DE69930835T2 - Bicyclische pyridin-und pyrimidinderivate als neuropeptid y rezeptorantagonisten - Google Patents
Bicyclische pyridin-und pyrimidinderivate als neuropeptid y rezeptorantagonisten Download PDFInfo
- Publication number
- DE69930835T2 DE69930835T2 DE69930835T DE69930835T DE69930835T2 DE 69930835 T2 DE69930835 T2 DE 69930835T2 DE 69930835 T DE69930835 T DE 69930835T DE 69930835 T DE69930835 T DE 69930835T DE 69930835 T2 DE69930835 T2 DE 69930835T2
- Authority
- DE
- Germany
- Prior art keywords
- alkyl
- cycloalkyl
- methyl
- pyrimidine
- alkoxy
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
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- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical class C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 title claims description 11
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 title 2
- 239000002660 neuropeptide Y receptor antagonist Substances 0.000 title 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 title 1
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 289
- 239000000203 mixture Substances 0.000 claims abstract description 128
- 208000008589 Obesity Diseases 0.000 claims abstract description 25
- 235000020824 obesity Nutrition 0.000 claims abstract description 25
- 206010012601 diabetes mellitus Diseases 0.000 claims abstract description 18
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 13
- 208000024827 Alzheimer disease Diseases 0.000 claims abstract description 12
- 208000027866 inflammatory disease Diseases 0.000 claims abstract description 9
- 201000011510 cancer Diseases 0.000 claims abstract description 6
- 239000000126 substance Substances 0.000 claims description 219
- -1 -OH Inorganic materials 0.000 claims description 163
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 155
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 146
- 125000001072 heteroaryl group Chemical group 0.000 claims description 115
- 125000003118 aryl group Chemical group 0.000 claims description 114
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 111
- 229910052739 hydrogen Inorganic materials 0.000 claims description 90
- 125000004104 aryloxy group Chemical group 0.000 claims description 83
- 239000001257 hydrogen Substances 0.000 claims description 80
- 125000006704 (C5-C6) cycloalkyl group Chemical group 0.000 claims description 79
- 125000003545 alkoxy group Chemical group 0.000 claims description 75
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 72
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 66
- 125000006526 (C1-C2) alkyl group Chemical group 0.000 claims description 65
- 150000003254 radicals Chemical class 0.000 claims description 60
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 48
- 229910052736 halogen Inorganic materials 0.000 claims description 44
- 150000002367 halogens Chemical class 0.000 claims description 43
- 125000006536 (C1-C2)alkoxy group Chemical group 0.000 claims description 40
- 125000000217 alkyl group Chemical group 0.000 claims description 40
- 125000000623 heterocyclic group Chemical group 0.000 claims description 40
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 38
- 150000003839 salts Chemical class 0.000 claims description 33
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 28
- 125000004432 carbon atom Chemical group C* 0.000 claims description 28
- 125000005843 halogen group Chemical group 0.000 claims description 27
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 26
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 24
- 238000011282 treatment Methods 0.000 claims description 24
- 238000002360 preparation method Methods 0.000 claims description 21
- 229910052799 carbon Inorganic materials 0.000 claims description 19
- 229910052717 sulfur Inorganic materials 0.000 claims description 19
- 239000003814 drug Substances 0.000 claims description 16
- 150000002431 hydrogen Chemical class 0.000 claims description 16
- 229910052760 oxygen Inorganic materials 0.000 claims description 16
- 239000012453 solvate Substances 0.000 claims description 15
- 125000004423 acyloxy group Chemical group 0.000 claims description 14
- 150000002148 esters Chemical class 0.000 claims description 14
- 238000011321 prophylaxis Methods 0.000 claims description 14
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 13
- 125000001153 fluoro group Chemical group F* 0.000 claims description 13
- 125000001424 substituent group Chemical group 0.000 claims description 13
- 150000001204 N-oxides Chemical class 0.000 claims description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- 229920006395 saturated elastomer Polymers 0.000 claims description 12
- KCTZOTUQSGYWLV-UHFFFAOYSA-N N1C=NC=C2N=CC=C21 Chemical compound N1C=NC=C2N=CC=C21 KCTZOTUQSGYWLV-UHFFFAOYSA-N 0.000 claims description 11
- 229940079593 drug Drugs 0.000 claims description 11
- 125000006529 (C3-C6) alkyl group Chemical group 0.000 claims description 10
- 208000011580 syndromic disease Diseases 0.000 claims description 9
- 206010020751 Hypersensitivity Diseases 0.000 claims description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 208000002551 irritable bowel syndrome Diseases 0.000 claims description 8
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 8
- 230000003961 neuronal insult Effects 0.000 claims description 8
- 208000030814 Eating disease Diseases 0.000 claims description 7
- 208000019454 Feeding and Eating disease Diseases 0.000 claims description 7
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 7
- 235000021061 dietary behavior Nutrition 0.000 claims description 7
- 235000014632 disordered eating Nutrition 0.000 claims description 7
- 208000026278 immune system disease Diseases 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims description 7
- 241000725303 Human immunodeficiency virus Species 0.000 claims description 6
- 206010020772 Hypertension Diseases 0.000 claims description 6
- 239000003937 drug carrier Substances 0.000 claims description 6
- 208000014674 injury Diseases 0.000 claims description 6
- 125000002950 monocyclic group Chemical group 0.000 claims description 6
- 125000002757 morpholinyl group Chemical group 0.000 claims description 6
- 230000008733 trauma Effects 0.000 claims description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 5
- 206010010904 Convulsion Diseases 0.000 claims description 5
- 206010012335 Dependence Diseases 0.000 claims description 5
- 206010012735 Diarrhoea Diseases 0.000 claims description 5
- 208000019022 Mood disease Diseases 0.000 claims description 5
- 201000004681 Psoriasis Diseases 0.000 claims description 5
- 208000028017 Psychotic disease Diseases 0.000 claims description 5
- 206010037660 Pyrexia Diseases 0.000 claims description 5
- 208000007271 Substance Withdrawal Syndrome Diseases 0.000 claims description 5
- 125000001246 bromo group Chemical group Br* 0.000 claims description 5
- 125000003386 piperidinyl group Chemical group 0.000 claims description 5
- 125000004076 pyridyl group Chemical group 0.000 claims description 5
- 229910052727 yttrium Inorganic materials 0.000 claims description 5
- 208000020925 Bipolar disease Diseases 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- 206010008874 Chronic Fatigue Syndrome Diseases 0.000 claims description 4
- 208000011231 Crohn disease Diseases 0.000 claims description 4
- 208000001640 Fibromyalgia Diseases 0.000 claims description 4
- 208000018522 Gastrointestinal disease Diseases 0.000 claims description 4
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- 206010019233 Headaches Diseases 0.000 claims description 4
- 208000023105 Huntington disease Diseases 0.000 claims description 4
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- 208000005314 Multi-Infarct Dementia Diseases 0.000 claims description 4
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 claims description 4
- 208000001132 Osteoporosis Diseases 0.000 claims description 4
- 208000002193 Pain Diseases 0.000 claims description 4
- 208000018737 Parkinson disease Diseases 0.000 claims description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 4
- 208000005107 Premature Birth Diseases 0.000 claims description 4
- 206010036590 Premature baby Diseases 0.000 claims description 4
- 206010039966 Senile dementia Diseases 0.000 claims description 4
- 208000005392 Spasm Diseases 0.000 claims description 4
- 208000006011 Stroke Diseases 0.000 claims description 4
- 208000025865 Ulcer Diseases 0.000 claims description 4
- 206010046543 Urinary incontinence Diseases 0.000 claims description 4
- 201000004810 Vascular dementia Diseases 0.000 claims description 4
- 208000026935 allergic disease Diseases 0.000 claims description 4
- 230000007815 allergy Effects 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 4
- 208000022531 anorexia Diseases 0.000 claims description 4
- 230000001142 anti-diarrhea Effects 0.000 claims description 4
- 208000006673 asthma Diseases 0.000 claims description 4
- 208000026725 cyclothymic disease Diseases 0.000 claims description 4
- 206010061428 decreased appetite Diseases 0.000 claims description 4
- 206010015037 epilepsy Diseases 0.000 claims description 4
- 208000029364 generalized anxiety disease Diseases 0.000 claims description 4
- 231100000869 headache Toxicity 0.000 claims description 4
- 230000002008 hemorrhagic effect Effects 0.000 claims description 4
- 229940088597 hormone Drugs 0.000 claims description 4
- 239000005556 hormone Substances 0.000 claims description 4
- 230000009610 hypersensitivity Effects 0.000 claims description 4
- 230000002218 hypoglycaemic effect Effects 0.000 claims description 4
- 208000000509 infertility Diseases 0.000 claims description 4
- 230000036512 infertility Effects 0.000 claims description 4
- 231100000535 infertility Toxicity 0.000 claims description 4
- 230000000302 ischemic effect Effects 0.000 claims description 4
- 208000029766 myalgic encephalomeyelitis/chronic fatigue syndrome Diseases 0.000 claims description 4
- 230000004770 neurodegeneration Effects 0.000 claims description 4
- 208000015122 neurodegenerative disease Diseases 0.000 claims description 4
- 201000008482 osteoarthritis Diseases 0.000 claims description 4
- 230000036407 pain Effects 0.000 claims description 4
- 230000037324 pain perception Effects 0.000 claims description 4
- 208000019899 phobic disease Diseases 0.000 claims description 4
- 208000028173 post-traumatic stress disease Diseases 0.000 claims description 4
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 4
- 208000019116 sleep disease Diseases 0.000 claims description 4
- 210000000278 spinal cord Anatomy 0.000 claims description 4
- 231100000397 ulcer Toxicity 0.000 claims description 4
- 230000009385 viral infection Effects 0.000 claims description 4
- DMGOZCOEMMLYBQ-UHFFFAOYSA-N 2-methyl-6-phenyl-4-pyrrolidin-1-yl-5h-pyrrolo[3,2-d]pyrimidine Chemical compound C=12NC(C=3C=CC=CC=3)=CC2=NC(C)=NC=1N1CCCC1 DMGOZCOEMMLYBQ-UHFFFAOYSA-N 0.000 claims description 3
- 206010006550 Bulimia nervosa Diseases 0.000 claims description 3
- 208000029650 alcohol withdrawal Diseases 0.000 claims description 3
- 150000001721 carbon Chemical group 0.000 claims description 3
- 210000001072 colon Anatomy 0.000 claims description 3
- 231100000318 excitotoxic Toxicity 0.000 claims description 3
- 230000003492 excitotoxic effect Effects 0.000 claims description 3
- 208000003243 intestinal obstruction Diseases 0.000 claims description 3
- 230000002980 postoperative effect Effects 0.000 claims description 3
- 208000024891 symptom Diseases 0.000 claims description 3
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 3
- KLSNEFPIXYMBHH-UHFFFAOYSA-N 1-(2-methyl-6-phenyl-5h-pyrrolo[3,2-d]pyrimidin-4-yl)pyrrolidin-3-ol Chemical compound C=12NC(C=3C=CC=CC=3)=CC2=NC(C)=NC=1N1CCC(O)C1 KLSNEFPIXYMBHH-UHFFFAOYSA-N 0.000 claims description 2
- NRFWKHLSQWNDNN-UHFFFAOYSA-N 2-(2-methyl-6-phenyl-5h-pyrrolo[3,2-d]pyrimidin-4-yl)-1,3-thiazole Chemical compound C=12NC(C=3C=CC=CC=3)=CC2=NC(C)=NC=1C1=NC=CS1 NRFWKHLSQWNDNN-UHFFFAOYSA-N 0.000 claims description 2
- GSZYQNUCJIAZJL-UHFFFAOYSA-N 2-(2-methyl-6-phenylpiperidin-4-yl)thieno[3,2-d]pyrimidine Chemical compound N1C(C)CC(C=2N=C3C=CSC3=CN=2)CC1C1=CC=CC=C1 GSZYQNUCJIAZJL-UHFFFAOYSA-N 0.000 claims description 2
- VJTAHVDANNKYPH-UHFFFAOYSA-N 2-(2-tert-butyl-6-methylpiperidin-4-yl)thieno[3,2-d]pyrimidine Chemical compound C1C(C(C)(C)C)NC(C)CC1C1=NC=C(SC=C2)C2=N1 VJTAHVDANNKYPH-UHFFFAOYSA-N 0.000 claims description 2
- FGISNVXRIOFKCD-UHFFFAOYSA-N 2-(cyclohexen-1-yl)-7-piperidin-1-yl-1h-pyrrolo[3,2-b]pyridine;hydrochloride Chemical compound Cl.C1CCCCN1C1=CC=NC2=C1NC(C=1CCCCC=1)=C2 FGISNVXRIOFKCD-UHFFFAOYSA-N 0.000 claims description 2
- VHLAEBPEAQVKAB-UHFFFAOYSA-N 2-cyclohexyl-7-piperidin-1-yl-1h-pyrrolo[3,2-b]pyridine Chemical compound C1CCCCC1C1=CC2=NC=CC(N3CCCCC3)=C2N1 VHLAEBPEAQVKAB-UHFFFAOYSA-N 0.000 claims description 2
- RNQZOKCAVOJNSG-UHFFFAOYSA-N 2-methyl-4-(2-methylpyrrolidin-1-yl)-6-phenyl-5h-pyrrolo[3,2-d]pyrimidine Chemical compound CC1CCCN1C1=NC(C)=NC2=C1NC(C=1C=CC=CC=1)=C2 RNQZOKCAVOJNSG-UHFFFAOYSA-N 0.000 claims description 2
- WVUPXOVXHJCBCF-UHFFFAOYSA-N 2-methyl-6-phenyl-4-pyridin-3-yl-5h-pyrrolo[3,2-d]pyrimidine Chemical compound C=12NC(C=3C=CC=CC=3)=CC2=NC(C)=NC=1C1=CC=CN=C1 WVUPXOVXHJCBCF-UHFFFAOYSA-N 0.000 claims description 2
- FGVYRZPTQVFCBR-UHFFFAOYSA-N 3-(7-piperidin-1-yl-1h-pyrrolo[3,2-b]pyridin-2-yl)phenol Chemical compound OC1=CC=CC(C=2NC3=C(N4CCCCC4)C=CN=C3C=2)=C1 FGVYRZPTQVFCBR-UHFFFAOYSA-N 0.000 claims description 2
- SZZDYFWEHMPCAS-UHFFFAOYSA-N 7-piperidin-1-yl-2-pyridin-2-yl-1h-pyrrolo[3,2-b]pyridine Chemical compound C1CCCCN1C1=CC=NC2=C1NC(C=1N=CC=CC=1)=C2 SZZDYFWEHMPCAS-UHFFFAOYSA-N 0.000 claims description 2
- IULADUGXHYYHPM-UHFFFAOYSA-N C12(CC3CC(CC(C1)C3)C2)C2CC(CC(N2)C)C2=NC=C3C(N2)=CC=N3 Chemical compound C12(CC3CC(CC(C1)C3)C2)C2CC(CC(N2)C)C2=NC=C3C(N2)=CC=N3 IULADUGXHYYHPM-UHFFFAOYSA-N 0.000 claims description 2
- PYQPLUULKKMMBG-UHFFFAOYSA-N CC(C)C1CC(CC(N1)c1ccccc1)c1ncc2nccc2[nH]1 Chemical compound CC(C)C1CC(CC(N1)c1ccccc1)c1ncc2nccc2[nH]1 PYQPLUULKKMMBG-UHFFFAOYSA-N 0.000 claims description 2
- LZYCUAFYQRCOTJ-UHFFFAOYSA-N CC1CC(C(C)C(N1)c1ccccc1)c1ncc2nccc2[nH]1 Chemical compound CC1CC(C(C)C(N1)c1ccccc1)c1ncc2nccc2[nH]1 LZYCUAFYQRCOTJ-UHFFFAOYSA-N 0.000 claims description 2
- WREYEVOZVIERLR-UHFFFAOYSA-N CC1CC(CC(N1)c1ccc(C)cc1)c1ncc2nccc2[nH]1 Chemical compound CC1CC(CC(N1)c1ccc(C)cc1)c1ncc2nccc2[nH]1 WREYEVOZVIERLR-UHFFFAOYSA-N 0.000 claims description 2
- XONWLXZQAAGYHS-UHFFFAOYSA-N CC1CC(CCN1)c1ncc2nc(cc2[nH]1)-c1cc2ccccc2o1 Chemical compound CC1CC(CCN1)c1ncc2nc(cc2[nH]1)-c1cc2ccccc2o1 XONWLXZQAAGYHS-UHFFFAOYSA-N 0.000 claims description 2
- OFVJIESDXWQLON-UHFFFAOYSA-N CC1CC(CCN1)c1ncc2nc(cc2[nH]1)-c1ccc(O)cc1 Chemical compound CC1CC(CCN1)c1ncc2nc(cc2[nH]1)-c1ccc(O)cc1 OFVJIESDXWQLON-UHFFFAOYSA-N 0.000 claims description 2
- LZXHSVZICNCOLH-UHFFFAOYSA-N CC1CC(CCN1)c1ncc2nc(cc2[nH]1)-c1ccccn1 Chemical compound CC1CC(CCN1)c1ncc2nc(cc2[nH]1)-c1ccccn1 LZXHSVZICNCOLH-UHFFFAOYSA-N 0.000 claims description 2
- CYCBDGVNBNHFLI-UHFFFAOYSA-N CC1CC(CCN1)c1ncc2nc(cc2[nH]1)-c1cnccn1 Chemical compound CC1CC(CCN1)c1ncc2nc(cc2[nH]1)-c1cnccn1 CYCBDGVNBNHFLI-UHFFFAOYSA-N 0.000 claims description 2
- AZVPBYKCBJVWPQ-UHFFFAOYSA-N CC1NC(CC(C1)C1=NC=C2C(N1)=C(C=N2)C)C2=CC=CC=C2 Chemical compound CC1NC(CC(C1)C1=NC=C2C(N1)=C(C=N2)C)C2=CC=CC=C2 AZVPBYKCBJVWPQ-UHFFFAOYSA-N 0.000 claims description 2
- NVLHTSRJGWGBMO-KBPBESRZSA-N C[C@@H]1CN(C[C@H](C1)C)C1=C2C(NC(=N1)C)=CC(=N2)C1=CC=CC=C1 Chemical compound C[C@@H]1CN(C[C@H](C1)C)C1=C2C(NC(=N1)C)=CC(=N2)C1=CC=CC=C1 NVLHTSRJGWGBMO-KBPBESRZSA-N 0.000 claims description 2
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- JCHBULFVQSZRNC-UHFFFAOYSA-N [1-(2-methyl-6-phenyl-5h-pyrrolo[3,2-d]pyrimidin-4-yl)piperidin-3-yl]methanol Chemical compound C=12NC(C=3C=CC=CC=3)=CC2=NC(C)=NC=1N1CCCC(CO)C1 JCHBULFVQSZRNC-UHFFFAOYSA-N 0.000 claims description 2
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- DRPLTFIHCZOFME-UHFFFAOYSA-N n,n-dimethyl-1-[1-(2-methyl-6-phenyl-5h-pyrrolo[3,2-d]pyrimidin-4-yl)piperidin-2-yl]methanamine Chemical compound CN(C)CC1CCCCN1C1=NC(C)=NC2=C1NC(C=1C=CC=CC=1)=C2 DRPLTFIHCZOFME-UHFFFAOYSA-N 0.000 claims description 2
- 210000003625 skull Anatomy 0.000 claims description 2
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- 125000004417 unsaturated alkyl group Chemical group 0.000 claims description 2
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims 4
- 125000004943 pyrimidin-6-yl group Chemical group N1=CN=CC=C1* 0.000 claims 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
- 229930192474 thiophene Natural products 0.000 claims 2
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 claims 1
- LSELFBQZZQRNQO-UHFFFAOYSA-N 14-methyl-10-phenyl-2,9,13,15-tetrazatetracyclo[7.6.1.02,7.012,16]hexadeca-1(15),10,12(16),13-tetraene Chemical compound C=1C(C=23)=NC(C)=NC=2N2CCCCC2CN3C=1C1=CC=CC=C1 LSELFBQZZQRNQO-UHFFFAOYSA-N 0.000 claims 1
- HMWHEASDSOUKNI-UHFFFAOYSA-N 2-(2-methyl-6-phenylpiperidin-4-yl)-1-oxidothieno[3,2-d]pyrimidin-1-ium Chemical compound N1C(C)CC(C=2[N+](=C3C=CSC3=CN=2)[O-])CC1C1=CC=CC=C1 HMWHEASDSOUKNI-UHFFFAOYSA-N 0.000 claims 1
- VQABLVZTEBQHDS-UHFFFAOYSA-N 2-(2-methyl-6-phenylpiperidin-4-yl)furo[3,2-d]pyrimidine Chemical compound N1C(C)CC(C=2N=C3C=COC3=CN=2)CC1C1=CC=CC=C1 VQABLVZTEBQHDS-UHFFFAOYSA-N 0.000 claims 1
- HFIVJEORNLARNN-UHFFFAOYSA-N 2-(4-fluorophenyl)-5-methyl-7-piperidin-1-yl-1h-pyrrolo[3,2-b]pyridine Chemical compound C=12NC(C=3C=CC(F)=CC=3)=CC2=NC(C)=CC=1N1CCCCC1 HFIVJEORNLARNN-UHFFFAOYSA-N 0.000 claims 1
- QXCNPUFYISWMAY-UHFFFAOYSA-N 2-(4-fluorophenyl)-5-methyl-7-piperidin-1-ylfuro[3,2-b]pyridine Chemical compound C=12OC(C=3C=CC(F)=CC=3)=CC2=NC(C)=CC=1N1CCCCC1 QXCNPUFYISWMAY-UHFFFAOYSA-N 0.000 claims 1
- CGTPYVUQAVCXGU-UHFFFAOYSA-N 2-[2-(4-chlorophenyl)-6-methylpiperidin-4-yl]-1-oxidothieno[3,2-d]pyrimidin-1-ium Chemical compound N1C(C)CC(C=2[N+](=C3C=CSC3=CN=2)[O-])CC1C1=CC=C(Cl)C=C1 CGTPYVUQAVCXGU-UHFFFAOYSA-N 0.000 claims 1
- MYLPTZDXJPMVMW-UHFFFAOYSA-N 2-[2-(4-chlorophenyl)-6-methylpiperidin-4-yl]thieno[3,2-d]pyrimidine Chemical compound N1C(C)CC(C=2N=C3C=CSC3=CN=2)CC1C1=CC=C(Cl)C=C1 MYLPTZDXJPMVMW-UHFFFAOYSA-N 0.000 claims 1
- YRYDJESLVLBPRI-UHFFFAOYSA-N 2-[2-(4-fluorophenyl)-6-methylpiperidin-4-yl]thieno[3,2-d]pyrimidine Chemical compound N1C(C)CC(C=2N=C3C=CSC3=CN=2)CC1C1=CC=C(F)C=C1 YRYDJESLVLBPRI-UHFFFAOYSA-N 0.000 claims 1
- KVZDNBWSPOUUHF-UHFFFAOYSA-N 2-methyl-6-phenyl-4-(4-phenylpiperazin-1-yl)-5h-pyrrolo[3,2-d]pyrimidine Chemical compound C=12NC(C=3C=CC=CC=3)=CC2=NC(C)=NC=1N(CC1)CCN1C1=CC=CC=C1 KVZDNBWSPOUUHF-UHFFFAOYSA-N 0.000 claims 1
- BNFLOTVXLMSRMX-UHFFFAOYSA-N 2-phenyl-4-[2-(trifluoromethyl)thiophen-3-yl]piperidine Chemical compound S1C=CC(C2CC(NCC2)C=2C=CC=CC=2)=C1C(F)(F)F BNFLOTVXLMSRMX-UHFFFAOYSA-N 0.000 claims 1
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 1
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Classifications
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Landscapes
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| US09/246,775 US6187777B1 (en) | 1998-02-06 | 1999-02-04 | Compounds and methods which modulate feeding behavior and related diseases |
| PCT/US1999/002500 WO1999040091A1 (en) | 1998-02-06 | 1999-02-05 | Bicyclic pyridine and pyrimidine derivatives as neuropeptide y receptor antagonists |
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| DE69930835D1 DE69930835D1 (de) | 2006-05-24 |
| DE69930835T2 true DE69930835T2 (de) | 2006-10-19 |
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| WO1998010381A1 (en) * | 1996-09-04 | 1998-03-12 | Intertrust Technologies Corp. | Trusted infrastructure support systems, methods and techniques for secure electronic commerce, electronic transactions, commerce process control and automation, distributed computing, and rights management |
| WO1998030231A1 (en) * | 1997-01-07 | 1998-07-16 | Amylin Pharmaceuticals, Inc. | Use of exendins and agonists thereof for the reduction of food intake |
| JP2001522853A (ja) | 1997-11-11 | 2001-11-20 | ファイザー・プロダクツ・インク | 抗癌剤として有用なチエノピリミジンおよびチエノピリジン誘導体 |
| DE69929235T2 (de) | 1998-11-10 | 2006-08-24 | Merck & Co., Inc. | Spiro-indole als y5-rezeptor antagonisten |
| HK1038926B (en) | 1998-11-12 | 2003-07-18 | Neurocrine Biosciences, Inc. | Crf receptor antagonists and methods relating thereto |
| US6531475B1 (en) | 1998-11-12 | 2003-03-11 | Neurocrine Biosciences, Inc. | CRF receptor antagonists and methods relating thereto |
| CA2634299C (en) * | 1999-04-08 | 2011-05-31 | Industrial Research Limited | Process for preparing inhibitors of nucleoside metabolism |
| GB9915437D0 (en) | 1999-07-01 | 1999-09-01 | Cerebrus Ltd | Chemical compounds III |
| EP1214303A1 (en) * | 1999-08-31 | 2002-06-19 | Merck & Co., Inc. | Heterocyclic compounds and methods of use thereof |
| IL148903A0 (en) | 1999-09-30 | 2002-09-12 | Neurogen Corp | Certain alkylene diamine-substituted heterocycles |
| YU23802A (sh) * | 1999-09-30 | 2004-09-03 | Neurogen Corporation | Određeni alkilen diamin-supstituisani pirazolo/1,5-a/-1,5- piramidini i pirazolo/1,5-a/1,3,5-triazini |
| ATE347553T1 (de) * | 1999-09-30 | 2006-12-15 | Neurogen Corp | Amino-substituierte pyrazolo 1,5-aö-1,5- pyrimidine und pyrazolo 1,5-aö-1,3,5-triazine |
| AU2001263288A1 (en) * | 2000-05-18 | 2001-11-26 | Neurocrine Biosciences, Inc. | Crf receptor antagonists |
| US7276492B2 (en) * | 2000-06-01 | 2007-10-02 | Kevorkian Robert C | Use of ACE inhibitors for treatment of patients suffering from behavioral disorders |
| AU9649301A (en) * | 2000-10-03 | 2002-04-15 | Univ California | Use of neuropeptide-y antagonists in treatment of alcoholism |
| US8564661B2 (en) | 2000-10-24 | 2013-10-22 | Objectvideo, Inc. | Video analytic rule detection system and method |
| GB0100620D0 (en) | 2001-01-10 | 2001-02-21 | Vernalis Res Ltd | Chemical cokpounds V |
| US20050226918A1 (en) * | 2001-08-13 | 2005-10-13 | Macdonald Stuart G | Delivery system for insulin and other therapeutic agents |
| US6770652B2 (en) * | 2001-10-18 | 2004-08-03 | Duquesne University Of The Holy Ghost | Multiple acting anti-angiogenic and cytotoxic compounds and methods for using the same |
| ES2193875B2 (es) | 2002-04-09 | 2005-03-01 | Laboratorios Del Dr. Esteve, S.A. | Derivados de benzoxazinona, su preparacion y su aplicacion como medicamentos. |
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| US5644057A (en) * | 1995-05-12 | 1997-07-01 | Neurogen Corporation | Deazapurine derivatives; a new class of CRF1 specific ligands |
| AU716993B2 (en) | 1995-05-12 | 2000-03-16 | Neurogen Corporation | Novel deazapurine derivatives; a new class of CRF1 specific ligands |
| ATE247469T1 (de) | 1995-06-07 | 2003-09-15 | Pfizer | Heterocyclische kondensierte pyrimidin-derivate |
| FR2735777B1 (fr) * | 1995-06-21 | 1997-09-12 | Sanofi Sa | Derives de 4-phenylaminothiazole, leur procede de preparation et les compositions pharmaceutiques les contenant |
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-
1999
- 1999-02-04 US US09/246,775 patent/US6187777B1/en not_active Expired - Fee Related
- 1999-02-05 SI SI9930893T patent/SI1054887T1/sl unknown
- 1999-02-05 PT PT99906756T patent/PT1054887E/pt unknown
- 1999-02-05 AU AU26590/99A patent/AU747920B2/en not_active Ceased
- 1999-02-05 DE DE69930835T patent/DE69930835T2/de not_active Expired - Lifetime
- 1999-02-05 AT AT99906756T patent/ATE323088T1/de not_active IP Right Cessation
- 1999-02-05 JP JP2000530520A patent/JP2003502272A/ja not_active Withdrawn
- 1999-02-05 CA CA002319275A patent/CA2319275C/en not_active Expired - Fee Related
- 1999-02-05 EP EP99906756A patent/EP1054887B1/en not_active Expired - Lifetime
- 1999-02-05 WO PCT/US1999/002500 patent/WO1999040091A1/en not_active Ceased
- 1999-02-05 ES ES99906756T patent/ES2257851T3/es not_active Expired - Lifetime
- 1999-02-05 DK DK99906756T patent/DK1054887T3/da active
-
2000
- 2000-08-16 US US09/640,263 patent/US6583154B1/en not_active Expired - Fee Related
-
2006
- 2006-07-06 CY CY20061100932T patent/CY1105476T1/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP1054887B1 (en) | 2006-04-12 |
| AU2659099A (en) | 1999-08-23 |
| SI1054887T1 (sl) | 2006-08-31 |
| CA2319275A1 (en) | 1999-08-12 |
| CA2319275C (en) | 2007-10-16 |
| PT1054887E (pt) | 2006-06-30 |
| ES2257851T3 (es) | 2006-08-01 |
| JP2003502272A (ja) | 2003-01-21 |
| ATE323088T1 (de) | 2006-04-15 |
| DK1054887T3 (da) | 2006-05-08 |
| DE69930835D1 (de) | 2006-05-24 |
| US6583154B1 (en) | 2003-06-24 |
| EP1054887A1 (en) | 2000-11-29 |
| AU747920B2 (en) | 2002-05-30 |
| US6187777B1 (en) | 2001-02-13 |
| CY1105476T1 (el) | 2010-07-28 |
| WO1999040091A1 (en) | 1999-08-12 |
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