
238000000034 method Methods 0.000 claims description 35
150000003839 salts Chemical class 0.000 claims description 32
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 27
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 24
229910052739 hydrogen Inorganic materials 0.000 claims description 22
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
229910052801 chlorine Inorganic materials 0.000 claims description 18
229910052731 fluorine Inorganic materials 0.000 claims description 18
238000011282 treatment Methods 0.000 claims description 12
239000003795 chemical substances by application Substances 0.000 claims description 10
125000000217 alkyl group Chemical group 0.000 claims description 9
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
238000004519 manufacturing process Methods 0.000 claims description 8
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 5
239000013543 active substance Substances 0.000 claims description 5
229910052799 carbon Inorganic materials 0.000 claims description 5
239000011737 fluorine Substances 0.000 claims description 5
125000004076 pyridyl group Chemical group 0.000 claims description 5
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 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
125000004212 difluorophenyl group Chemical group 0.000 claims description 4
229910052760 oxygen Inorganic materials 0.000 claims description 4
238000011321 prophylaxis Methods 0.000 claims description 4
208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 4
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 3
208000008589 Obesity Diseases 0.000 claims description 3
235000020824 obesity Nutrition 0.000 claims description 3
229910052717 sulfur Inorganic materials 0.000 claims description 3
125000006528 (C2-C6) alkyl group Chemical group 0.000 claims description 2
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 2
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
239000008177 pharmaceutical agent Substances 0.000 claims description 2
230000008569 process Effects 0.000 claims description 2
125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 1
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 117
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 114
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 111
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 110
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 99
239000000243 solution Substances 0.000 description 93
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 93
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 74
238000002844 melting Methods 0.000 description 69
230000008018 melting Effects 0.000 description 69
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 59
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 50
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 50
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 48
238000006243 chemical reaction Methods 0.000 description 43
239000011541 reaction mixture Substances 0.000 description 43
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 42
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 40
239000002904 solvent Substances 0.000 description 40
238000003756 stirring Methods 0.000 description 38
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 35
229960000583 acetic acid Drugs 0.000 description 33
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 32
239000002253 acid Substances 0.000 description 32
229910052794 bromium Inorganic materials 0.000 description 32
235000002639 sodium chloride Nutrition 0.000 description 31
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 30
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 27
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 27
239000012074 organic phase Substances 0.000 description 27
235000019439 ethyl acetate Nutrition 0.000 description 26
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 25
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 24
239000012362 glacial acetic acid Substances 0.000 description 24
239000002585 base Substances 0.000 description 23
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 21
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 21
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 20
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 19
239000000460 chlorine Substances 0.000 description 19
238000010992 reflux Methods 0.000 description 19
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 18
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 18
239000000725 suspension Substances 0.000 description 18
229910052943 magnesium sulfate Inorganic materials 0.000 description 17
235000019341 magnesium sulphate Nutrition 0.000 description 17
238000000746 purification Methods 0.000 description 17
239000000741 silica gel Substances 0.000 description 17
229910002027 silica gel Inorganic materials 0.000 description 17
239000002244 precipitate Substances 0.000 description 16
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 16
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 15
239000000047 product Substances 0.000 description 14
238000000354 decomposition reaction Methods 0.000 description 13
235000011121 sodium hydroxide Nutrition 0.000 description 13
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 12
239000000126 substance Substances 0.000 description 12
238000001816 cooling Methods 0.000 description 11
239000003921 oil Substances 0.000 description 11
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 10
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 10
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 10
VLCDUOXHFNUCKK-UHFFFAOYSA-N N,N'-Dimethylthiourea Chemical compound CNC(=S)NC VLCDUOXHFNUCKK-UHFFFAOYSA-N 0.000 description 10
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 10
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 10
238000009835 boiling Methods 0.000 description 10
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
235000011054 acetic acid Nutrition 0.000 description 9
125000003118 aryl group Chemical group 0.000 description 9
230000015572 biosynthetic process Effects 0.000 description 9
239000013078 crystal Substances 0.000 description 9
239000012442 inert solvent Substances 0.000 description 9
LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 9
229910000027 potassium carbonate Inorganic materials 0.000 description 9
235000011181 potassium carbonates Nutrition 0.000 description 9
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 8
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 8
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 8
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 8
229960001701 chloroform Drugs 0.000 description 8
239000011734 sodium Substances 0.000 description 8
239000007787 solid Substances 0.000 description 8
125000003107 substituted aryl group Chemical group 0.000 description 8
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical class S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
238000003786 synthesis reaction Methods 0.000 description 8
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 8
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 7
239000003054 catalyst Substances 0.000 description 7
238000002425 crystallisation Methods 0.000 description 7
230000008025 crystallization Effects 0.000 description 7
125000001072 heteroaryl group Chemical group 0.000 description 7
239000007788 liquid Substances 0.000 description 7
239000003960 organic solvent Substances 0.000 description 7
239000008194 pharmaceutical composition Substances 0.000 description 7
229910052938 sodium sulfate Inorganic materials 0.000 description 7
235000011152 sodium sulphate Nutrition 0.000 description 7
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 6
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 6
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 6
BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 6
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 6
RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 6
150000007513 acids Chemical class 0.000 description 6
239000004480 active ingredient Substances 0.000 description 6
230000001539 anorectic effect Effects 0.000 description 6
239000000010 aprotic solvent Substances 0.000 description 6
229910052796 boron Inorganic materials 0.000 description 6
DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 6
239000003153 chemical reaction reagent Substances 0.000 description 6
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 6
238000001035 drying Methods 0.000 description 6
150000002148 esters Chemical class 0.000 description 6
238000003682 fluorination reaction Methods 0.000 description 6
150000007857 hydrazones Chemical class 0.000 description 6
ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 6
150000007522 mineralic acids Chemical class 0.000 description 6
229910052763 palladium Inorganic materials 0.000 description 6
229910052708 sodium Inorganic materials 0.000 description 6
235000017557 sodium bicarbonate Nutrition 0.000 description 6
229910000030 sodium bicarbonate Inorganic materials 0.000 description 6
229910000029 sodium carbonate Inorganic materials 0.000 description 6
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 6
239000003826 tablet Substances 0.000 description 6
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 5
LXNAVEXFUKBNMK-UHFFFAOYSA-N acetic acid;palladium Chemical compound [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 5
230000002378 acidificating effect Effects 0.000 description 5
150000001298 alcohols Chemical class 0.000 description 5
150000001450 anions Chemical class 0.000 description 5
125000004432 carbon atom Chemical group C* 0.000 description 5
239000000706 filtrate Substances 0.000 description 5
238000001914 filtration Methods 0.000 description 5
239000007789 gas Substances 0.000 description 5
QNXSIUBBGPHDDE-UHFFFAOYSA-N indan-1-one Chemical compound C1=CC=C2C(=O)CCC2=C1 QNXSIUBBGPHDDE-UHFFFAOYSA-N 0.000 description 5
229910052740 iodine Inorganic materials 0.000 description 5
150000007524 organic acids Chemical class 0.000 description 5
150000007530 organic bases Chemical class 0.000 description 5
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 4
ZHHBPTRLWXEQER-UHFFFAOYSA-N 3-oxo-1,2-dihydroindene-5-sulfinic acid Chemical compound OS(=O)C1=CC=C2CCC(=O)C2=C1 ZHHBPTRLWXEQER-UHFFFAOYSA-N 0.000 description 4
KSONICAHAPRCMV-UHFFFAOYSA-N 5-bromo-2,3-dihydroinden-1-one Chemical compound BrC1=CC=C2C(=O)CCC2=C1 KSONICAHAPRCMV-UHFFFAOYSA-N 0.000 description 4
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 4
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
239000008346 aqueous phase Substances 0.000 description 4
239000007864 aqueous solution Substances 0.000 description 4
125000001246 bromo group Chemical group Br* 0.000 description 4
229950005499 carbon tetrachloride Drugs 0.000 description 4
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
230000003197 catalytic effect Effects 0.000 description 4
239000012043 crude product Substances 0.000 description 4
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
239000003480 eluent Substances 0.000 description 4
239000012458 free base Substances 0.000 description 4
150000007529 inorganic bases Chemical class 0.000 description 4
150000002576 ketones Chemical class 0.000 description 4
230000014759 maintenance of location Effects 0.000 description 4
239000000155 melt Substances 0.000 description 4
KXKVLQRXCPHEJC-UHFFFAOYSA-N methyl acetate Chemical compound COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 4
238000002156 mixing Methods 0.000 description 4
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 4
235000017550 sodium carbonate Nutrition 0.000 description 4
239000012312 sodium hydride Substances 0.000 description 4
229910000104 sodium hydride Inorganic materials 0.000 description 4
VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 4
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 4
238000012360 testing method Methods 0.000 description 4
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
CAJDYMAFIOUARK-UHFFFAOYSA-N 1-oxo-2,3-dihydroindene-5-carbonitrile Chemical compound N#CC1=CC=C2C(=O)CCC2=C1 CAJDYMAFIOUARK-UHFFFAOYSA-N 0.000 description 3
CJMRJTDKLQFHNQ-UHFFFAOYSA-N 2-bromo-1-oxo-2,3-dihydroindene-5-carbonitrile Chemical compound N#CC1=CC=C2C(=O)C(Br)CC2=C1 CJMRJTDKLQFHNQ-UHFFFAOYSA-N 0.000 description 3
BVVHGTFVYGCNTN-UHFFFAOYSA-N 2-bromo-5-(trifluoromethoxy)-2,3-dihydroinden-1-one Chemical compound FC(F)(F)OC1=CC=C2C(=O)C(Br)CC2=C1 BVVHGTFVYGCNTN-UHFFFAOYSA-N 0.000 description 3
UOUWFJPWGQGLJF-UHFFFAOYSA-N 2-bromo-5-phenyl-2,3-dihydroinden-1-one Chemical compound C=1C=C2C(=O)C(Br)CC2=CC=1C1=CC=CC=C1 UOUWFJPWGQGLJF-UHFFFAOYSA-N 0.000 description 3
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OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
239000007868 Raney catalyst Substances 0.000 description 1
229910000564 Raney nickel Inorganic materials 0.000 description 1
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
229910005965 SO 2 Inorganic materials 0.000 description 1
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
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229910021626 Tin(II) chloride Inorganic materials 0.000 description 1
229920001615 Tragacanth Polymers 0.000 description 1
RHQDFWAXVIIEBN-UHFFFAOYSA-N Trifluoroethanol Chemical compound OCC(F)(F)F RHQDFWAXVIIEBN-UHFFFAOYSA-N 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
YBGJZYCWGNYUMA-UHFFFAOYSA-M [Cl-].[P+]=O Chemical compound [Cl-].[P+]=O YBGJZYCWGNYUMA-UHFFFAOYSA-M 0.000 description 1
FYJKEHKQUPSJDH-UHFFFAOYSA-N [dimethyl-(trimethylsilylamino)silyl]methane;potassium Chemical compound [K].C[Si](C)(C)N[Si](C)(C)C FYJKEHKQUPSJDH-UHFFFAOYSA-N 0.000 description 1
YGCFIWIQZPHFLU-UHFFFAOYSA-N acesulfame Chemical compound CC1=CC(=O)NS(=O)(=O)O1 YGCFIWIQZPHFLU-UHFFFAOYSA-N 0.000 description 1
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
150000001241 acetals Chemical class 0.000 description 1
RBYGDVHOECIAFC-UHFFFAOYSA-L acetonitrile;palladium(2+);dichloride Chemical compound [Cl-].[Cl-].[Pd+2].CC#N.CC#N RBYGDVHOECIAFC-UHFFFAOYSA-L 0.000 description 1
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239000000853 adhesive Substances 0.000 description 1
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150000001340 alkali metals Chemical group 0.000 description 1
150000001447 alkali salts Chemical class 0.000 description 1
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230000002152 alkylating effect Effects 0.000 description 1
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238000005804 alkylation reaction Methods 0.000 description 1
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125000005605 benzo group Chemical group 0.000 description 1
DMSMPAJRVJJAGA-UHFFFAOYSA-N benzo[d]isothiazol-3-one Chemical compound C1=CC=C2C(=O)NSC2=C1 DMSMPAJRVJJAGA-UHFFFAOYSA-N 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
WXNOJTUTEXAZLD-UHFFFAOYSA-L benzonitrile;dichloropalladium Chemical compound Cl[Pd]Cl.N#CC1=CC=CC=C1.N#CC1=CC=CC=C1 WXNOJTUTEXAZLD-UHFFFAOYSA-L 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
230000004071 biological effect Effects 0.000 description 1
230000037396 body weight Effects 0.000 description 1
UORVGPXVDQYIDP-BJUDXGSMSA-N borane Chemical compound [10BH3] UORVGPXVDQYIDP-BJUDXGSMSA-N 0.000 description 1
229910000085 borane Inorganic materials 0.000 description 1
239000004327 boric acid Substances 0.000 description 1
IYYIVELXUANFED-UHFFFAOYSA-N bromo(trimethyl)silane Chemical compound C[Si](C)(C)Br IYYIVELXUANFED-UHFFFAOYSA-N 0.000 description 1
244000309464 bull Species 0.000 description 1
KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
DVECBJCOGJRVPX-UHFFFAOYSA-N butyryl chloride Chemical compound CCCC(Cl)=O DVECBJCOGJRVPX-UHFFFAOYSA-N 0.000 description 1
FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 1
229910000024 caesium carbonate Inorganic materials 0.000 description 1
229910001861 calcium hydroxide Inorganic materials 0.000 description 1
159000000007 calcium salts Chemical class 0.000 description 1
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
QGJOPFRUJISHPQ-NJFSPNSNSA-N carbon disulfide-14c Chemical compound S=[14C]=S QGJOPFRUJISHPQ-NJFSPNSNSA-N 0.000 description 1
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238000006555 catalytic reaction Methods 0.000 description 1
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239000007810 chemical reaction solvent Substances 0.000 description 1
238000005660 chlorination reaction Methods 0.000 description 1
150000001804 chlorine Chemical class 0.000 description 1
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ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 1
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238000010168 coupling process Methods 0.000 description 1
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125000004093 cyano group Chemical group *C#N 0.000 description 1
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230000006735 deficit Effects 0.000 description 1
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ZHXTWWCDMUWMDI-UHFFFAOYSA-N dihydroxyboron Chemical compound O[B]O ZHXTWWCDMUWMDI-UHFFFAOYSA-N 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical compound [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
238000004821 distillation Methods 0.000 description 1
239000003651 drinking water Substances 0.000 description 1
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150000002500 ions Chemical class 0.000 description 1
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239000004310 lactic acid Substances 0.000 description 1
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150000007517 lewis acids Chemical class 0.000 description 1
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230000007774 longterm Effects 0.000 description 1
239000006210 lotion Substances 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
239000006166 lysate Substances 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
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239000002207 metabolite Substances 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
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QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
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YBYIHPMCNDRQTJ-UHFFFAOYSA-N methyl 3-[3-(trifluoromethoxy)phenyl]prop-2-enoate Chemical compound COC(=O)C=CC1=CC=CC(OC(F)(F)F)=C1 YBYIHPMCNDRQTJ-UHFFFAOYSA-N 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 1
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239000008267 milk Substances 0.000 description 1
210000004080 milk Anatomy 0.000 description 1
125000000896 monocarboxylic acid group Chemical group 0.000 description 1
238000000465 moulding Methods 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
ANWSCQFYUDOLCH-UHFFFAOYSA-N n-fluoro-4-methyl-n-propylbenzenesulfonamide Chemical compound CCCN(F)S(=O)(=O)C1=CC=C(C)C=C1 ANWSCQFYUDOLCH-UHFFFAOYSA-N 0.000 description 1
PGGWSBRXMHAXEG-UHFFFAOYSA-N n-fluoro-n,4-dimethylbenzenesulfonamide Chemical compound CN(F)S(=O)(=O)C1=CC=C(C)C=C1 PGGWSBRXMHAXEG-UHFFFAOYSA-N 0.000 description 1
CJYQZTZSYREQBD-UHFFFAOYSA-N n-fluorobenzenesulfonamide Chemical compound FNS(=O)(=O)C1=CC=CC=C1 CJYQZTZSYREQBD-UHFFFAOYSA-N 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
150000002829 nitrogen Chemical group 0.000 description 1
238000013421 nuclear magnetic resonance imaging Methods 0.000 description 1
230000000269 nucleophilic effect Effects 0.000 description 1
238000010534 nucleophilic substitution reaction Methods 0.000 description 1
239000007764 o/w emulsion Substances 0.000 description 1
239000002674 ointment Substances 0.000 description 1
239000012430 organic reaction media Substances 0.000 description 1
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PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
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239000003208 petroleum Substances 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
239000012071 phase Substances 0.000 description 1
HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 1
FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
239000003495 polar organic solvent Substances 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229940068917 polyethylene glycols Drugs 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
229920000166 polytrimethylene carbonate Polymers 0.000 description 1
229940100467 polyvinyl acetate phthalate Drugs 0.000 description 1
150000003109 potassium Chemical class 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
235000011056 potassium acetate Nutrition 0.000 description 1
NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
229910000105 potassium hydride Inorganic materials 0.000 description 1
229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
229910000160 potassium phosphate Inorganic materials 0.000 description 1
235000011009 potassium phosphates Nutrition 0.000 description 1
159000000001 potassium salts Chemical class 0.000 description 1
238000003825 pressing Methods 0.000 description 1
239000000651 prodrug Substances 0.000 description 1
229940002612 prodrug Drugs 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
239000003586 protic polar solvent Substances 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
230000009467 reduction Effects 0.000 description 1
238000011160 research Methods 0.000 description 1
229960004889 salicylic acid Drugs 0.000 description 1
239000000523 sample Substances 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
210000003491 skin Anatomy 0.000 description 1
235000015424 sodium Nutrition 0.000 description 1
WRIKHQLVHPKCJU-UHFFFAOYSA-N sodium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([Na])[Si](C)(C)C WRIKHQLVHPKCJU-UHFFFAOYSA-N 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
MNWBNISUBARLIT-UHFFFAOYSA-N sodium cyanide Chemical compound [Na+].N#[C-] MNWBNISUBARLIT-UHFFFAOYSA-N 0.000 description 1
239000012453 solvate Substances 0.000 description 1
239000007921 spray Substances 0.000 description 1
235000011150 stannous chloride Nutrition 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000012258 stirred mixture Substances 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
150000003455 sulfinic acids Chemical class 0.000 description 1
150000003457 sulfones Chemical class 0.000 description 1
150000003462 sulfoxides Chemical class 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
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229960001367 tartaric acid Drugs 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
150000003548 thiazolidines Chemical class 0.000 description 1
HFRXJVQOXRXOPP-UHFFFAOYSA-N thionyl bromide Chemical compound BrS(Br)=O HFRXJVQOXRXOPP-UHFFFAOYSA-N 0.000 description 1
AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
239000012485 toluene extract Substances 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
229940116362 tragacanth Drugs 0.000 description 1
230000037317 transdermal delivery Effects 0.000 description 1
125000002827 triflate group Chemical group FC(S(=O)(=O)O*)(F)F 0.000 description 1
ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
GRGCWBWNLSTIEN-UHFFFAOYSA-N trifluoromethanesulfonyl chloride Chemical compound FC(F)(F)S(Cl)(=O)=O GRGCWBWNLSTIEN-UHFFFAOYSA-N 0.000 description 1
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
UORVGPXVDQYIDP-UHFFFAOYSA-N trihydridoboron Substances B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 1
CWMFRHBXRUITQE-UHFFFAOYSA-N trimethylsilylacetylene Chemical group C[Si](C)(C)C#C CWMFRHBXRUITQE-UHFFFAOYSA-N 0.000 description 1
230000007306 turnover Effects 0.000 description 1
238000002604 ultrasonography Methods 0.000 description 1
229940099259 vaseline Drugs 0.000 description 1
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239000007966 viscous suspension Substances 0.000 description 1
239000007762 w/o emulsion Substances 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000001993 wax Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1

Classifications

- 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
- 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
- A61P3/04—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
- 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
- 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
- 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

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Diabetes (AREA)
General Health & Medical Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Engineering & Computer Science (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
General Chemical & Material Sciences (AREA)
Hematology (AREA)
Obesity (AREA)
Emergency Medicine (AREA)
Endocrinology (AREA)
Child & Adolescent Psychology (AREA)
Plural Heterocyclic Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Thiazole And Isothizaole Compounds (AREA)

NO20010219A 1998-07-17 2001-01-12 Polycykliske tiazolidin-2-ylidenaminer, medikament innbefattende samme og anvendelse av samme for fremstilling av medikament NO318790B1 (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE19831878A DE19831878C2 (de)	1998-07-17	1998-07-17	Polycyclische Thiazolidin-2-yliden Amine, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel
PCT/EP1999/004644 WO2000004006A1 (de)	1998-07-17	1999-07-03	Polycyclische thiazolidin-2-yliden amine, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel

Publications (3)

Publication Number	Publication Date
NO20010219D0 NO20010219D0 (no)	2001-01-12
NO20010219L NO20010219L (no)	2001-03-15
NO318790B1 true NO318790B1 (no)	2005-05-09

Family

ID=7874197

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO20010219A NO318790B1 (no)	1998-07-17	2001-01-12	Polycykliske tiazolidin-2-ylidenaminer, medikament innbefattende samme og anvendelse av samme for fremstilling av medikament

Country Status (26)

Country	Link
US (1)	US6159996A (xx)
EP (1)	EP1098891B1 (xx)
JP (1)	JP3541808B2 (xx)
KR (1)	KR20010083118A (xx)
CN (1)	CN1144797C (xx)
AR (1)	AR019925A1 (xx)
AT (1)	ATE301645T1 (xx)
AU (1)	AU767151B2 (xx)
BR (1)	BR9912151A (xx)
CA (1)	CA2337838A1 (xx)
CL (1)	CL2004000219A1 (xx)
DE (2)	DE19831878C2 (xx)
DK (1)	DK1098891T3 (xx)
ES (1)	ES2246089T3 (xx)
HK (1)	HK1038560A1 (xx)
HU (1)	HUP0104942A3 (xx)
ID (1)	ID26985A (xx)
IL (1)	IL140767A (xx)
NO (1)	NO318790B1 (xx)
NZ (1)	NZ509395A (xx)
PL (1)	PL345619A1 (xx)
PT (1)	PT1098891E (xx)
RU (1)	RU2236405C2 (xx)
TR (1)	TR200100125T2 (xx)
WO (1)	WO2000004006A1 (xx)
ZA (1)	ZA200100279B (xx)

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE19908533A1 (de) *	1999-02-26	2000-08-31	Aventis Pharma Gmbh	Polycyclische Thiazol-Systeme, Verfahren zu ihrer Herstellung und Arzneimittel enthaltend diese Verbindungen
DE19908538A1 (de)	1999-02-26	2000-08-31	Aventis Pharma Gmbh	Polycyclische 2-Amino-Thiazol Systeme, Verfahren zu ihrer Herstellung und Arzneimittel enthaltend diese Verbindungen
DE19908537A1 (de) *	1999-02-26	2000-08-31	Aventis Pharma Gmbh	Verwendung von polycyclischen 2-Amino-Thiazol Systemen zur Herstellung von Medikamenten zur Prophylaxe oder Behandlung von Obesitas
IL149400A0 (en) *	1999-11-05	2002-11-10	Aventis Pharma Gmbh	Indeno-, naphtho-, and benzocyclohepta-dihydrothiazole derivatives, the production thereof and their use as anorectic medicaments
AU4413601A (en) *	2000-02-26	2001-09-03	Aventis Pharma Gmbh	8,8a-dihydro-indeno(1,2-d)thiazole derivatives with a sulphonamido or sulphono substituent in the 2 position, a method for production thereof and use thereof as a medicament
DE10142722A1 (de)	2001-08-31	2003-03-27	Aventis Pharma Deutschland GmbH, 65929 Frankfurt	C2-substituierte Indan-1-one und ihre Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel
DE10142665B4 (de) *	2001-08-31	2004-05-06	Aventis Pharma Deutschland Gmbh	C2-Disubstituierte Indan-1-one und ihre Derivate
US7977532B2 (en) *	2002-09-05	2011-07-12	The Procter & Gamble Company	Tampon with clean appearance post use
US8124582B2 (en) *	2002-12-06	2012-02-28	Fibrogen, Inc.	Treatment of diabetes
EP1767565B1 (en) *	2004-07-09	2015-04-01	Nissan Chemical Industries, Ltd.	Process for purification of oligoanilines and oligoanilines
JP2009514915A (ja) *	2005-11-08	2009-04-09	ラボラトリオス・デル・ドクトル・エステベ・ソシエダッド・アノニマ	インデン誘導体、それらの製造および薬剤としての使用
MX2010010659A (es) *	2008-03-31	2010-10-26	Genentech Inc	Compuestos de benzopirano y benzoxepina, inhibidores de fosfoinoinositida 3-cinasas y metodos para utilizarlos.
PT2686302T (pt)	2011-03-16	2016-11-02	Mitsubishi Tanabe Pharma Corp	Compostos de sulfonamida tendo atividade antagonista de trpm8

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Publication number	Priority date	Publication date	Assignee	Title
US3507868A (en) *	1968-10-21	1970-04-21	Sandoz Ag	Imidazo(2,1-b)thiazoles and thiazolo(3,2-a)pyrimidines
DE2640358A1 (de) *	1976-09-08	1978-03-16	Hoechst Ag	Thiazolidinderivate und verfahren zu ihrer herstellung

1998
- 1998-07-17 DE DE19831878A patent/DE19831878C2/de not_active Expired - Fee Related
1999
- 1999-07-03 PT PT99934568T patent/PT1098891E/pt unknown
- 1999-07-03 KR KR1020017000694A patent/KR20010083118A/ko not_active Application Discontinuation
- 1999-07-03 CA CA002337838A patent/CA2337838A1/en not_active Abandoned
- 1999-07-03 DE DE59912402T patent/DE59912402D1/de not_active Expired - Lifetime
- 1999-07-03 JP JP2000560113A patent/JP3541808B2/ja not_active Expired - Fee Related
- 1999-07-03 WO PCT/EP1999/004644 patent/WO2000004006A1/de not_active Application Discontinuation
- 1999-07-03 BR BR9912151-4A patent/BR9912151A/pt not_active Application Discontinuation
- 1999-07-03 AU AU50308/99A patent/AU767151B2/en not_active Ceased
- 1999-07-03 PL PL99345619A patent/PL345619A1/xx not_active Application Discontinuation
- 1999-07-03 NZ NZ509395A patent/NZ509395A/en unknown
- 1999-07-03 CN CNB998087165A patent/CN1144797C/zh not_active Expired - Fee Related
- 1999-07-03 ID IDW20010125A patent/ID26985A/id unknown
- 1999-07-03 IL IL14076799A patent/IL140767A/xx not_active IP Right Cessation
- 1999-07-03 HU HU0104942A patent/HUP0104942A3/hu unknown
- 1999-07-03 DK DK99934568T patent/DK1098891T3/da active
- 1999-07-03 AT AT99934568T patent/ATE301645T1/de not_active IP Right Cessation
- 1999-07-03 TR TR2001/00125T patent/TR200100125T2/xx unknown
- 1999-07-03 ES ES99934568T patent/ES2246089T3/es not_active Expired - Lifetime
- 1999-07-03 EP EP99934568A patent/EP1098891B1/de not_active Expired - Lifetime
- 1999-07-03 RU RU2001104480/04A patent/RU2236405C2/ru not_active IP Right Cessation
- 1999-07-12 US US09/351,621 patent/US6159996A/en not_active Expired - Lifetime
- 1999-07-15 AR ARP990103487A patent/AR019925A1/es unknown
2001
- 2001-01-10 ZA ZA200100279A patent/ZA200100279B/en unknown
- 2001-01-12 NO NO20010219A patent/NO318790B1/no unknown
- 2001-12-28 HK HK01109163A patent/HK1038560A1/xx not_active IP Right Cessation
2004
- 2004-02-06 CL CL200400219A patent/CL2004000219A1/es unknown

Also Published As

Publication number	Publication date
HUP0104942A2 (hu)	2002-04-29
RU2236405C2 (ru)	2004-09-20
JP2002520404A (ja)	2002-07-09
AR019925A1 (es)	2002-03-27
DE19831878A1 (de)	2000-01-27
ATE301645T1 (de)	2005-08-15
WO2000004006A1 (de)	2000-01-27
JP3541808B2 (ja)	2004-07-14
HUP0104942A3 (en)	2003-12-29
AU5030899A (en)	2000-02-07
BR9912151A (pt)	2001-04-10
CN1309653A (zh)	2001-08-22
ZA200100279B (en)	2001-08-07
US6159996A (en)	2000-12-12
HK1038560A1 (en)	2002-03-22
NZ509395A (en)	2003-10-31
NO20010219D0 (no)	2001-01-12
IL140767A (en)	2005-12-18
IL140767A0 (en)	2002-02-10
DE19831878C2 (de)	2001-05-17
ES2246089T3 (es)	2006-02-01
AU767151B2 (en)	2003-10-30
NO20010219L (no)	2001-03-15
ID26985A (id)	2001-02-22
PL345619A1 (en)	2002-01-02
PT1098891E (pt)	2005-11-30
EP1098891A1 (de)	2001-05-16
TR200100125T2 (tr)	2001-05-21
DE59912402D1 (de)	2005-09-15
CN1144797C (zh)	2004-04-07
CL2004000219A1 (es)	2005-04-22
CA2337838A1 (en)	2000-01-27
DK1098891T3 (da)	2005-12-12
EP1098891B1 (de)	2005-08-10
KR20010083118A (ko)	2001-08-31

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