HRP980434A2 - 4-AMINOPYRROLE (3,2-d) PYRIMIDINES AS NEUROPEPTIDE Y RECEPTOR ANTAGONISTS - Google Patents

4-AMINOPYRROLE (3,2-d) PYRIMIDINES AS NEUROPEPTIDE Y RECEPTOR ANTAGONISTS

Info

Publication number: HRP980434A2
Authority: HR; Croatia
Prior art keywords: image; methyl; alkyl; phenyl; pyrrolidin
Prior art date: 1997-08-05

Application number

HR60/054,734A

Other languages

English (en)

Croatian (hr)

Inventor

Marlys Hammond

Original Assignee

Marlys Hammond

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.)

1997-08-05

Filing date

1998-08-04

Publication date

1999-04-30

1998-08-04 Application filed by Marlys Hammond filed Critical Marlys Hammond

1999-04-30 Publication of HRP980434A2 publication Critical patent/HRP980434A2/hr

Links

WAUGGYPDCQZJKK-UHFFFAOYSA-N 1h-pyrrol-3-amine Chemical compound NC=1C=CNC=1 WAUGGYPDCQZJKK-UHFFFAOYSA-N 0.000 title description 2
150000003230 pyrimidines Chemical class 0.000 title description 2
239000002660 neuropeptide Y receptor antagonist Substances 0.000 title 1
150000001875 compounds Chemical class 0.000 description 90
238000000034 method Methods 0.000 description 32
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 23
125000004169 (C1-C6) alkyl group Chemical group 0.000 description 20
238000004949 mass spectrometry Methods 0.000 description 19
241001465754 Metazoa Species 0.000 description 17
101710151321 Melanostatin Proteins 0.000 description 16
102400000064 Neuropeptide Y Human genes 0.000 description 16
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 16
238000002360 preparation method Methods 0.000 description 15
201000010099 disease Diseases 0.000 description 14
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 13
239000000203 mixture Substances 0.000 description 13
210000004027 cell Anatomy 0.000 description 12
239000003814 drug Substances 0.000 description 12
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 12
239000000243 solution Substances 0.000 description 12
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 11
230000037396 body weight Effects 0.000 description 11
235000013305 food Nutrition 0.000 description 11
239000001257 hydrogen Substances 0.000 description 11
229910052739 hydrogen Inorganic materials 0.000 description 11
102000005962 receptors Human genes 0.000 description 11
108020003175 receptors Proteins 0.000 description 11
230000002159 abnormal effect Effects 0.000 description 10
238000006243 chemical reaction Methods 0.000 description 10
150000003839 salts Chemical class 0.000 description 10
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
239000004480 active ingredient Substances 0.000 description 9
229940079593 drug Drugs 0.000 description 9
210000000287 oocyte Anatomy 0.000 description 9
-1 2,4-dimethoxyphenyl Chemical group 0.000 description 8
125000000217 alkyl group Chemical group 0.000 description 8
239000003795 chemical substances by application Substances 0.000 description 8
230000000694 effects Effects 0.000 description 8
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
239000003826 tablet Substances 0.000 description 7
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
208000008589 Obesity Diseases 0.000 description 6
230000004913 activation Effects 0.000 description 6
235000014113 dietary fatty acids Nutrition 0.000 description 6
239000000194 fatty acid Substances 0.000 description 6
229930195729 fatty acid Natural products 0.000 description 6
150000004665 fatty acids Chemical class 0.000 description 6
235000003599 food sweetener Nutrition 0.000 description 6
150000002431 hydrogen Chemical class 0.000 description 6
125000000896 monocarboxylic acid group Chemical group 0.000 description 6
235000020824 obesity Nutrition 0.000 description 6
239000000546 pharmaceutical excipient Substances 0.000 description 6
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 6
239000003765 sweetening agent Substances 0.000 description 6
239000012591 Dulbecco’s Phosphate Buffered Saline Substances 0.000 description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
208000002193 Pain Diseases 0.000 description 5
239000000464 adrenergic agent Substances 0.000 description 5
239000003086 colorant Substances 0.000 description 5
239000007859 condensation product Substances 0.000 description 5
150000002148 esters Chemical class 0.000 description 5
238000002474 experimental method Methods 0.000 description 5
235000012054 meals Nutrition 0.000 description 5
231100000252 nontoxic Toxicity 0.000 description 5
230000003000 nontoxic effect Effects 0.000 description 5
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
239000003755 preservative agent Substances 0.000 description 5
108090000765 processed proteins & peptides Proteins 0.000 description 5
239000011780 sodium chloride Substances 0.000 description 5
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 4
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 4
206010020772 Hypertension Diseases 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
208000006011 Stroke Diseases 0.000 description 4
239000002253 acid Substances 0.000 description 4
239000011149 active material Substances 0.000 description 4
239000000556 agonist Substances 0.000 description 4
239000007900 aqueous suspension Substances 0.000 description 4
208000006673 asthma Diseases 0.000 description 4
230000027455 binding Effects 0.000 description 4
239000012148 binding buffer Substances 0.000 description 4
239000012141 concentrate Substances 0.000 description 4
235000008504 concentrate Nutrition 0.000 description 4
125000000392 cycloalkenyl group Chemical group 0.000 description 4
239000003085 diluting agent Substances 0.000 description 4
239000003937 drug carrier Substances 0.000 description 4
239000000796 flavoring agent Substances 0.000 description 4
238000009472 formulation Methods 0.000 description 4
239000005556 hormone Substances 0.000 description 4
229940088597 hormone Drugs 0.000 description 4
238000002347 injection Methods 0.000 description 4
239000007924 injection Substances 0.000 description 4
NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 4
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 4
238000002156 mixing Methods 0.000 description 4
230000036961 partial effect Effects 0.000 description 4
239000000825 pharmaceutical preparation Substances 0.000 description 4
YBYRMVIVWMBXKQ-UHFFFAOYSA-N phenylmethanesulfonyl fluoride Chemical compound FS(=O)(=O)CC1=CC=CC=C1 YBYRMVIVWMBXKQ-UHFFFAOYSA-N 0.000 description 4
102000004196 processed proteins & peptides Human genes 0.000 description 4
125000001424 substituent group Chemical group 0.000 description 4
239000000725 suspension Substances 0.000 description 4
125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 3
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 3
241000283690 Bos taurus Species 0.000 description 3
108091003079 Bovine Serum Albumin Proteins 0.000 description 3
UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 3
241000283707 Capra Species 0.000 description 3
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
239000007995 HEPES buffer Substances 0.000 description 3
241001494479 Pecora Species 0.000 description 3
108010088847 Peptide YY Proteins 0.000 description 3
102100029909 Peptide YY Human genes 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
241000282887 Suidae Species 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
125000003118 aryl group Chemical group 0.000 description 3
239000001110 calcium chloride Substances 0.000 description 3
235000011148 calcium chloride Nutrition 0.000 description 3
229910001628 calcium chloride Inorganic materials 0.000 description 3
239000001506 calcium phosphate Substances 0.000 description 3
229910000389 calcium phosphate Inorganic materials 0.000 description 3
235000011010 calcium phosphates Nutrition 0.000 description 3
239000000969 carrier Substances 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
206010061428 decreased appetite Diseases 0.000 description 3
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 3
239000002270 dispersing agent Substances 0.000 description 3
239000003651 drinking water Substances 0.000 description 3
235000020188 drinking water Nutrition 0.000 description 3
235000013355 food flavoring agent Nutrition 0.000 description 3
210000001035 gastrointestinal tract Anatomy 0.000 description 3
230000001965 increasing effect Effects 0.000 description 3
239000007788 liquid Substances 0.000 description 3
229940057995 liquid paraffin Drugs 0.000 description 3
229910001629 magnesium chloride Inorganic materials 0.000 description 3
238000004519 manufacturing process Methods 0.000 description 3
239000003921 oil Substances 0.000 description 3
235000019198 oils Nutrition 0.000 description 3
239000004006 olive oil Substances 0.000 description 3
235000008390 olive oil Nutrition 0.000 description 3
229910052760 oxygen Inorganic materials 0.000 description 3
244000144977 poultry Species 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
230000004044 response Effects 0.000 description 3
239000007787 solid Substances 0.000 description 3
239000002904 solvent Substances 0.000 description 3
238000010561 standard procedure Methods 0.000 description 3
230000000638 stimulation Effects 0.000 description 3
125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 3
229910052717 sulfur Inorganic materials 0.000 description 3
239000013589 supplement Substances 0.000 description 3
239000000375 suspending agent Substances 0.000 description 3
229940124597 therapeutic agent Drugs 0.000 description 3
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 3
239000000080 wetting agent Substances 0.000 description 3
PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
HZUBQZOSSIBAFP-OAHLLOKOSA-N (3r)-n,n-dimethyl-1-(2-methyl-6-phenyl-5h-pyrrolo[3,2-d]pyrimidin-4-yl)pyrrolidin-3-amine Chemical compound C1[C@H](N(C)C)CCN1C1=NC(C)=NC2=C1NC(C=1C=CC=CC=1)=C2 HZUBQZOSSIBAFP-OAHLLOKOSA-N 0.000 description 2
125000006663 (C1-C6) perfluoroalkyl group Chemical group 0.000 description 2
125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 description 2
HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 2
VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 2
SJOOTYROPWOHLH-UHFFFAOYSA-N 2-(1H-imidazol-2-yl)-5-methyl-7-pyrrolidin-1-yl-1H-imidazo[4,5-b]pyridine Chemical compound C=12N=C(C=3NC=CN=3)NC2=NC(C)=CC=1N1CCCC1 SJOOTYROPWOHLH-UHFFFAOYSA-N 0.000 description 2
ZKPWMKDTOFLIIW-UHFFFAOYSA-N 2-(2,4-dimethoxyphenyl)-7-methoxy-5-methyl-1h-imidazo[4,5-b]pyridine Chemical compound COC1=CC(OC)=CC=C1C1=NC2=C(OC)C=C(C)N=C2N1 ZKPWMKDTOFLIIW-UHFFFAOYSA-N 0.000 description 2
KAARVEBGIBILBH-UHFFFAOYSA-N 2-(4-fluorophenyl)-5-methyl-7-piperidin-1-yl-1h-imidazo[4,5-b]pyridine Chemical compound C=12N=C(C=3C=CC(F)=CC=3)NC2=NC(C)=CC=1N1CCCCC1 KAARVEBGIBILBH-UHFFFAOYSA-N 0.000 description 2
KUWPETDUKCRCHF-UHFFFAOYSA-N 2-(5-methyl-7-pyrrolidin-1-yl-1h-imidazo[4,5-b]pyridin-2-yl)-1,3-thiazole Chemical compound C=12N=C(C=3SC=CN=3)NC2=NC(C)=CC=1N1CCCC1 KUWPETDUKCRCHF-UHFFFAOYSA-N 0.000 description 2
IZHVBANLECCAGF-UHFFFAOYSA-N 2-hydroxy-3-(octadecanoyloxy)propyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)COC(=O)CCCCCCCCCCCCCCCCC IZHVBANLECCAGF-UHFFFAOYSA-N 0.000 description 2
ZFNVUGRITTVRBZ-UHFFFAOYSA-N 2-methyl-6-phenyl-4-(4-piperidin-1-ylpiperidin-1-yl)-5h-pyrrolo[3,2-d]pyrimidine Chemical group C=12NC(C=3C=CC=CC=3)=CC2=NC(C)=NC=1N(CC1)CCC1N1CCCCC1 ZFNVUGRITTVRBZ-UHFFFAOYSA-N 0.000 description 2
HQPKSLLHTRGJRK-SFHVURJKSA-N 2-methyl-6-phenyl-4-[(2s)-2-(pyrrolidin-1-ylmethyl)pyrrolidin-1-yl]-5h-pyrrolo[3,2-d]pyrimidine Chemical compound C([C@@H]1CCCN1C=1N=C(N=C2C=C(NC2=1)C=1C=CC=CC=1)C)N1CCCC1 HQPKSLLHTRGJRK-SFHVURJKSA-N 0.000 description 2
KZXLMNUUUNIERH-UHFFFAOYSA-N 2-methyl-6-phenyl-4-[2-(2-pyrrolidin-1-ylethyl)piperidin-1-yl]-5h-pyrrolo[3,2-d]pyrimidine Chemical compound C=12NC(C=3C=CC=CC=3)=CC2=NC(C)=NC=1N1CCCCC1CCN1CCCC1 KZXLMNUUUNIERH-UHFFFAOYSA-N 0.000 description 2
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 2
MJAVQMFBCUNOTO-OAHLLOKOSA-N 4-[(2r)-2-(methoxymethyl)pyrrolidin-1-yl]-2-methyl-6-phenyl-5h-pyrrolo[3,2-d]pyrimidine Chemical compound COC[C@H]1CCCN1C1=NC(C)=NC2=C1NC(C=1C=CC=CC=1)=C2 MJAVQMFBCUNOTO-OAHLLOKOSA-N 0.000 description 2
MJAVQMFBCUNOTO-HNNXBMFYSA-N 4-[(2s)-2-(methoxymethyl)pyrrolidin-1-yl]-2-methyl-6-phenyl-5h-pyrrolo[3,2-d]pyrimidine Chemical compound COC[C@@H]1CCCN1C1=NC(C)=NC2=C1NC(C=1C=CC=CC=1)=C2 MJAVQMFBCUNOTO-HNNXBMFYSA-N 0.000 description 2
JDFSAPJOZDZPER-UHFFFAOYSA-N 5-methyl-2-phenyl-7-piperidin-1-yl-1h-imidazo[4,5-b]pyridine Chemical compound C=12NC(C=3C=CC=CC=3)=NC2=NC(C)=CC=1N1CCCCC1 JDFSAPJOZDZPER-UHFFFAOYSA-N 0.000 description 2
AFSASUBGQSIZQV-UHFFFAOYSA-N 5-methyl-2-phenyl-7-pyrrolidin-1-yl-1h-imidazo[4,5-b]pyridine Chemical compound C=12NC(C=3C=CC=CC=3)=NC2=NC(C)=CC=1N1CCCC1 AFSASUBGQSIZQV-UHFFFAOYSA-N 0.000 description 2
NQUMTQBVLYVMBA-UHFFFAOYSA-N 5-methyl-2-pyridin-2-yl-7-pyrrolidin-1-yl-1h-imidazo[4,5-b]pyridine Chemical compound C=12N=C(C=3N=CC=CC=3)NC2=NC(C)=CC=1N1CCCC1 NQUMTQBVLYVMBA-UHFFFAOYSA-N 0.000 description 2
XJIGLBVENJTGNJ-UHFFFAOYSA-N 5-methyl-2-pyridin-3-yl-7-pyrrolidin-1-yl-1h-imidazo[4,5-b]pyridine Chemical compound C=12N=C(C=3C=NC=CC=3)NC2=NC(C)=CC=1N1CCCC1 XJIGLBVENJTGNJ-UHFFFAOYSA-N 0.000 description 2
CAOFAGFDFPOSOD-UHFFFAOYSA-N 5-methyl-2-pyridin-4-yl-7-pyrrolidin-1-yl-1h-imidazo[4,5-b]pyridine Chemical compound C=12N=C(C=3C=CN=CC=3)NC2=NC(C)=CC=1N1CCCC1 CAOFAGFDFPOSOD-UHFFFAOYSA-N 0.000 description 2
ZISYEOXWVPMGEC-UHFFFAOYSA-N 6-methyl-4-pyrrolidin-1-ylpyridine-2,3-diamine Chemical compound NC1=NC(C)=CC(N2CCCC2)=C1N ZISYEOXWVPMGEC-UHFFFAOYSA-N 0.000 description 2
MEMIYCMDGGLSDO-UHFFFAOYSA-N 7-methoxy-5-methyl-2-phenyl-1h-imidazo[4,5-b]pyridine Chemical compound N=1C=2C(OC)=CC(C)=NC=2NC=1C1=CC=CC=C1 MEMIYCMDGGLSDO-UHFFFAOYSA-N 0.000 description 2
244000215068 Acacia senegal Species 0.000 description 2
235000006491 Acacia senegal Nutrition 0.000 description 2
206010002383 Angina Pectoris Diseases 0.000 description 2
208000019901 Anxiety disease Diseases 0.000 description 2
235000003911 Arachis Nutrition 0.000 description 2
244000105624 Arachis hypogaea Species 0.000 description 2
241000416162 Astragalus gummifer Species 0.000 description 2
206010006482 Bronchospasm Diseases 0.000 description 2
125000000882 C2-C6 alkenyl group Chemical group 0.000 description 2
125000003601 C2-C6 alkynyl group Chemical group 0.000 description 2
RUZUQDGMGCSEGR-UHFFFAOYSA-N CC(C)Nc1nc(C)[nH]c2cc(nc12)-c1ccccc1 Chemical compound CC(C)Nc1nc(C)[nH]c2cc(nc12)-c1ccccc1 RUZUQDGMGCSEGR-UHFFFAOYSA-N 0.000 description 2
206010007572 Cardiac hypertrophy Diseases 0.000 description 2
208000006029 Cardiomegaly Diseases 0.000 description 2
208000018152 Cerebral disease Diseases 0.000 description 2
206010008111 Cerebral haemorrhage Diseases 0.000 description 2
208000011231 Crohn disease Diseases 0.000 description 2
108010051696 Growth Hormone Proteins 0.000 description 2
229920000084 Gum arabic Polymers 0.000 description 2
206010019280 Heart failures Diseases 0.000 description 2
101500025005 Homo sapiens Neuropeptide Y Proteins 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
102000004877 Insulin Human genes 0.000 description 2
108090001061 Insulin Proteins 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
101150027439 NPY1 gene Proteins 0.000 description 2
102000009497 Neuropeptide Y1 receptors Human genes 0.000 description 2
108050000303 Neuropeptide Y1 receptors Proteins 0.000 description 2
229910019142 PO4 Inorganic materials 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
229920001774 Perfluoroether Polymers 0.000 description 2
208000018262 Peripheral vascular disease Diseases 0.000 description 2
239000004743 Polypropylene Substances 0.000 description 2
102100024819 Prolactin Human genes 0.000 description 2
108010057464 Prolactin Proteins 0.000 description 2
208000001647 Renal Insufficiency Diseases 0.000 description 2
201000001880 Sexual dysfunction Diseases 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
102100038803 Somatotropin Human genes 0.000 description 2
229920002472 Starch Polymers 0.000 description 2
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
229930006000 Sucrose Natural products 0.000 description 2
206010049418 Sudden Cardiac Death Diseases 0.000 description 2
229920001615 Tragacanth Polymers 0.000 description 2
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
206010046543 Urinary incontinence Diseases 0.000 description 2
206010047139 Vasoconstriction Diseases 0.000 description 2
206010047163 Vasospasm Diseases 0.000 description 2
238000010521 absorption reaction Methods 0.000 description 2
235000010489 acacia gum Nutrition 0.000 description 2
210000000577 adipose tissue Anatomy 0.000 description 2
125000002723 alicyclic group Chemical group 0.000 description 2
125000003342 alkenyl group Chemical group 0.000 description 2
125000000304 alkynyl group Chemical group 0.000 description 2
208000022531 anorexia Diseases 0.000 description 2
230000036506 anxiety Effects 0.000 description 2
206010003119 arrhythmia Diseases 0.000 description 2
230000006793 arrhythmia Effects 0.000 description 2
235000010323 ascorbic acid Nutrition 0.000 description 2
239000011668 ascorbic acid Substances 0.000 description 2
125000004429 atom Chemical group 0.000 description 2
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
102000012740 beta Adrenergic Receptors Human genes 0.000 description 2
108010079452 beta Adrenergic Receptors Proteins 0.000 description 2
210000004204 blood vessel Anatomy 0.000 description 2
229940098773 bovine serum albumin Drugs 0.000 description 2
230000007885 bronchoconstriction Effects 0.000 description 2
244000309464 bull Species 0.000 description 2
229910000019 calcium carbonate Inorganic materials 0.000 description 2
235000010216 calcium carbonate Nutrition 0.000 description 2
235000013339 cereals Nutrition 0.000 description 2
206010008118 cerebral infarction Diseases 0.000 description 2
208000026106 cerebrovascular disease Diseases 0.000 description 2
210000004351 coronary vessel Anatomy 0.000 description 2
235000012343 cottonseed oil Nutrition 0.000 description 2
239000002385 cottonseed oil Substances 0.000 description 2
KVFDZFBHBWTVID-UHFFFAOYSA-N cyclohexanecarbaldehyde Chemical compound O=CC1CCCCC1 KVFDZFBHBWTVID-UHFFFAOYSA-N 0.000 description 2
235000005911 diet Nutrition 0.000 description 2
230000037213 diet Effects 0.000 description 2
208000035475 disorder Diseases 0.000 description 2
238000009826 distribution Methods 0.000 description 2
231100000673 dose–response relationship Toxicity 0.000 description 2
239000000839 emulsion Substances 0.000 description 2
206010015037 epilepsy Diseases 0.000 description 2
239000003925 fat Substances 0.000 description 2
235000019197 fats Nutrition 0.000 description 2
235000013312 flour Nutrition 0.000 description 2
239000012530 fluid Substances 0.000 description 2
230000005176 gastrointestinal motility Effects 0.000 description 2
239000007903 gelatin capsule Substances 0.000 description 2
239000008187 granular material Substances 0.000 description 2
239000000122 growth hormone Substances 0.000 description 2
210000002216 heart Anatomy 0.000 description 2
125000000623 heterocyclic group Chemical group 0.000 description 2
BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
FBPFZTCFMRRESA-UHFFFAOYSA-N hexane-1,2,3,4,5,6-hexol Chemical compound OCC(O)C(O)C(O)C(O)CO FBPFZTCFMRRESA-UHFFFAOYSA-N 0.000 description 2
125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 description 2
208000008384 ileus Diseases 0.000 description 2
230000001771 impaired effect Effects 0.000 description 2
238000011534 incubation Methods 0.000 description 2
230000004968 inflammatory condition Effects 0.000 description 2
208000027866 inflammatory disease Diseases 0.000 description 2
229940125396 insulin Drugs 0.000 description 2
208000001286 intracranial vasospasm Diseases 0.000 description 2
201000006370 kidney failure Diseases 0.000 description 2
235000020997 lean meat Nutrition 0.000 description 2
239000000787 lecithin Substances 0.000 description 2
235000010445 lecithin Nutrition 0.000 description 2
229940067606 lecithin Drugs 0.000 description 2
239000012139 lysis buffer Substances 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
239000000463 material Substances 0.000 description 2
239000012528 membrane Substances 0.000 description 2
108020004999 messenger RNA Proteins 0.000 description 2
208000030159 metabolic disease Diseases 0.000 description 2
230000037323 metabolic rate Effects 0.000 description 2
239000002480 mineral oil Substances 0.000 description 2
235000010446 mineral oil Nutrition 0.000 description 2
239000001788 mono and diglycerides of fatty acids Substances 0.000 description 2
125000002757 morpholinyl group Chemical group 0.000 description 2
208000010125 myocardial infarction Diseases 0.000 description 2
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
230000004770 neurodegeneration Effects 0.000 description 2
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
230000009871 nonspecific binding Effects 0.000 description 2
239000000346 nonvolatile oil Substances 0.000 description 2
239000012053 oil suspension Substances 0.000 description 2
238000007911 parenteral administration Methods 0.000 description 2
230000001575 pathological effect Effects 0.000 description 2
239000008188 pellet Substances 0.000 description 2
239000008194 pharmaceutical composition Substances 0.000 description 2
KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
239000010452 phosphate Substances 0.000 description 2
239000002953 phosphate buffered saline Substances 0.000 description 2
125000003386 piperidinyl group Chemical group 0.000 description 2
239000000843 powder Substances 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
239000000651 prodrug Substances 0.000 description 2
229940002612 prodrug Drugs 0.000 description 2
239000000047 product Substances 0.000 description 2
229940097325 prolactin Drugs 0.000 description 2
QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 2
125000006239 protecting group Chemical group 0.000 description 2
102000004169 proteins and genes Human genes 0.000 description 2
108090000623 proteins and genes Proteins 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
210000005227 renal system Anatomy 0.000 description 2
208000017443 reproductive system disease Diseases 0.000 description 2
208000023504 respiratory system disease Diseases 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
201000000980 schizophrenia Diseases 0.000 description 2
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
230000028327 secretion Effects 0.000 description 2
231100000872 sexual dysfunction Toxicity 0.000 description 2
230000035939 shock Effects 0.000 description 2
DAEPDZWVDSPTHF-UHFFFAOYSA-M sodium pyruvate Chemical compound [Na+].CC(=O)C([O-])=O DAEPDZWVDSPTHF-UHFFFAOYSA-M 0.000 description 2
239000003549 soybean oil Substances 0.000 description 2
235000012424 soybean oil Nutrition 0.000 description 2
235000013599 spices Nutrition 0.000 description 2
239000008107 starch Substances 0.000 description 2
235000019698 starch Nutrition 0.000 description 2
239000005720 sucrose Substances 0.000 description 2
208000014221 sudden cardiac arrest Diseases 0.000 description 2
238000001356 surgical procedure Methods 0.000 description 2
230000002889 sympathetic effect Effects 0.000 description 2
239000006188 syrup Substances 0.000 description 2
235000020357 syrup Nutrition 0.000 description 2
230000000476 thermogenic effect Effects 0.000 description 2
125000004001 thioalkyl group Chemical group 0.000 description 2
239000003749 thyromimetic agent Substances 0.000 description 2
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
230000032258 transport Effects 0.000 description 2
230000025033 vasoconstriction Effects 0.000 description 2
235000015112 vegetable and seed oil Nutrition 0.000 description 2
239000008158 vegetable oil Substances 0.000 description 2
JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 1
GHOKWGTUZJEAQD-ZETCQYMHSA-N (D)-(+)-Pantothenic acid Chemical compound OCC(C)(C)[C@@H](O)C(=O)NCCC(O)=O GHOKWGTUZJEAQD-ZETCQYMHSA-N 0.000 description 1
WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
ZORQXIQZAOLNGE-UHFFFAOYSA-N 1,1-difluorocyclohexane Chemical compound FC1(F)CCCCC1 ZORQXIQZAOLNGE-UHFFFAOYSA-N 0.000 description 1
BEICGJJOZYWQRH-UHFFFAOYSA-N 1-(2-methyl-6-phenyl-5h-pyrrolo[3,2-d]pyrimidin-4-yl)-3,4,4a,5,6,7,8,8a-octahydro-2h-quinoline Chemical compound C=1C2=NC(C)=NC(N3C4CCCCC4CCC3)=C2NC=1C1=CC=CC=C1 BEICGJJOZYWQRH-UHFFFAOYSA-N 0.000 description 1
IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
GZJZZQHTBTUBEL-HNNXBMFYSA-N 2-[4-[2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]ethoxy]phenyl]acetic acid Chemical group C1=NC(N)=CC=C1[C@@H](O)CNCCOC1=CC=C(CC(O)=O)C=C1 GZJZZQHTBTUBEL-HNNXBMFYSA-N 0.000 description 1
QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 1
YGCIOPVWMYGYAJ-UHFFFAOYSA-N 2-chloro-6-methyl-3-nitro-4-pyrrolidin-1-ylpyridine Chemical compound ClC1=NC(C)=CC(N2CCCC2)=C1[N+]([O-])=O YGCIOPVWMYGYAJ-UHFFFAOYSA-N 0.000 description 1
DFEUFTSTPGIVNG-UHFFFAOYSA-N 2-cyclohexyl-5-methyl-7-pyrrolidin-1-yl-1h-imidazo[4,5-b]pyridine Chemical compound C=12N=C(C3CCCCC3)NC2=NC(C)=CC=1N1CCCC1 DFEUFTSTPGIVNG-UHFFFAOYSA-N 0.000 description 1
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-M 3-carboxy-2,3-dihydroxypropanoate Chemical compound OC(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-M 0.000 description 1
VUPUFJJKPBOWEJ-UHFFFAOYSA-N 4-chloro-2-methyl-6-phenyl-5h-pyrrolo[3,2-d]pyrimidine Chemical compound C=1C2=NC(C)=NC(Cl)=C2NC=1C1=CC=CC=C1 VUPUFJJKPBOWEJ-UHFFFAOYSA-N 0.000 description 1
KBZWXACXYVLANW-UHFFFAOYSA-N 6-methyl-2-phenyl-4-pyrrolidin-1-yl-1h-imidazo[4,5-c]pyridine Chemical compound N=1C(C)=CC=2NC(C=3C=CC=CC=3)=NC=2C=1N1CCCC1 KBZWXACXYVLANW-UHFFFAOYSA-N 0.000 description 1
QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
239000005995 Aluminium silicate Substances 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
241000269350 Anura Species 0.000 description 1
108010001478 Bacitracin Proteins 0.000 description 1
208000032841 Bulimia Diseases 0.000 description 1
206010006550 Bulimia nervosa Diseases 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
241000282472 Canis lupus familiaris Species 0.000 description 1
208000024172 Cardiovascular disease Diseases 0.000 description 1
KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
244000060011 Cocos nucifera Species 0.000 description 1
235000013162 Cocos nucifera Nutrition 0.000 description 1
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
DSLZVSRJTYRBFB-LLEIAEIESA-N D-glucaric acid Chemical compound OC(=O)[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O DSLZVSRJTYRBFB-LLEIAEIESA-N 0.000 description 1
FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
RGHNJXZEOKUKBD-SQOUGZDYSA-M D-gluconate Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O RGHNJXZEOKUKBD-SQOUGZDYSA-M 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
208000030814 Eating disease Diseases 0.000 description 1
208000019454 Feeding and Eating disease Diseases 0.000 description 1
241000282326 Felis catus Species 0.000 description 1
BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
102100033063 G protein-activated inward rectifier potassium channel 1 Human genes 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
244000068988 Glycine max Species 0.000 description 1
235000010469 Glycine max Nutrition 0.000 description 1
241000282412 Homo Species 0.000 description 1
101000944266 Homo sapiens G protein-activated inward rectifier potassium channel 1 Proteins 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
ZDXPYRJPNDTMRX-VKHMYHEASA-N L-glutamine Chemical compound OC(=O)[C@@H](N)CCC(N)=O ZDXPYRJPNDTMRX-VKHMYHEASA-N 0.000 description 1
229930182816 L-glutamine Natural products 0.000 description 1
JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
240000007472 Leucaena leucocephala Species 0.000 description 1
235000010643 Leucaena leucocephala Nutrition 0.000 description 1
GDBQQVLCIARPGH-UHFFFAOYSA-N Leupeptin Natural products CC(C)CC(NC(C)=O)C(=O)NC(CC(C)C)C(=O)NC(C=O)CCCN=C(N)N GDBQQVLCIARPGH-UHFFFAOYSA-N 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
241000124008 Mammalia Species 0.000 description 1
240000004658 Medicago sativa Species 0.000 description 1
235000017587 Medicago sativa ssp. sativa Nutrition 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
206010028347 Muscle twitching Diseases 0.000 description 1
229910002651 NO3 Inorganic materials 0.000 description 1
108050002826 Neuropeptide Y Receptor Proteins 0.000 description 1
102000012301 Neuropeptide Y receptor Human genes 0.000 description 1
102000028517 Neuropeptide receptor Human genes 0.000 description 1
108070000018 Neuropeptide receptor Proteins 0.000 description 1
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
239000005642 Oleic acid Substances 0.000 description 1
ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
235000019483 Peanut oil Nutrition 0.000 description 1
102000007079 Peptide Fragments Human genes 0.000 description 1
108010033276 Peptide Fragments Proteins 0.000 description 1
229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
239000004698 Polyethylene Substances 0.000 description 1
229920002873 Polyethylenimine Polymers 0.000 description 1
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
235000019764 Soybean Meal Nutrition 0.000 description 1
235000021355 Stearic acid Nutrition 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
229920004890 Triton X-100 Polymers 0.000 description 1
239000013504 Triton X-100 Substances 0.000 description 1
241000269370 Xenopus <genus> Species 0.000 description 1
240000008042 Zea mays Species 0.000 description 1
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
235000002017 Zea mays subsp mays Nutrition 0.000 description 1
WERKSKAQRVDLDW-ANOHMWSOSA-N [(2s,3r,4r,5r)-2,3,4,5,6-pentahydroxyhexyl] (z)-octadec-9-enoate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO WERKSKAQRVDLDW-ANOHMWSOSA-N 0.000 description 1
229940022663 acetate Drugs 0.000 description 1
DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
102000030621 adenylate cyclase Human genes 0.000 description 1
108060000200 adenylate cyclase Proteins 0.000 description 1
239000002671 adjuvant Substances 0.000 description 1
235000010443 alginic acid Nutrition 0.000 description 1
239000000783 alginic acid Substances 0.000 description 1
229920000615 alginic acid Polymers 0.000 description 1
229960001126 alginic acid Drugs 0.000 description 1
150000004781 alginic acids Chemical class 0.000 description 1
125000002947 alkylene group Chemical group 0.000 description 1
235000012211 aluminium silicate Nutrition 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
150000001450 anions Chemical class 0.000 description 1
239000005557 antagonist Substances 0.000 description 1
230000000844 anti-bacterial effect Effects 0.000 description 1
239000000883 anti-obesity agent Substances 0.000 description 1
230000000259 anti-tumor effect Effects 0.000 description 1
229940125710 antiobesity agent Drugs 0.000 description 1
239000003963 antioxidant agent Substances 0.000 description 1
230000003078 antioxidant effect Effects 0.000 description 1
235000006708 antioxidants Nutrition 0.000 description 1
235000019789 appetite Nutrition 0.000 description 1
230000036528 appetite Effects 0.000 description 1
230000004596 appetite loss Effects 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
125000002029 aromatic hydrocarbon group Chemical group 0.000 description 1
229940072107 ascorbate Drugs 0.000 description 1
229960005070 ascorbic acid Drugs 0.000 description 1
238000003556 assay Methods 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
229960003071 bacitracin Drugs 0.000 description 1
229930184125 bacitracin Natural products 0.000 description 1
CLKOFPXJLQSYAH-ABRJDSQDSA-N bacitracin A Chemical compound C1SC([C@@H](N)[C@@H](C)CC)=N[C@@H]1C(=O)N[C@@H](CC(C)C)C(=O)N[C@H](CCC(O)=O)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H]1C(=O)N[C@H](CCCN)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CC=2N=CNC=2)C(=O)N[C@H](CC(O)=O)C(=O)N[C@@H](CC(N)=O)C(=O)NCCCC1 CLKOFPXJLQSYAH-ABRJDSQDSA-N 0.000 description 1
235000013871 bee wax Nutrition 0.000 description 1
239000012166 beeswax Substances 0.000 description 1
230000006399 behavior Effects 0.000 description 1
SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
229940077388 benzenesulfonate Drugs 0.000 description 1
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
150000003939 benzylamines Chemical class 0.000 description 1
102000016966 beta-2 Adrenergic Receptors Human genes 0.000 description 1
108010014499 beta-2 Adrenergic Receptors Proteins 0.000 description 1
125000002618 bicyclic heterocycle group Chemical group 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
230000004071 biological effect Effects 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-M bisulphate group Chemical group S([O-])(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
230000000740 bleeding effect Effects 0.000 description 1
230000036772 blood pressure Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
239000002374 bone meal Substances 0.000 description 1
229940036811 bone meal Drugs 0.000 description 1
210000004556 brain Anatomy 0.000 description 1
239000006172 buffering agent Substances 0.000 description 1
235000014121 butter Nutrition 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
239000004202 carbamide Substances 0.000 description 1
235000013877 carbamide Nutrition 0.000 description 1
239000001768 carboxy methyl cellulose Substances 0.000 description 1
230000000747 cardiac effect Effects 0.000 description 1
239000012876 carrier material Substances 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
210000003169 central nervous system Anatomy 0.000 description 1
208000015114 central nervous system disease Diseases 0.000 description 1
230000002490 cerebral effect Effects 0.000 description 1
229960000541 cetyl alcohol Drugs 0.000 description 1
239000012320 chlorinating reagent Substances 0.000 description 1
229940001468 citrate Drugs 0.000 description 1
229960004106 citric acid Drugs 0.000 description 1
239000003240 coconut oil Substances 0.000 description 1
235000019864 coconut oil Nutrition 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
235000005822 corn Nutrition 0.000 description 1
235000005687 corn oil Nutrition 0.000 description 1
239000002285 corn oil Substances 0.000 description 1
230000001186 cumulative effect Effects 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
230000007812 deficiency Effects 0.000 description 1
235000014632 disordered eating Nutrition 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
239000000890 drug combination Substances 0.000 description 1
230000020595 eating behavior Effects 0.000 description 1
239000003974 emollient agent Substances 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
238000005516 engineering process Methods 0.000 description 1
CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 1
239000002024 ethyl acetate extract Substances 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
230000000763 evoking effect Effects 0.000 description 1
230000029142 excretion Effects 0.000 description 1
239000000284 extract Substances 0.000 description 1
239000012091 fetal bovine serum Substances 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
230000037406 food intake Effects 0.000 description 1
235000012631 food intake Nutrition 0.000 description 1
238000011990 functional testing Methods 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
239000011521 glass Substances 0.000 description 1
229940050410 gluconate Drugs 0.000 description 1
229930195712 glutamate Natural products 0.000 description 1
229940074045 glyceryl distearate Drugs 0.000 description 1
229940075507 glyceryl monostearate Drugs 0.000 description 1
229940093915 gynecological organic acid Drugs 0.000 description 1
239000007902 hard capsule Substances 0.000 description 1
238000003306 harvesting Methods 0.000 description 1
230000036541 health Effects 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 1
239000007943 implant Substances 0.000 description 1
239000003701 inert diluent Substances 0.000 description 1
238000001802 infusion Methods 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
229940102223 injectable solution Drugs 0.000 description 1
229940102213 injectable suspension Drugs 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
238000007918 intramuscular administration Methods 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
230000007794 irritation Effects 0.000 description 1
TWBYWOBDOCUKOW-UHFFFAOYSA-M isonicotinate Chemical compound [O-]C(=O)C1=CC=NC=C1 TWBYWOBDOCUKOW-UHFFFAOYSA-M 0.000 description 1
QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
210000003734 kidney Anatomy 0.000 description 1
229940001447 lactate Drugs 0.000 description 1
239000008101 lactose Substances 0.000 description 1
GDBQQVLCIARPGH-ULQDDVLXSA-N leupeptin Chemical compound CC(C)C[C@H](NC(C)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@H](C=O)CCCN=C(N)N GDBQQVLCIARPGH-ULQDDVLXSA-N 0.000 description 1
108010052968 leupeptin Proteins 0.000 description 1
230000004130 lipolysis Effects 0.000 description 1
239000003589 local anesthetic agent Substances 0.000 description 1
229960005015 local anesthetics Drugs 0.000 description 1
235000021266 loss of appetite Nutrition 0.000 description 1
208000019017 loss of appetite Diseases 0.000 description 1
239000007937 lozenge Substances 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 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
230000007246 mechanism Effects 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
239000011707 mineral Substances 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
235000013379 molasses Nutrition 0.000 description 1
238000012544 monitoring process Methods 0.000 description 1
GRKFYMOEFWSFJW-UHFFFAOYSA-N n-benzyl-6-methyl-3-nitro-4-pyrrolidin-1-ylpyridin-2-amine Chemical compound [O-][N+](=O)C=1C(NCC=2C=CC=CC=2)=NC(C)=CC=1N1CCCC1 GRKFYMOEFWSFJW-UHFFFAOYSA-N 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
229920001206 natural gum Polymers 0.000 description 1
230000003880 negative regulation of appetite Effects 0.000 description 1
BPGXUIVWLQTVLZ-OFGSCBOVSA-N neuropeptide y(npy) 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](CCCN=C(N)N)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCCN=C(N)N)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(O)=O)NC(=O)[C@H](CC=1N=CNC=1)NC(=O)[C@H](CCCN=C(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](CCCN=C(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 BPGXUIVWLQTVLZ-OFGSCBOVSA-N 0.000 description 1
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
231100000344 non-irritating Toxicity 0.000 description 1
235000021590 normal diet Nutrition 0.000 description 1
208000030212 nutrition disease Diseases 0.000 description 1
GYCKQBWUSACYIF-UHFFFAOYSA-N o-hydroxybenzoic acid ethyl ester Natural products CCOC(=O)C1=CC=CC=C1O GYCKQBWUSACYIF-UHFFFAOYSA-N 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229940014662 pantothenate Drugs 0.000 description 1
235000019161 pantothenic acid Nutrition 0.000 description 1
239000011713 pantothenic acid Substances 0.000 description 1
239000012188 paraffin wax Substances 0.000 description 1
239000000312 peanut oil Substances 0.000 description 1
230000002093 peripheral effect Effects 0.000 description 1
210000002856 peripheral neuron Anatomy 0.000 description 1
239000006187 pill Substances 0.000 description 1
125000004193 piperazinyl group Chemical group 0.000 description 1
229920000573 polyethylene Polymers 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229920001155 polypropylene Polymers 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
229940072033 potash Drugs 0.000 description 1
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
235000015320 potassium carbonate Nutrition 0.000 description 1
230000002335 preservative effect Effects 0.000 description 1
230000008569 process Effects 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
150000003222 pyridines Chemical class 0.000 description 1
229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
SSJGXNSABQPEKM-SBUIBGKBSA-N pyy peptide Chemical group C([C@H](N)C(=O)N1CCC[C@H]1C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CCCCN)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C)C(=O)N1[C@@H](CCC1)C(=O)NCC(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](C)C(=O)N[C@@H](CO)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N[C@@H](C)C(=O)N[C@@H](CO)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C(C)C)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(O)=O)C1=CC=C(O)C=C1 SSJGXNSABQPEKM-SBUIBGKBSA-N 0.000 description 1
239000000018 receptor agonist Substances 0.000 description 1
229940044601 receptor agonist Drugs 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
210000000664 rectum Anatomy 0.000 description 1
230000002829 reductive effect Effects 0.000 description 1
238000010992 reflux Methods 0.000 description 1
230000004648 relaxation of smooth muscle Effects 0.000 description 1
CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
229940081974 saccharin Drugs 0.000 description 1
235000019204 saccharin Nutrition 0.000 description 1
239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
229960001860 salicylate Drugs 0.000 description 1
239000013049 sediment Substances 0.000 description 1
210000002966 serum Anatomy 0.000 description 1
239000008159 sesame oil Substances 0.000 description 1
235000011803 sesame oil Nutrition 0.000 description 1
210000002027 skeletal muscle Anatomy 0.000 description 1
238000002791 soaking Methods 0.000 description 1
235000010413 sodium alginate Nutrition 0.000 description 1
239000000661 sodium alginate Substances 0.000 description 1
229940005550 sodium alginate Drugs 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
229940054269 sodium pyruvate Drugs 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000007901 soft capsule Substances 0.000 description 1
239000004550 soluble concentrate Substances 0.000 description 1
239000001593 sorbitan monooleate Substances 0.000 description 1
235000011069 sorbitan monooleate Nutrition 0.000 description 1
229940035049 sorbitan monooleate Drugs 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
239000004455 soybean meal Substances 0.000 description 1
239000007921 spray Substances 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
238000010254 subcutaneous injection Methods 0.000 description 1
239000007929 subcutaneous injection Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
229910021653 sulphate ion Inorganic materials 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
239000000829 suppository Substances 0.000 description 1
230000002459 sustained effect Effects 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000000454 talc Substances 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
238000012360 testing method Methods 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
210000001519 tissue Anatomy 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
150000003626 triacylglycerols Chemical class 0.000 description 1
238000003828 vacuum filtration Methods 0.000 description 1
239000003981 vehicle Substances 0.000 description 1
230000004580 weight loss Effects 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
- 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
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- 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
- A61P5/00—Drugs for disorders of the endocrine system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Engineering & Computer Science (AREA)
Diabetes (AREA)
Pulmonology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Obesity (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Biomedical Technology (AREA)
Child & Adolescent Psychology (AREA)
Hematology (AREA)
Urology & Nephrology (AREA)
Endocrinology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

HR60/054,734A 1997-08-05 1998-08-04 4-AMINOPYRROLE (3,2-d) PYRIMIDINES AS NEUROPEPTIDE Y RECEPTOR ANTAGONISTS HRP980434A2 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US5473497P	1997-08-05	1997-08-05

Publications (1)

Publication Number	Publication Date
HRP980434A2 true HRP980434A2 (en)	1999-04-30

Family

ID=21993163

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
HR60/054,734A HRP980434A2 (en)	1997-08-05	1998-08-04	4-AMINOPYRROLE (3,2-d) PYRIMIDINES AS NEUROPEPTIDE Y RECEPTOR ANTAGONISTS

Country Status (32)

Country	Link
US (1)	US6187778B1 (de)
EP (1)	EP1003744B1 (de)
JP (1)	JP3711238B2 (de)
KR (1)	KR20010022583A (de)
CN (1)	CN1264381A (de)
AP (1)	AP9801312A0 (de)
AT (1)	ATE296825T1 (de)
AU (1)	AU7927498A (de)
BG (1)	BG104107A (de)
BR (1)	BR9811844A (de)
CA (1)	CA2293621C (de)
CO (1)	CO4960634A1 (de)
DE (1)	DE69830409T2 (de)
EA (1)	EA200000098A1 (de)
ES (1)	ES2241146T3 (de)
GT (1)	GT199800114A (de)
HR (1)	HRP980434A2 (de)
HU (1)	HUP0002956A3 (de)
ID (1)	ID24300A (de)
IL (1)	IL133430A0 (de)
IS (1)	IS5294A (de)
MA (1)	MA24629A1 (de)
NO (1)	NO996178L (de)
OA (1)	OA11277A (de)
PA (1)	PA8456601A1 (de)
PE (1)	PE106199A1 (de)
PL (1)	PL338575A1 (de)
SA (1)	SA98190435A (de)
TN (1)	TNSN98148A1 (de)
TR (1)	TR200000333T2 (de)
WO (1)	WO1999007703A1 (de)
ZA (1)	ZA986968B (de)

Families Citing this family (36)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6187777B1 (en)	1998-02-06	2001-02-13	Amgen Inc.	Compounds and methods which modulate feeding behavior and related diseases
YU23602A (sh) *	1999-09-30	2004-09-03	Neurogen Corporation	Amino supstituisani pirazolo /1,5/a/-1,5-pirimidini i pirazolo /1,5-a/-1,3,5-triazini
EP1990343B1 (de) *	1999-12-24	2012-04-04	Aventis Pharma Limited	Azaindole
GB0117396D0 (en)	2001-07-17	2001-09-05	Glaxo Group Ltd	Chemical compounds
GB0308208D0 (en)	2003-04-09	2003-05-14	Glaxo Group Ltd	Chemical compounds
WO2005118588A1 (ja)	2004-06-02	2005-12-15	Takeda Pharmaceutical Company Limited	縮合複素環化合物
WO2006009734A1 (en)	2004-06-17	2006-01-26	Wyeth	Gonadotropin releasing hormone receptor antagonists
WO2006009736A1 (en)	2004-06-17	2006-01-26	Wyeth	Processes for preparing gonadotropin releasing hormone receptor antagonists
US7465726B2 (en) *	2004-08-02	2008-12-16	Osi Pharmaceuticals, Inc.	Substituted pyrrolo[2.3-B]pyridines
MY179032A (en)	2004-10-25	2020-10-26	Cancer Research Tech Ltd	Ortho-condensed pyridine and pyrimidine derivatives (e.g.purines) as protein kinase inhibitors
AU2006209117B2 (en) *	2005-01-28	2009-12-10	Daewoong Pharmaceutical Co., Ltd.	Novel benzoimidazole derivatives and pharmaceutical composition comprising the same
KR20060087386A (ko) *	2005-01-28	2006-08-02	주식회사 대웅제약	신규 벤조이미다졸 유도체 및 이를 함유하는 약제학적조성물
US7534796B2 (en)	2005-02-18	2009-05-19	Wyeth	Imidazo[4,5-b]pyridine antagonists of gonadotropin releasing hormone receptor
US7538113B2 (en)	2005-02-18	2009-05-26	Wyeth	4-substituted imidazo[4,5-c]pyridine antagonists of gonadotropin releasing hormone receptor
US7582634B2 (en)	2005-02-18	2009-09-01	Wyeth	7-substituted imidazo[4,5-c]pyridine antagonists of gonadotropin releasing hormone receptor
WO2006108218A1 (en) *	2005-04-15	2006-10-19	Regenertech Pty Limited	Use of neuropeptide y (npy) and agonists and antagonists thereof for tissue regeneration
US7531542B2 (en)	2005-05-18	2009-05-12	Wyeth	Benzooxazole and benzothiazole antagonists of gonadotropin releasing hormone receptor
US7582636B2 (en)	2005-05-26	2009-09-01	Wyeth	Piperazinylimidazopyridine and piperazinyltriazolopyridine antagonists of Gonadotropin Releasing Hormone receptor
CA2614544C (en) *	2005-07-13	2013-09-10	Banyu Pharmaceutical Co., Ltd.	Heterocycle-substituted benzimidazole derivative
AR057525A1 (es) *	2005-10-03	2007-12-05	Astrazeneca Ab	Compuestos inhibidores selectivos de gsk3 y un proceso para su preparacion
UY29825A1 (es) *	2005-10-03	2007-05-31	Astrazeneca Ab	Derivados sustituidos de 3h-imidazol-(4,5 b (beta))piridina-2-il benzoatos y benzamidas, composiciones farmacéuticas que los contienen y aplicaciones
WO2007067537A1 (en) *	2005-12-07	2007-06-14	Osi Pharmaceuticals, Inc.	Pyrrolopyridine kinase inhibiting compounds
EP1963315B1 (de) *	2005-12-22	2014-10-08	Cancer Research Technology Limited	Enzyminhibitoren
JP2009528989A (ja)	2006-02-17	2009-08-13	ファイザー・リミテッド	Ｔｌｒ７変調剤としての３−デアザプリン誘導体
JP5606734B2 (ja)	2006-04-25	2014-10-15	アステックス、セラピューティックス、リミテッド	医薬化合物
KR101134239B1 (ko)	2006-07-11	2012-04-10	주식회사 대웅제약	신규한 바이아릴 벤조이미다졸 유도체 및 이를 함유하는 약학 조성물
CN101490037B (zh) *	2006-07-11	2013-06-12	大熊制药株式会社	联芳基苯并咪唑衍生物以及包含该衍生物的药物组合物
CL2007002617A1 (es)	2006-09-11	2008-05-16	Sanofi Aventis	Compuestos derivados de pirrolo[2,3-b]pirazin-6-ilo; composicion farmaceutica que comprende a dichos compuestos; y su uso para tratar inflamacion de las articulaciones, artritis reumatoide, tumores, linfoma de las celulas del manto.
WO2008121064A1 (en) *	2007-03-30	2008-10-09	Astrazeneca Ab	New imidazo[4,5-b]pyridine-6-halo-7-aryl/heteroaryl compounds 705
DE102007027800A1 (de)	2007-06-16	2008-12-18	Bayer Healthcare Ag	Substituierte bicyclische Heteroaryl-Verbindungen und ihre Verwendung
BRPI0818533B8 (pt)	2007-10-11	2021-05-25	Astrazeneca Ab	composto, composição farmacêutica, uso de um composto, e, processo para a preparação de um composto
WO2009098715A2 (en)	2008-01-11	2009-08-13	Natco Pharma Limited	Novel pyrazolo [3, 4 -d] pyrimidine derivatives as anti -cancer agents
WO2012131399A1 (en)	2011-04-01	2012-10-04	Astrazeneca Ab	Therapeutic treatment
PT2785349T (pt)	2011-11-30	2019-12-11	Astrazeneca Ab	Tratamento combinado de cancro
AU2013204533B2 (en)	2012-04-17	2017-02-02	Astrazeneca Ab	Crystalline forms
CN113271938A (zh) *	2018-11-30	2021-08-17	林伯士拉克许米公司	Tyk2抑制剂和其用途

Family Cites Families (14)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3274213A (en)	1961-09-05	1966-09-20	Upjohn Co	Alkoxy-substituted 2-phenyl-1-(tertiary-aminoalkoxy)phenyl-3, 4-dihydronaphthalenes
DE2818676A1 (de) *	1978-04-27	1979-11-08	Troponwerke Gmbh & Co Kg	Substituierte 5,6-dimethylpyrrolo 2,3-d pyrimidine, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel
GB9022644D0 (en) *	1990-10-18	1990-11-28	Ici Plc	Heterocyclic compounds
US5877178A (en) *	1991-04-08	1999-03-02	Duquesne University Of The Holy Ghost	Pyrimidine derivatives and methods of making and using these derivatives
US5235053A (en) *	1992-06-22	1993-08-10	Eli Lilly And Company	Process for the synthesis of 4-hydroxy-5-halopyrrold[2,3-d]pyrimidine intermediates
US5284971A (en)	1992-07-16	1994-02-08	Syntex (U.S.A.) Inc.	4-(3-cyclohexyl-4-hydroxy or-methoxy phenylsulfonyl) 3,5 dibromo phenyl acetic thyromimetic cholesterol-lowering agents
EP0580550B1 (de)	1992-07-21	1997-10-22	Novartis AG	Oxamidsäure-Derivate als hypocholesterämische Mittel
DE59500788D1 (de) *	1994-05-03	1997-11-20	Ciba Geigy Ag	Pyrrolopyrimidinderivate mit antiproliferativer Wirkung
JP4145955B2 (ja) *	1994-09-29	2008-09-03	ノバルティスアクチェンゲゼルシャフト	ピロロ〔２，３−ｄ〕ピリミジン及びその使用
US6562862B1 (en)	1994-10-20	2003-05-13	Eli Lilly And Company	Methods of inhibiting physiological conditions associated with an excess of neuropeptide Y
PL321136A1 (en)	1994-11-07	1997-11-24	Pfizer	Some substituted derivatives of bencylamine as a new class of specific ligands of neuropeptide y1
US5644057A (en) *	1995-05-12	1997-07-01	Neurogen Corporation	Deazapurine derivatives; a new class of CRF1 specific ligands
EP0759441A3 (de)	1995-06-30	1999-06-30	Eli Lilly And Company	Verfahren zur Behandlung von mit Neuropeptid Y assozierten Zuständen
EP0871442A1 (de)	1996-01-09	1998-10-21	Eli Lilly And Company	Benzimidzolyl neuropeptidy rezeptor antagonisten

1998
- 1998-07-10 IL IL13343098A patent/IL133430A0/xx unknown
- 1998-07-10 ID IDW20000021A patent/ID24300A/id unknown
- 1998-07-10 US US09/380,901 patent/US6187778B1/en not_active Expired - Fee Related
- 1998-07-10 DE DE69830409T patent/DE69830409T2/de not_active Expired - Fee Related
- 1998-07-10 PL PL98338575A patent/PL338575A1/xx unknown
- 1998-07-10 CA CA002293621A patent/CA2293621C/en not_active Expired - Fee Related
- 1998-07-10 JP JP2000506207A patent/JP3711238B2/ja not_active Expired - Fee Related
- 1998-07-10 EA EA200000098A patent/EA200000098A1/ru unknown
- 1998-07-10 TR TR2000/00333T patent/TR200000333T2/xx unknown
- 1998-07-10 KR KR1020007001174A patent/KR20010022583A/ko not_active Ceased
- 1998-07-10 ES ES98929573T patent/ES2241146T3/es not_active Expired - Lifetime
- 1998-07-10 CN CN98807398A patent/CN1264381A/zh active Pending
- 1998-07-10 HU HU0002956A patent/HUP0002956A3/hu unknown
- 1998-07-10 WO PCT/IB1998/001053 patent/WO1999007703A1/en not_active Ceased
- 1998-07-10 EP EP98929573A patent/EP1003744B1/de not_active Expired - Lifetime
- 1998-07-10 BR BR9811844-7A patent/BR9811844A/pt not_active Application Discontinuation
- 1998-07-10 AT AT98929573T patent/ATE296825T1/de not_active IP Right Cessation
- 1998-07-10 AU AU79274/98A patent/AU7927498A/en not_active Abandoned
- 1998-07-27 GT GT199800114A patent/GT199800114A/es unknown
- 1998-07-30 PE PE1998000678A patent/PE106199A1/es not_active Application Discontinuation
- 1998-07-30 AP APAP/P/1998/001312A patent/AP9801312A0/en unknown
- 1998-08-03 PA PA19988456601A patent/PA8456601A1/es unknown
- 1998-08-04 ZA ZA9806968A patent/ZA986968B/xx unknown
- 1998-08-04 TN TNTNSN98148A patent/TNSN98148A1/fr unknown
- 1998-08-04 MA MA25203A patent/MA24629A1/fr unknown
- 1998-08-04 HR HR60/054,734A patent/HRP980434A2/hr not_active Application Discontinuation
- 1998-08-05 CO CO98044925A patent/CO4960634A1/es unknown
- 1998-08-19 SA SA98190435A patent/SA98190435A/ar unknown
1999
- 1999-12-10 IS IS5294A patent/IS5294A/is unknown
- 1999-12-14 NO NO996178A patent/NO996178L/no not_active Application Discontinuation
2000
- 2000-01-14 OA OA1200000007A patent/OA11277A/en unknown
- 2000-01-26 BG BG104107A patent/BG104107A/bg unknown

Also Published As

Publication number	Publication date
NO996178L (no)	2000-02-14
CN1264381A (zh)	2000-08-23
US6187778B1 (en)	2001-02-13
PE106199A1 (es)	1999-11-02
TR200000333T2 (tr)	2000-05-22
HUP0002956A2 (hu)	2001-08-28
JP3711238B2 (ja)	2005-11-02
DE69830409D1 (de)	2005-07-07
ZA986968B (en)	2000-02-04
BR9811844A (pt)	2000-08-08
JP2001512729A (ja)	2001-08-28
SA98190435A (ar)	2005-12-03
HUP0002956A3 (en)	2002-01-28
WO1999007703A1 (en)	1999-02-18
ATE296825T1 (de)	2005-06-15
CA2293621A1 (en)	1999-02-18
PA8456601A1 (es)	2000-05-24
GT199800114A (es)	2000-01-18
TNSN98148A1 (fr)	2005-03-15
ES2241146T3 (es)	2005-10-16
EP1003744B1 (de)	2005-06-01
CA2293621C (en)	2003-12-30
AU7927498A (en)	1999-03-01
BG104107A (bg)	2000-08-31
IL133430A0 (en)	2001-04-30
PL338575A1 (en)	2000-11-06
EP1003744A1 (de)	2000-05-31
EA200000098A1 (ru)	2000-08-28
MA24629A1 (fr)	1999-04-01
CO4960634A1 (es)	2000-09-25
DE69830409T2 (de)	2006-01-26
IS5294A (is)	1999-12-10
OA11277A (en)	2003-07-29
AP9801312A0 (en)	2000-01-30
KR20010022583A (ko)	2001-03-26
ID24300A (id)	2000-07-13
NO996178D0 (no)	1999-12-14

Legal Events

Date	Code	Title	Description
1998-08-04	AIPI	Request for the grant of a patent on the basis of a substantive examination of a patent application
1999-04-30	A1OB	Publication of a patent application
2000-08-04	ODRP	Renewal fee for the maintenance of a patent	Payment date: 20000804 Year of fee payment: 3
2007-01-19	ODBI	Application refused

Publication	Publication Date	Title
US6187778B1 (en)	2001-02-13	4-aminopyrrole (3, 2-D) pyrimidines as neuropeptide Y receptor antagonists
US6337332B1 (en)	2002-01-08	Neuropeptide Y receptor antagonists
KR100566854B1 (ko)	2006-04-03	5-ｈｔ 수용체 리간드 및 그의 용도
CN1102596C (zh)	2003-03-05	5H－噻唑并[3,2－a]嘧啶衍生物
EA009742B1 (ru)	2008-04-28	Соединения бициклических пиразолила и имидазолила и их применение
AU726676B2 (en)	2000-11-16	4-aminopyrrole (3,2-d) pyrimidines as Neuropeptide Y Receptor Antagonists
JP3717737B2 (ja)	2005-11-16	神経ペプチドｙアンタゴニスト
EP1027891B1 (de)	2004-12-29	Neuropeptid Y Antagonisten
US20020058671A1 (en)	2002-05-16	Neuropeptide Y antagonists
CZ439199A3 (cs)	2000-07-12	4-Aminopyrrol(3^-d)pyrimidiny jako antagonisty receptoru neuropeptidu Y
MXPA99012095A (es)	2000-09-04	4-aminopirrol (3,2-d) pirimidinas como antagonistas del receptor del neuropeptido y
MXPA00001707A (en)	2001-06-26	Amide derivatives useful as neuropeptide y (npy) antagonists