SK8452002A3 - Substituted 4-(phenyl or pyridyl)imidazole derivatives, pharmaceutical composition comprising the same and use thereof - Google Patents

Substituted 4-(phenyl or pyridyl)imidazole derivatives, pharmaceutical composition comprising the same and use thereof Download PDF

Info

Publication number: SK8452002A3
Authority: SK; Slovakia
Prior art keywords: alkyl; mmol; phenyl; pyridyl; product
Prior art date: 1999-12-16

Application number

SK845-2002A

Other languages

English (en)

Slovak (sk)

Inventor

Andrew W Stamford

Craig D Boyle

Ying Huang

Original Assignee

Schering Corp

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.)

1999-12-16

Filing date

2000-12-14

Publication date

2002-11-06

2000-12-14 Application filed by Schering Corp filed Critical Schering Corp

2002-11-06 Publication of SK8452002A3 publication Critical patent/SK8452002A3/sk

Links

125000004076 pyridyl group Chemical group 0.000 title claims abstract description 24
239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 16
150000001875 compounds Chemical class 0.000 claims abstract description 99
125000000217 alkyl group Chemical group 0.000 claims abstract description 75
-1 phenylthioalkyl Chemical group 0.000 claims abstract description 37
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 25
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 24
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 19
125000000592 heterocycloalkyl group Chemical group 0.000 claims abstract description 13
239000001257 hydrogen Substances 0.000 claims abstract description 13
150000003839 salts Chemical class 0.000 claims abstract description 10
206010012601 diabetes mellitus Diseases 0.000 claims abstract description 9
150000002431 hydrogen Chemical class 0.000 claims abstract description 9
229910052736 halogen Inorganic materials 0.000 claims abstract description 8
150000002367 halogens Chemical class 0.000 claims abstract description 8
125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims abstract description 7
125000004385 trihaloalkyl group Chemical group 0.000 claims abstract description 4
125000003342 alkenyl group Chemical group 0.000 claims abstract description 3
239000012453 solvate Substances 0.000 claims abstract description 3
150000002460 imidazoles Chemical class 0.000 claims description 25
125000001072 heteroaryl group Chemical group 0.000 claims description 24
125000003118 aryl group Chemical group 0.000 claims description 23
229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 claims description 16
125000001424 substituent group Chemical group 0.000 claims description 12
229910052757 nitrogen Inorganic materials 0.000 claims description 10
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
125000004432 carbon atom Chemical group C* 0.000 claims description 6
239000003937 drug carrier Substances 0.000 claims description 6
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 6
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
125000003545 alkoxy group Chemical group 0.000 claims description 4
229910052799 carbon Inorganic materials 0.000 claims description 4
125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 3
125000004487 4-tetrahydropyranyl group Chemical group [H]C1([H])OC([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
150000001204 N-oxides Chemical class 0.000 claims description 2
125000005037 alkyl phenyl group Chemical group 0.000 claims description 2
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims description 2
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
239000003814 drug Substances 0.000 claims 2
125000002947 alkylene group Chemical group 0.000 claims 1
238000000034 method Methods 0.000 abstract description 54
208000030814 Eating disease Diseases 0.000 abstract description 6
208000019454 Feeding and Eating disease Diseases 0.000 abstract description 6
235000014632 disordered eating Nutrition 0.000 abstract description 6
125000003373 pyrazinyl group Chemical group 0.000 abstract description 2
125000000335 thiazolyl group Chemical group 0.000 abstract description 2
125000001544 thienyl group Chemical group 0.000 abstract description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract description 2
FTAHXMZRJCZXDL-UHFFFAOYSA-N 3-piperideine Chemical compound C1CC=CCN1 FTAHXMZRJCZXDL-UHFFFAOYSA-N 0.000 abstract 1
125000005885 heterocycloalkylalkyl group Chemical group 0.000 abstract 1
125000005359 phenoxyalkyl group Chemical group 0.000 abstract 1
239000000460 chlorine Substances 0.000 description 173
239000000047 product Substances 0.000 description 164
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 112
239000000243 solution Substances 0.000 description 80
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 78
239000000203 mixture Substances 0.000 description 77
238000005481 NMR spectroscopy Methods 0.000 description 57
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 53
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 50
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 48
239000011541 reaction mixture Substances 0.000 description 47
238000012746 preparative thin layer chromatography Methods 0.000 description 45
239000012044 organic layer Substances 0.000 description 44
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 40
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 31
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 27
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 27
235000011121 sodium hydroxide Nutrition 0.000 description 26
238000000746 purification Methods 0.000 description 25
238000006243 chemical reaction Methods 0.000 description 24
238000002360 preparation method Methods 0.000 description 21
239000007858 starting material Substances 0.000 description 18
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 17
238000004992 fast atom bombardment mass spectroscopy Methods 0.000 description 16
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 15
239000000706 filtrate Substances 0.000 description 15
238000003818 flash chromatography Methods 0.000 description 14
MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 14
239000007787 solid Substances 0.000 description 14
238000005160 1H NMR spectroscopy Methods 0.000 description 13
101710151321 Melanostatin Proteins 0.000 description 13
102400000064 Neuropeptide Y Human genes 0.000 description 13
URPYMXQQVHTUDU-OFGSCBOVSA-N nucleopeptide y Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(N)=O)NC(=O)[C@H](CC=1NC=NC=1)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](C)NC(=O)[C@H](CO)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)CNC(=O)[C@H]1N(CCC1)C(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CCCCN)NC(=O)[C@H](CO)NC(=O)[C@H]1N(CCC1)C(=O)[C@@H](N)CC=1C=CC(O)=CC=1)C1=CC=C(O)C=C1 URPYMXQQVHTUDU-OFGSCBOVSA-N 0.000 description 13
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 11
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 10
239000005557 antagonist Substances 0.000 description 9
239000010410 layer Substances 0.000 description 9
FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 9
102100029549 Neuropeptide Y receptor type 5 Human genes 0.000 description 8
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
229920006395 saturated elastomer Polymers 0.000 description 8
239000011734 sodium Substances 0.000 description 8
238000004440 column chromatography Methods 0.000 description 7
238000010992 reflux Methods 0.000 description 7
229910000104 sodium hydride Inorganic materials 0.000 description 7
BPXKZEMBEZGUAH-UHFFFAOYSA-N 2-(chloromethoxy)ethyl-trimethylsilane Chemical compound C[Si](C)(C)CCOCCl BPXKZEMBEZGUAH-UHFFFAOYSA-N 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 6
101710198055 Neuropeptide Y receptor type 5 Proteins 0.000 description 6
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 6
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 6
239000012280 lithium aluminium hydride Substances 0.000 description 6
YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 6
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
238000003756 stirring Methods 0.000 description 6
239000000725 suspension Substances 0.000 description 6
KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 5
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 5
GELXFVQAWNTGPQ-UHFFFAOYSA-N [N].C1=CNC=N1 Chemical compound [N].C1=CNC=N1 GELXFVQAWNTGPQ-UHFFFAOYSA-N 0.000 description 5
125000002883 imidazolyl group Chemical group 0.000 description 5
239000007788 liquid Substances 0.000 description 5
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 4
206010020710 Hyperphagia Diseases 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
XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
239000002253 acid Substances 0.000 description 4
150000001409 amidines Chemical class 0.000 description 4
150000001412 amines Chemical class 0.000 description 4
239000012131 assay buffer Substances 0.000 description 4
MUALRAIOVNYAIW-UHFFFAOYSA-N binap Chemical group C1=CC=CC=C1P(C=1C(=C2C=CC=CC2=CC=1)C=1C2=CC=CC=C2C=CC=1P(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 MUALRAIOVNYAIW-UHFFFAOYSA-N 0.000 description 4
210000004027 cell Anatomy 0.000 description 4
238000010511 deprotection reaction Methods 0.000 description 4
239000000839 emulsion Substances 0.000 description 4
YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical compound [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 description 4
229910052763 palladium Inorganic materials 0.000 description 4
229910000027 potassium carbonate Inorganic materials 0.000 description 4
239000000843 powder Substances 0.000 description 4
239000003039 volatile agent Substances 0.000 description 4
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 3
LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Substances CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 3
IMRWILPUOVGIMU-UHFFFAOYSA-N 2-bromopyridine Chemical compound BrC1=CC=CC=N1 IMRWILPUOVGIMU-UHFFFAOYSA-N 0.000 description 3
FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 3
KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Natural products CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 3
208000008589 Obesity Diseases 0.000 description 3
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
239000004480 active ingredient Substances 0.000 description 3
150000001263 acyl chlorides Chemical class 0.000 description 3
230000027455 binding Effects 0.000 description 3
239000012267 brine Substances 0.000 description 3
125000002837 carbocyclic group Chemical group 0.000 description 3
230000000875 corresponding effect Effects 0.000 description 3
230000008878 coupling Effects 0.000 description 3
238000010168 coupling process Methods 0.000 description 3
238000005859 coupling reaction Methods 0.000 description 3
239000012043 crude product Substances 0.000 description 3
230000000694 effects Effects 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
239000012065 filter cake Substances 0.000 description 3
239000012458 free base Substances 0.000 description 3
125000005842 heteroatom Chemical group 0.000 description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
239000005457 ice water Substances 0.000 description 3
235000020824 obesity Nutrition 0.000 description 3
125000003386 piperidinyl group Chemical group 0.000 description 3
235000011181 potassium carbonates Nutrition 0.000 description 3
108090000765 processed proteins & peptides Proteins 0.000 description 3
125000006239 protecting group Chemical group 0.000 description 3
230000002829 reductive effect Effects 0.000 description 3
239000012321 sodium triacetoxyborohydride Substances 0.000 description 3
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
238000004809 thin layer chromatography Methods 0.000 description 3
CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 2
VUCWMAJEUOWLEY-UHFFFAOYSA-N 1-$l^{1}-azanylpiperidine Chemical compound [N]N1CCCCC1 VUCWMAJEUOWLEY-UHFFFAOYSA-N 0.000 description 2
QKWWDTYDYOFRJL-UHFFFAOYSA-N 2,2-dimethoxyethanamine Chemical compound COC(CN)OC QKWWDTYDYOFRJL-UHFFFAOYSA-N 0.000 description 2
JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 2
LRLQQERNMXHASR-UHFFFAOYSA-N 2-diphenylphosphanylpropan-2-yl(diphenyl)phosphane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)C(C)(C)P(C=1C=CC=CC=1)C1=CC=CC=C1 LRLQQERNMXHASR-UHFFFAOYSA-N 0.000 description 2
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 2
229960000549 4-dimethylaminophenol Drugs 0.000 description 2
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 2
239000005695 Ammonium acetate Substances 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
OHCQJHSOBUTRHG-KGGHGJDLSA-N FORSKOLIN Chemical compound O=C([C@@]12O)C[C@](C)(C=C)O[C@]1(C)[C@@H](OC(=O)C)[C@@H](O)[C@@H]1[C@]2(C)[C@@H](O)CCC1(C)C OHCQJHSOBUTRHG-KGGHGJDLSA-N 0.000 description 2
239000007995 HEPES buffer Substances 0.000 description 2
239000012981 Hank's balanced salt solution Substances 0.000 description 2
101000633401 Homo sapiens Neuropeptide Y receptor type 5 Proteins 0.000 description 2
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 2
239000012359 Methanesulfonyl chloride Substances 0.000 description 2
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
239000000443 aerosol Substances 0.000 description 2
239000000556 agonist Substances 0.000 description 2
229940043376 ammonium acetate Drugs 0.000 description 2
235000019257 ammonium acetate Nutrition 0.000 description 2
125000003710 aryl alkyl group Chemical group 0.000 description 2
238000003556 assay Methods 0.000 description 2
239000002585 base Substances 0.000 description 2
HSDAJNMJOMSNEV-UHFFFAOYSA-N benzyl chloroformate Chemical compound ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
239000002775 capsule Substances 0.000 description 2
RBHJBMIOOPYDBQ-UHFFFAOYSA-N carbon dioxide;propan-2-one Chemical compound O=C=O.CC(C)=O RBHJBMIOOPYDBQ-UHFFFAOYSA-N 0.000 description 2
239000013553 cell monolayer Substances 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
210000004978 chinese hamster ovary cell Anatomy 0.000 description 2
OHCQJHSOBUTRHG-UHFFFAOYSA-N colforsin Natural products OC12C(=O)CC(C)(C=C)OC1(C)C(OC(=O)C)C(O)C1C2(C)C(O)CCC1(C)C OHCQJHSOBUTRHG-UHFFFAOYSA-N 0.000 description 2
238000001816 cooling Methods 0.000 description 2
NXQGGXCHGDYOHB-UHFFFAOYSA-L cyclopenta-1,4-dien-1-yl(diphenyl)phosphane;dichloropalladium;iron(2+) Chemical compound [Fe+2].Cl[Pd]Cl.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 NXQGGXCHGDYOHB-UHFFFAOYSA-L 0.000 description 2
229940043279 diisopropylamine Drugs 0.000 description 2
ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
239000006185 dispersion Substances 0.000 description 2
BRZYSWJRSDMWLG-CAXSIQPQSA-N geneticin Chemical compound O1C[C@@](O)(C)[C@H](NC)[C@@H](O)[C@H]1O[C@@H]1[C@@H](O)[C@H](O[C@@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](C(C)O)O2)N)[C@@H](N)C[C@H]1N BRZYSWJRSDMWLG-CAXSIQPQSA-N 0.000 description 2
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HNXZSRFTSWZMAG-UHFFFAOYSA-N 1,2,3,6-tetrahydropyridin-4-yl trifluoromethanesulfonate Chemical compound FC(F)(F)S(=O)(=O)OC1=CCNCC1 HNXZSRFTSWZMAG-UHFFFAOYSA-N 0.000 description 1
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
UKSZBOKPHAQOMP-UHFFFAOYSA-N 1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].C=1C=CC=CC=1C=CC(=O)C=CC1=CC=CC=C1.C=1C=CC=CC=1C=CC(=O)C=CC1=CC=CC=C1 UKSZBOKPHAQOMP-UHFFFAOYSA-N 0.000 description 1
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RXNZFHIEDZEUQM-UHFFFAOYSA-N 2-bromo-1,3-thiazole Chemical compound BrC1=NC=CS1 RXNZFHIEDZEUQM-UHFFFAOYSA-N 0.000 description 1
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APIXJSLKIYYUKG-UHFFFAOYSA-N 3 Isobutyl 1 methylxanthine Chemical compound O=C1N(C)C(=O)N(CC(C)C)C2=C1N=CN2 APIXJSLKIYYUKG-UHFFFAOYSA-N 0.000 description 1
STXAVEHFKAXGOX-UHFFFAOYSA-N 3-bromobenzonitrile Chemical compound BrC1=CC=CC(C#N)=C1 STXAVEHFKAXGOX-UHFFFAOYSA-N 0.000 description 1
KWAYEPXDGHYGRW-UHFFFAOYSA-N 3-nitrobenzamide Chemical compound NC(=O)C1=CC=CC([N+]([O-])=O)=C1 KWAYEPXDGHYGRW-UHFFFAOYSA-N 0.000 description 1
GZPHSAQLYPIAIN-UHFFFAOYSA-N 3-pyridinecarbonitrile Chemical compound N#CC1=CC=CN=C1 GZPHSAQLYPIAIN-UHFFFAOYSA-N 0.000 description 1
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 1
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
FHZALEJIENDROK-UHFFFAOYSA-N 5-bromo-1h-imidazole Chemical class BrC1=CN=CN1 FHZALEJIENDROK-UHFFFAOYSA-N 0.000 description 1
FTFFHWWIPOQCBC-UHFFFAOYSA-N 5-bromopyridine-3-carbonitrile Chemical compound BrC1=CN=CC(C#N)=C1 FTFFHWWIPOQCBC-UHFFFAOYSA-N 0.000 description 1
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ORIQLMBUPMABDV-UHFFFAOYSA-N 6-chloropyridine-3-carbonitrile Chemical compound ClC1=CC=C(C#N)C=N1 ORIQLMBUPMABDV-UHFFFAOYSA-N 0.000 description 1
AMKGKYQBASDDJB-UHFFFAOYSA-N 9$l^{2}-borabicyclo[3.3.1]nonane Chemical compound C1CCC2CCCC1[B]2 AMKGKYQBASDDJB-UHFFFAOYSA-N 0.000 description 1
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CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical compound NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
SUZLHDUTVMZSEV-UHFFFAOYSA-N Deoxycoleonol Natural products C12C(=O)CC(C)(C=C)OC2(C)C(OC(=O)C)C(O)C2C1(C)C(O)CCC2(C)C SUZLHDUTVMZSEV-UHFFFAOYSA-N 0.000 description 1
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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 1
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229910005948 SO2Cl Inorganic materials 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
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238000006297 dehydration reaction Methods 0.000 description 1
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SXZIXHOMFPUIRK-UHFFFAOYSA-N diphenylmethanimine Chemical compound C=1C=CC=CC=1C(=N)C1=CC=CC=C1 SXZIXHOMFPUIRK-UHFFFAOYSA-N 0.000 description 1
LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 1
238000010494 dissociation reaction Methods 0.000 description 1
230000005593 dissociations Effects 0.000 description 1
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238000001914 filtration Methods 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
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238000009472 formulation Methods 0.000 description 1
125000002541 furyl group Chemical group 0.000 description 1
239000007789 gas Substances 0.000 description 1
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239000003365 glass fiber Substances 0.000 description 1
239000008187 granular material Substances 0.000 description 1
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238000005984 hydrogenation reaction Methods 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
OWFXIOWLTKNBAP-UHFFFAOYSA-N isoamyl nitrite Chemical compound CC(C)CCON=O OWFXIOWLTKNBAP-UHFFFAOYSA-N 0.000 description 1
125000000842 isoxazolyl group Chemical group 0.000 description 1
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239000008101 lactose Substances 0.000 description 1
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239000001095 magnesium carbonate Substances 0.000 description 1
229910000021 magnesium carbonate Inorganic materials 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
239000011159 matrix material Substances 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
125000002757 morpholinyl group Chemical group 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
DASJFYAPNPUBGG-UHFFFAOYSA-N naphthalene-1-sulfonyl chloride Chemical compound C1=CC=C2C(S(=O)(=O)Cl)=CC=CC2=C1 DASJFYAPNPUBGG-UHFFFAOYSA-N 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
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125000001715 oxadiazolyl group Chemical group 0.000 description 1
125000004430 oxygen atom Chemical group O* 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
210000001428 peripheral nervous system Anatomy 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
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125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
239000002953 phosphate buffered saline Substances 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
230000001766 physiological effect Effects 0.000 description 1
150000003053 piperidines Chemical class 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
235000015320 potassium carbonate Nutrition 0.000 description 1
229910000160 potassium phosphate Inorganic materials 0.000 description 1
235000011009 potassium phosphates Nutrition 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
ALDITMKAAPLVJK-UHFFFAOYSA-N prop-1-ene;hydrate Chemical group O.CC=C ALDITMKAAPLVJK-UHFFFAOYSA-N 0.000 description 1
KPBSJEBFALFJTO-UHFFFAOYSA-N propane-1-sulfonyl chloride Chemical compound CCCS(Cl)(=O)=O KPBSJEBFALFJTO-UHFFFAOYSA-N 0.000 description 1
DNIAPMSPPWPWGF-UHFFFAOYSA-N propylene glycol Substances CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
238000000159 protein binding assay Methods 0.000 description 1
125000003226 pyrazolyl group Chemical group 0.000 description 1
125000000714 pyrimidinyl group Chemical group 0.000 description 1
125000000719 pyrrolidinyl group Chemical group 0.000 description 1
125000000168 pyrrolyl group Chemical group 0.000 description 1
238000001525 receptor binding assay Methods 0.000 description 1
238000006722 reduction reaction Methods 0.000 description 1
238000005932 reductive alkylation reaction Methods 0.000 description 1
238000006268 reductive amination reaction Methods 0.000 description 1
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230000007017 scission Effects 0.000 description 1
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229910052708 sodium Inorganic materials 0.000 description 1
235000015424 sodium Nutrition 0.000 description 1
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235000017281 sodium acetate Nutrition 0.000 description 1
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239000012312 sodium hydride Substances 0.000 description 1
SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 description 1
239000007909 solid dosage form Substances 0.000 description 1
229960005322 streptomycin Drugs 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
125000004434 sulfur atom Chemical group 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
PDTZMULNKGUIEJ-UHFFFAOYSA-N tert-butyl 4-methylidenepiperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(=C)CC1 PDTZMULNKGUIEJ-UHFFFAOYSA-N 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
238000010998 test method Methods 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
125000003831 tetrazolyl group Chemical group 0.000 description 1
238000011287 therapeutic dose Methods 0.000 description 1
230000035924 thermogenesis Effects 0.000 description 1
125000001113 thiadiazolyl group Chemical group 0.000 description 1
125000004568 thiomorpholinyl group Chemical group 0.000 description 1
125000001425 triazolyl group Chemical group 0.000 description 1
JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 1
238000010792 warming Methods 0.000 description 1
239000011592 zinc chloride Substances 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
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SK845-2002A 1999-12-16 2000-12-14 Substituted 4-(phenyl or pyridyl)imidazole derivatives, pharmaceutical composition comprising the same and use thereof SK8452002A3 (en)

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US17122399P	1999-12-16	1999-12-16
PCT/US2000/033832 WO2001044201A1 (en)	1999-12-16	2000-12-14	Substituted imidazole neuropeptide y y5 receptor antagonists

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US (2)	US6444687B1 (cs)
EP (1)	EP1237875B1 (cs)
JP (2)	JP4180276B2 (cs)
KR (1)	KR20020062342A (cs)
CN (1)	CN1227236C (cs)
AR (1)	AR032292A1 (cs)
AT (1)	ATE303364T1 (cs)
AU (1)	AU2261401A (cs)
BR (1)	BR0017025A (cs)
CA (1)	CA2393821C (cs)
CZ (1)	CZ20022100A3 (cs)
DE (1)	DE60022386T2 (cs)
ES (1)	ES2243337T3 (cs)
HK (1)	HK1045503A1 (cs)
HU (1)	HUP0301218A2 (cs)
IL (1)	IL149872A0 (cs)
MX (1)	MXPA02006016A (cs)
MY (1)	MY138524A (cs)
NO (1)	NO20022835L (cs)
NZ (1)	NZ519272A (cs)
PL (1)	PL356485A1 (cs)
RU (1)	RU2002119019A (cs)
SK (1)	SK8452002A3 (cs)
TR (1)	TR200201568T2 (cs)
WO (1)	WO2001044201A1 (cs)
ZA (1)	ZA200204350B (cs)

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- 2000-12-14 EP EP00986362A patent/EP1237875B1/en not_active Expired - Lifetime
- 2000-12-14 US US09/737,141 patent/US6444687B1/en not_active Expired - Fee Related
- 2000-12-14 KR KR1020027007619A patent/KR20020062342A/ko not_active Ceased
- 2000-12-14 AR ARP000106641A patent/AR032292A1/es unknown
- 2000-12-14 AT AT00986362T patent/ATE303364T1/de not_active IP Right Cessation
- 2000-12-14 AU AU22614/01A patent/AU2261401A/en not_active Abandoned
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- 2000-12-14 WO PCT/US2000/033832 patent/WO2001044201A1/en not_active Ceased
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- 2000-12-14 BR BR0017025-9A patent/BR0017025A/pt not_active Application Discontinuation
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- 2000-12-14 DE DE60022386T patent/DE60022386T2/de not_active Expired - Lifetime
- 2000-12-15 MY MYPI20005922A patent/MY138524A/en unknown
2002
- 2002-05-30 ZA ZA200204350A patent/ZA200204350B/en unknown
- 2002-06-14 NO NO20022835A patent/NO20022835L/no not_active Application Discontinuation
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Also Published As

Publication number	Publication date
ZA200204350B (en)	2003-09-01
ES2243337T3 (es)	2005-12-01
US6444687B1 (en)	2002-09-03
EP1237875A1 (en)	2002-09-11
TR200201568T2 (tr)	2002-10-21
PL356485A1 (en)	2004-06-28
AR032292A1 (es)	2003-11-05
MXPA02006016A (es)	2002-12-05
KR20020062342A (ko)	2002-07-25
JP2003517479A (ja)	2003-05-27
JP2006199710A (ja)	2006-08-03
US6632828B2 (en)	2003-10-14
AU2261401A (en)	2001-06-25
WO2001044201A1 (en)	2001-06-21
NO20022835D0 (no)	2002-06-14
DE60022386D1 (de)	2005-10-06
US20030114465A1 (en)	2003-06-19
CN1227236C (zh)	2005-11-16
CA2393821C (en)	2009-05-26
EP1237875B1 (en)	2005-08-31
CA2393821A1 (en)	2001-06-21
DE60022386T2 (de)	2006-06-22
NO20022835L (no)	2002-08-16
MY138524A (en)	2009-06-30
JP4180276B2 (ja)	2008-11-12
ATE303364T1 (de)	2005-09-15
NZ519272A (en)	2004-02-27
BR0017025A (pt)	2003-01-07
IL149872A0 (en)	2002-11-10
CN1434806A (zh)	2003-08-06
HK1045503A1 (zh)	2002-11-29
HUP0301218A2 (hu)	2003-08-28
RU2002119019A (ru)	2004-01-10
CZ20022100A3 (cs)	2002-09-11

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