UA82872C2 - Benzo [1,2,5] thiadiazole compounds - Google Patents

Benzo [1,2,5] thiadiazole compounds Download PDF

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Publication number: UA82872C2
Authority: UA; Ukraine
Prior art keywords: phenyl; width; alkyl; carbon; benzo
Prior art date: 2003-03-28

Application number

UAA200509353A

Other languages

English (en)

Ukrainian (uk)

Original Assignee

Janssen Pharmaceutica Nv

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.)

2003-03-28

Filing date

2004-03-26

Publication date

2008-05-26

2004-03-26 Application filed by Janssen Pharmaceutica Nv filed Critical Janssen Pharmaceutica Nv

2008-05-26 Publication of UA82872C2 publication Critical patent/UA82872C2/uk

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PDQRQJVPEFGVRK-UHFFFAOYSA-N 2,1,3-benzothiadiazole Chemical class C1=CC=CC2=NSN=C21 PDQRQJVPEFGVRK-UHFFFAOYSA-N 0.000 title 1
230000001404 mediated effect Effects 0.000 claims abstract description 6
150000001875 compounds Chemical class 0.000 claims description 263
-1 hydroxyC.i.dalalkyl Chemical group 0.000 claims description 250
238000000034 method Methods 0.000 claims description 123
229910052799 carbon Inorganic materials 0.000 claims description 112
125000005605 benzo group Chemical group 0.000 claims description 100
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 90
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 86
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 62
125000000217 alkyl group Chemical group 0.000 claims description 55
229910052739 hydrogen Inorganic materials 0.000 claims description 48
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 45
229910052757 nitrogen Inorganic materials 0.000 claims description 39
125000000623 heterocyclic group Chemical group 0.000 claims description 35
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 30
125000004432 carbon atom Chemical group C* 0.000 claims description 25
125000001424 substituent group Chemical group 0.000 claims description 23
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical class NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 21
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 21
150000002367 halogens Chemical group 0.000 claims description 21
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 21
150000001408 amides Chemical class 0.000 claims description 20
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 19
239000002253 acid Substances 0.000 claims description 18
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 17
229920006395 saturated elastomer Polymers 0.000 claims description 17
229910052736 halogen Inorganic materials 0.000 claims description 16
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 16
125000001072 heteroaryl group Chemical group 0.000 claims description 15
150000003839 salts Chemical class 0.000 claims description 15
239000001257 hydrogen Substances 0.000 claims description 14
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 14
239000000460 chlorine Substances 0.000 claims description 13
229910052801 chlorine Inorganic materials 0.000 claims description 13
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 12
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 12
208000021302 gastroesophageal reflux disease Diseases 0.000 claims description 11
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 10
208000008469 Peptic Ulcer Diseases 0.000 claims description 10
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 10
229910052794 bromium Inorganic materials 0.000 claims description 10
125000002541 furyl group Chemical group 0.000 claims description 10
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 10
AQYSYJUIMQTRMV-UHFFFAOYSA-N hypofluorous acid Chemical compound FO AQYSYJUIMQTRMV-UHFFFAOYSA-N 0.000 claims description 10
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 10
125000001544 thienyl group Chemical group 0.000 claims description 10
125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 claims description 9
125000006163 5-membered heteroaryl group Chemical group 0.000 claims description 9
125000000753 cycloalkyl group Chemical group 0.000 claims description 8
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 8
150000002148 esters Chemical class 0.000 claims description 7
150000002430 hydrocarbons Chemical class 0.000 claims description 7
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 6
208000019901 Anxiety disease Diseases 0.000 claims description 6
239000004215 Carbon black (E152) Substances 0.000 claims description 6
208000002193 Pain Diseases 0.000 claims description 6
206010061902 Pancreatic neoplasm Diseases 0.000 claims description 6
125000004566 azetidin-1-yl group Chemical group N1(CCC1)* 0.000 claims description 6
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 6
125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 claims description 6
150000004677 hydrates Chemical class 0.000 claims description 6
229930195733 hydrocarbon Natural products 0.000 claims description 6
125000004464 hydroxyphenyl group Chemical group 0.000 claims description 6
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 6
125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
230000036407 pain Effects 0.000 claims description 6
201000002528 pancreatic cancer Diseases 0.000 claims description 6
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 6
125000004076 pyridyl group Chemical group 0.000 claims description 6
125000000714 pyrimidinyl group Chemical group 0.000 claims description 6
239000012453 solvate Substances 0.000 claims description 6
125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 5
206010052747 Adenocarcinoma pancreas Diseases 0.000 claims description 5
206010009944 Colon cancer Diseases 0.000 claims description 5
206010061968 Gastric neoplasm Diseases 0.000 claims description 5
230000036506 anxiety Effects 0.000 claims description 5
150000001721 carbon Chemical group 0.000 claims description 5
208000029742 colonic neoplasm Diseases 0.000 claims description 5
ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 claims description 5
231100000029 gastro-duodenal ulcer Toxicity 0.000 claims description 5
229910052760 oxygen Inorganic materials 0.000 claims description 5
201000002094 pancreatic adenocarcinoma Diseases 0.000 claims description 5
208000000689 peptic esophagitis Diseases 0.000 claims description 5
230000002265 prevention Effects 0.000 claims description 5
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 4
125000000066 S-methyl group Chemical group [H]C([H])([H])S* 0.000 claims description 4
125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 4
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
201000000052 gastrinoma Diseases 0.000 claims description 4
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 4
125000006533 methyl amino methyl group Chemical group [H]N(C([H])([H])[H])C([H])([H])* 0.000 claims description 4
125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 claims description 4
239000008194 pharmaceutical composition Substances 0.000 claims description 4
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 4
125000004368 propenyl group Chemical group C(=CC)* 0.000 claims description 4
125000004571 thiomorpholin-4-yl group Chemical group N1(CCSCC1)* 0.000 claims description 4
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 4
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 4
125000006507 2,4-difluorobenzyl group Chemical group [H]C1=C(F)C([H])=C(F)C(=C1[H])C([H])([H])* 0.000 claims description 3
125000006179 2-methyl benzyl group Chemical group [H]C1=C([H])C(=C(C([H])=C1[H])C([H])([H])*)C([H])([H])[H] 0.000 claims description 3
125000006512 3,4-dichlorobenzyl group Chemical group [H]C1=C(Cl)C(Cl)=C([H])C(=C1[H])C([H])([H])* 0.000 claims description 3
208000023514 Barrett esophagus Diseases 0.000 claims description 3
208000023665 Barrett oesophagus Diseases 0.000 claims description 3
208000020289 C-cell hyperplasia Diseases 0.000 claims description 3
208000030814 Eating disease Diseases 0.000 claims description 3
208000019454 Feeding and Eating disease Diseases 0.000 claims description 3
208000031845 Pernicious anaemia Diseases 0.000 claims description 3
206010070568 Thyroid C-cell hyperplasia Diseases 0.000 claims description 3
201000008629 Zollinger-Ellison syndrome Diseases 0.000 claims description 3
125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
239000003085 diluting agent Substances 0.000 claims description 3
235000014632 disordered eating Nutrition 0.000 claims description 3
125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 claims description 3
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims description 3
229910052698 phosphorus Inorganic materials 0.000 claims description 3
125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims description 3
LDMOEFOXLIZJOW-UHFFFAOYSA-N 1-dodecanesulfonic acid Chemical compound CCCCCCCCCCCCS(O)(=O)=O LDMOEFOXLIZJOW-UHFFFAOYSA-N 0.000 claims description 2
125000004562 2,3-dihydroindol-1-yl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 2
125000006508 2,6-difluorobenzyl group Chemical group [H]C1=C([H])C(F)=C(C(F)=C1[H])C([H])([H])* 0.000 claims description 2
125000006280 2-bromobenzyl group Chemical group [H]C1=C([H])C(Br)=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
125000006282 2-chlorobenzyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
125000004847 2-fluorobenzyl group Chemical group [H]C1=C([H])C(F)=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
125000006494 2-trifluoromethyl benzyl group Chemical group [H]C1=C([H])C([H])=C(C(=C1[H])C([H])([H])*)C(F)(F)F 0.000 claims description 2
125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 claims description 2
125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims description 2
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 2
BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 claims description 2
KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims description 2
101150004624 Cst8 gene Proteins 0.000 claims description 2
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 2
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 2
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 2
JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 claims description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 2
229910002651 NO3 Inorganic materials 0.000 claims description 2
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims description 2
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 2
229910019142 PO4 Inorganic materials 0.000 claims description 2
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 2
DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims description 2
125000003282 alkyl amino group Chemical group 0.000 claims description 2
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 2
125000004369 butenyl group Chemical group C(=CCC)* 0.000 claims description 2
FATUQANACHZLRT-KMRXSBRUSA-L calcium glucoheptonate Chemical compound [Ca+2].OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)C([O-])=O.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)C([O-])=O FATUQANACHZLRT-KMRXSBRUSA-L 0.000 claims description 2
125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims description 2
125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims description 2
125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 claims description 2
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 2
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 2
230000006806 disease prevention Effects 0.000 claims description 2
POULHZVOKOAJMA-UHFFFAOYSA-M dodecanoate Chemical compound CCCCCCCCCCCC([O-])=O POULHZVOKOAJMA-UHFFFAOYSA-M 0.000 claims description 2
125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 2
IPCSVZSSVZVIGE-UHFFFAOYSA-M hexadecanoate Chemical compound CCCCCCCCCCCCCCCC([O-])=O IPCSVZSSVZVIGE-UHFFFAOYSA-M 0.000 claims description 2
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 claims description 2
125000004129 indan-1-yl group Chemical group [H]C1=C([H])C([H])=C2C(=C1[H])C([H])([H])C([H])([H])C2([H])* 0.000 claims description 2
229910052740 iodine Inorganic materials 0.000 claims description 2
239000011630 iodine Substances 0.000 claims description 2
229940070765 laurate Drugs 0.000 claims description 2
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 2
125000005487 naphthalate group Chemical group 0.000 claims description 2
229940049964 oleate Drugs 0.000 claims description 2
ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims description 2
208000011906 peptic ulcer disease Diseases 0.000 claims description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 2
239000010452 phosphate Substances 0.000 claims description 2
125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 claims description 2
KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 claims description 2
229940095064 tartrate Drugs 0.000 claims description 2
125000005302 thiazolylmethyl group Chemical group [H]C1=C([H])N=C(S1)C([H])([H])* 0.000 claims description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 2
229940070710 valerate Drugs 0.000 claims description 2
NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims description 2
125000001183 hydrocarbyl group Chemical group 0.000 claims 5
125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 3
241000124008 Mammalia Species 0.000 claims 3
FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims 2
125000001624 naphthyl group Chemical group 0.000 claims 2
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical compound N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 claims 1
125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 claims 1
241001444063 Aronia Species 0.000 claims 1
235000009025 Carya illinoensis Nutrition 0.000 claims 1
241001453450 Carya illinoinensis Species 0.000 claims 1
102100032050 Elongation of very long chain fatty acids protein 2 Human genes 0.000 claims 1
241000792859 Enema Species 0.000 claims 1
101000921368 Homo sapiens Elongation of very long chain fatty acids protein 2 Proteins 0.000 claims 1
125000003342 alkenyl group Chemical group 0.000 claims 1
125000000304 alkynyl group Chemical group 0.000 claims 1
125000004429 atom Chemical group 0.000 claims 1
HSUGRBWQSSZJOP-RTWAWAEBSA-N diltiazem Chemical group C1=CC(OC)=CC=C1[C@H]1[C@@H](OC(C)=O)C(=O)N(CCN(C)C)C2=CC=CC=C2S1 HSUGRBWQSSZJOP-RTWAWAEBSA-N 0.000 claims 1
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125000005842 heteroatom Chemical group 0.000 claims 1
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239000012071 phase Substances 0.000 description 178
238000004128 high performance liquid chromatography Methods 0.000 description 160
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 112
102100026933 Myelin-associated neurite-outgrowth inhibitor Human genes 0.000 description 102
150000002500 ions Chemical class 0.000 description 76
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238000000132 electrospray ionisation Methods 0.000 description 57
239000007787 solid Substances 0.000 description 57
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 56
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 55
239000000741 silica gel Substances 0.000 description 50
229910002027 silica gel Inorganic materials 0.000 description 50
239000000243 solution Substances 0.000 description 49
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239000011541 reaction mixture Substances 0.000 description 46
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/14—Thiadiazoles; Hydrogenated thiadiazoles 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
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A—HUMAN NECESSITIES
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- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
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- A61P1/18—Drugs for disorders of the alimentary tract or the digestive system for pancreatic disorders, e.g. pancreatic enzymes
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/06—Antianaemics
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/10—1,2,5-Thiadiazoles; Hydrogenated 1,2,5-thiadiazoles
- 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

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

UAA200509353A 2003-03-28 2004-03-26 Benzo [1,2,5] thiadiazole compounds UA82872C2 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US45863803P	2003-03-28	2003-03-28
PCT/US2004/009589 WO2005012275A2 (en)	2003-03-28	2004-03-26	Benzo [1, 2, 5] thiadiazole compounds as cck2 modulators

Publications (1)

Publication Number	Publication Date
UA82872C2 true UA82872C2 (en)	2008-05-26

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ID=34115280

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
UAA200509353A UA82872C2 (en)	2003-03-28	2004-03-26	Benzo [1,2,5] thiadiazole compounds

Country Status (20)

Country	Link
US (2)	US7241759B2 (xx)
EP (1)	EP1675837A2 (xx)
JP (1)	JP2006528241A (xx)
KR (1)	KR20050119666A (xx)
CN (1)	CN1829704A (xx)
AU (1)	AU2004261547A1 (xx)
BR (1)	BRPI0408899A (xx)
CA (1)	CA2520546A1 (xx)
CO (1)	CO5700819A2 (xx)
CR (1)	CR8009A (xx)
EC (1)	ECSP056057A (xx)
IS (1)	IS8042A (xx)
MX (1)	MXPA05010484A (xx)
NO (1)	NO20055002L (xx)
NZ (1)	NZ542491A (xx)
RS (1)	RS20050733A (xx)
RU (1)	RU2005133206A (xx)
UA (1)	UA82872C2 (xx)
WO (1)	WO2005012275A2 (xx)
ZA (1)	ZA200508732B (xx)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
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WO2005085188A2 (en) *	2004-03-02	2005-09-15	Compass Pharmaceuticals Llc	Compounds and methods for anti-tumor therapy
WO2006036670A1 (en)	2004-09-24	2006-04-06	Janssen Pharmaceutica, N.V.	Sulfonamide compounds
US7599588B2 (en) *	2005-11-22	2009-10-06	Vascular Imaging Corporation	Optical imaging probe connector
EP1795198A1 (en) *	2005-12-09	2007-06-13	Hubrecht Laboratorium	Treatment of Barret's esophagus
WO2008124518A1 (en) *	2007-04-03	2008-10-16	Janssen Pharmaceutica N.V.	Oxo-dihydroisoindole sulfonamide compounds as modulators of the cck2 receptor
EP2053052A1 (en) *	2007-10-23	2009-04-29	Laboratorios del Dr. Esteve S.A.	Process for the preparation of 6-substituted imidazo[2,1-b]thiazole-5-sulfonyl halide
EP3708169A1 (en) *	2009-06-29	2020-09-16	Agios Pharmaceuticals, Inc.	2,3-dihydrobenzo[b][1,4]dioxine-6-sulfonamide derivatives having an anticancer activity
RU2532492C1 (ru) *	2013-01-28	2014-11-10	Государственное бюджетное образовательное учреждение высшего профессионального образования "Воронежская государственная медицинская академия им. Н.Н. Бурденко" Министерства здравоохранения Российской Федерации	Способ эндоскопического лечения гастродуоденальных язв
DK3071206T3 (da)	2013-11-22	2021-05-25	CL BioSciences LLC	Gastrinantagonister (eg yf476, netazepid) til behandling og forebyggelse af osteoporose

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FR2703995B1 (fr)	1993-04-16	1995-07-21	Sanofi Elf	5-acylamino 1,2,4-thiadiazoles, leur preparation et compositions pharmaceutiques en contenant.
US6239131B1 (en)	1996-12-10	2001-05-29	Zeria Pharmaceutical Co., Ltd.	1,5 Benzodiazepine derivatives
HUP0202142A3 (en) *	1999-06-24	2005-05-30	Smithkline Beecham Corp Philap	Macrophage scavenger receptor antagonists
GB0028702D0 (en)	2000-11-24	2001-01-10	Novartis Ag	Organic compounds
WO2002090353A1 (en)	2001-05-07	2002-11-14	Smithkline Beecham Corporation	Sulfonamides
ITTO20020674A1 (it)	2002-07-26	2004-01-26	Rotta Research Lab	Derivati antranilici ad attivita' anticolecistochininica (anti-cck-1), procedimento per la loro preparazione e loro uso farmaceutico

2004
- 2004-03-26 WO PCT/US2004/009589 patent/WO2005012275A2/en active Application Filing
- 2004-03-26 AU AU2004261547A patent/AU2004261547A1/en not_active Abandoned
- 2004-03-26 UA UAA200509353A patent/UA82872C2/uk unknown
- 2004-03-26 CN CNA2004800144708A patent/CN1829704A/zh active Pending
- 2004-03-26 CA CA002520546A patent/CA2520546A1/en not_active Abandoned
- 2004-03-26 MX MXPA05010484A patent/MXPA05010484A/es unknown
- 2004-03-26 NZ NZ542491A patent/NZ542491A/en unknown
- 2004-03-26 RS YUP-2005/0733A patent/RS20050733A/sr unknown
- 2004-03-26 JP JP2006532352A patent/JP2006528241A/ja not_active Withdrawn
- 2004-03-26 EP EP04785868A patent/EP1675837A2/en not_active Withdrawn
- 2004-03-26 KR KR1020057018397A patent/KR20050119666A/ko not_active Application Discontinuation
- 2004-03-26 RU RU2005133206/04A patent/RU2005133206A/ru not_active Application Discontinuation
- 2004-03-26 US US10/811,292 patent/US7241759B2/en active Active
- 2004-03-26 BR BRPI0408899-9A patent/BRPI0408899A/pt not_active IP Right Cessation
2005
- 2005-09-23 IS IS8042A patent/IS8042A/is unknown
- 2005-09-28 EC EC2005006057A patent/ECSP056057A/es unknown
- 2005-09-28 CR CR8009A patent/CR8009A/es unknown
- 2005-10-05 CO CO05100979A patent/CO5700819A2/es not_active Application Discontinuation
- 2005-10-27 NO NO20055002A patent/NO20055002L/no not_active Application Discontinuation
- 2005-10-27 ZA ZA200508732A patent/ZA200508732B/en unknown
2007
- 2007-07-10 US US11/775,535 patent/US7550492B2/en not_active Expired - Lifetime

Also Published As

Publication number	Publication date
US7241759B2 (en)	2007-07-10
NO20055002D0 (no)	2005-10-27
WO2005012275A2 (en)	2005-02-10
RS20050733A (xx)	2007-06-04
NO20055002L (no)	2005-12-14
WO2005012275A3 (en)	2006-05-11
CO5700819A2 (es)	2006-11-30
AU2004261547A1 (en)	2005-02-10
ECSP056057A (es)	2006-01-27
KR20050119666A (ko)	2005-12-21
NZ542491A (en)	2009-04-30
BRPI0408899A (pt)	2006-04-18
EP1675837A2 (en)	2006-07-05
RU2005133206A (ru)	2006-05-10
US7550492B2 (en)	2009-06-23
US20070276016A1 (en)	2007-11-29
CR8009A (es)	2008-09-10
ZA200508732B (en)	2007-04-25
CA2520546A1 (en)	2005-02-10
MXPA05010484A (es)	2006-03-10
US20040224983A1 (en)	2004-11-11
IS8042A (is)	2005-09-23
CN1829704A (zh)	2006-09-06
JP2006528241A (ja)	2006-12-14

Publication	Publication Date	Title
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US7368444B2 (en)	2008-05-06	N-carbamoyl nitrogen-containing fused ring compounds and drugs containing these compounds as the active ingredient
US7550492B2 (en)	2009-06-23	Benzo[1,2,5]thiadiazole compounds
EA015516B1 (ru)	2011-08-30	Ингибиторы 11-бета-гидроксистероид дегидрогеназы 1
TW201000460A (en)	2010-01-01	Amide compound
JP2002529464A (ja)	2002-09-10	Ｙ５受容体拮抗薬としてのスピロインドリン類
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JP2502343B2 (ja)	1996-05-29	薬学的に活性な置換ベンズアミド
JP2002522532A (ja)	2002-07-23	カルシウム分解化合物
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EP2261206A1 (en)	2010-12-15	Indolinone compound
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JP2007504263A (ja)	2007-03-01	オキシトシン作働薬としてのピペラジン類
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EP0148201A1 (en)	1985-07-17	Naphtalene aminoalkylene ethers and thioethers, and their pharma ceutical uses
EA037040B1 (ru)	2021-01-29	Асимметричные бензолсульфонилмочевины и их применение в качестве модуляторов рецептора грелина
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AU2862184A (en)	1984-11-19	Naphthalene aminoalkylene ethers and thioethers, and their pharmaceutical uses
JPH1053528A (ja)	1998-02-24	６−メトキシ−１ｈ−ベンゾトリアゾール−５−カルボキサミド誘導体からなる医薬