JP2003520272A5 - - Google Patents
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- JP2003520272A5 JP2003520272A5 JP2001553267A JP2001553267A JP2003520272A5 JP 2003520272 A5 JP2003520272 A5 JP 2003520272A5 JP 2001553267 A JP2001553267 A JP 2001553267A JP 2001553267 A JP2001553267 A JP 2001553267A JP 2003520272 A5 JP2003520272 A5 JP 2003520272A5
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- JP
- Japan
- Prior art keywords
- alkyl
- cycloalkyl
- alkylene
- optionally
- cycloalkylene
- 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.)
- Pending
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- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 40
- 125000000217 alkyl group Chemical group 0.000 claims 37
- 150000001875 compounds Chemical class 0.000 claims 26
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 22
- -1 methoxy, ethoxy Chemical group 0.000 claims 20
- 125000004406 C3-C8 cycloalkylene group Chemical group 0.000 claims 19
- 125000001424 substituent group Chemical group 0.000 claims 17
- 125000001153 fluoro group Chemical group F* 0.000 claims 15
- 229910052739 hydrogen Inorganic materials 0.000 claims 14
- 125000003118 aryl group Chemical group 0.000 claims 13
- 239000001257 hydrogen Substances 0.000 claims 13
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 10
- 229910052760 oxygen Inorganic materials 0.000 claims 10
- 239000008194 pharmaceutical composition Substances 0.000 claims 10
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 9
- 150000002431 hydrogen Chemical class 0.000 claims 9
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 8
- 239000001301 oxygen Substances 0.000 claims 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims 7
- 125000005843 halogen group Chemical group 0.000 claims 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 6
- 229910052757 nitrogen Inorganic materials 0.000 claims 6
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 5
- 206010012335 Dependence Diseases 0.000 claims 4
- 206010034912 Phobia Diseases 0.000 claims 4
- 206010047700 Vomiting Diseases 0.000 claims 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
- 208000035475 disorder Diseases 0.000 claims 4
- 230000008673 vomiting Effects 0.000 claims 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 3
- 125000005842 heteroatom Chemical group 0.000 claims 3
- 125000000623 heterocyclic group Chemical group 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 208000019899 phobic disease Diseases 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- 229910052717 sulfur Inorganic materials 0.000 claims 3
- 208000011580 syndromic disease Diseases 0.000 claims 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 2
- XTFIVUDBNACUBN-UHFFFAOYSA-N 1,3,5-trinitro-1,3,5-triazinane Chemical compound [O-][N+](=O)N1CN([N+]([O-])=O)CN([N+]([O-])=O)C1 XTFIVUDBNACUBN-UHFFFAOYSA-N 0.000 claims 2
- 206010007559 Cardiac failure congestive Diseases 0.000 claims 2
- 208000019022 Mood disease Diseases 0.000 claims 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 2
- 206010037660 Pyrexia Diseases 0.000 claims 2
- 102000003141 Tachykinin Human genes 0.000 claims 2
- 229940123445 Tricyclic antidepressant Drugs 0.000 claims 2
- 230000002159 abnormal effect Effects 0.000 claims 2
- 125000002947 alkylene group Chemical group 0.000 claims 2
- 239000005557 antagonist Substances 0.000 claims 2
- 210000004556 brain Anatomy 0.000 claims 2
- 125000001246 bromo group Chemical group Br* 0.000 claims 2
- 230000027288 circadian rhythm Effects 0.000 claims 2
- ZPUCINDJVBIVPJ-LJISPDSOSA-N cocaine Chemical compound O([C@H]1C[C@@H]2CC[C@@H](N2C)[C@H]1C(=O)OC)C(=O)C1=CC=CC=C1 ZPUCINDJVBIVPJ-LJISPDSOSA-N 0.000 claims 2
- 125000002993 cycloalkylene group Chemical group 0.000 claims 2
- 230000003111 delayed effect Effects 0.000 claims 2
- 229940079593 drug Drugs 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 229960003692 gamma aminobutyric acid Drugs 0.000 claims 2
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 claims 2
- 208000026278 immune system disease Diseases 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 2
- 239000000018 receptor agonist Substances 0.000 claims 2
- 229940044601 receptor agonist Drugs 0.000 claims 2
- 229920006395 saturated elastomer Polymers 0.000 claims 2
- 208000019116 sleep disease Diseases 0.000 claims 2
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 2
- 108060008037 tachykinin Proteins 0.000 claims 2
- 239000003029 tricyclic antidepressant agent Substances 0.000 claims 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- QDZOEBFLNHCSSF-PFFBOGFISA-N (2S)-2-[[(2R)-2-[[(2S)-1-[(2S)-6-amino-2-[[(2S)-1-[(2R)-2-amino-5-carbamimidamidopentanoyl]pyrrolidine-2-carbonyl]amino]hexanoyl]pyrrolidine-2-carbonyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]-N-[(2R)-1-[[(2S)-1-[[(2R)-1-[[(2S)-1-[[(2S)-1-amino-4-methyl-1-oxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]pentanediamide Chemical compound C([C@@H](C(=O)N[C@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(N)=O)NC(=O)[C@@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CCCCN)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](N)CCCNC(N)=N)C1=CC=CC=C1 QDZOEBFLNHCSSF-PFFBOGFISA-N 0.000 claims 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims 1
- RTHCYVBBDHJXIQ-MRXNPFEDSA-N (R)-fluoxetine Chemical compound O([C@H](CCNC)C=1C=CC=CC=1)C1=CC=C(C(F)(F)F)C=C1 RTHCYVBBDHJXIQ-MRXNPFEDSA-N 0.000 claims 1
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 claims 1
- CRQCBBCSYKAPDW-UHFFFAOYSA-N 2-(4-bromo-2,6-dimethylphenoxy)-6-methyl-4-(pentan-3-ylamino)pyridine-3-carbonitrile Chemical compound CCC(CC)NC1=CC(C)=NC(OC=2C(=CC(Br)=CC=2C)C)=C1C#N CRQCBBCSYKAPDW-UHFFFAOYSA-N 0.000 claims 1
- DVPXGVDTNQUZJL-UHFFFAOYSA-N 2-(4-bromo-2-methoxyphenoxy)-6-methyl-4-(pentan-3-ylamino)pyridine-3-carbonitrile Chemical compound CCC(CC)NC1=CC(C)=NC(OC=2C(=CC(Br)=CC=2)OC)=C1C#N DVPXGVDTNQUZJL-UHFFFAOYSA-N 0.000 claims 1
- HXHYJQGOWDOAQL-UHFFFAOYSA-N 2-(4-bromo-2-methoxyphenoxy)-6-methyl-4-(pentan-3-ylamino)pyridine-3-carboxamide Chemical compound CCC(CC)NC1=CC(C)=NC(OC=2C(=CC(Br)=CC=2)OC)=C1C(N)=O HXHYJQGOWDOAQL-UHFFFAOYSA-N 0.000 claims 1
- GATYVUUKXLTIJT-UHFFFAOYSA-N 2-(4-chloro-2,6-dimethylphenoxy)-3,6-dimethyl-n-pentan-3-ylpyridin-4-amine Chemical compound CCC(CC)NC1=CC(C)=NC(OC=2C(=CC(Cl)=CC=2C)C)=C1C GATYVUUKXLTIJT-UHFFFAOYSA-N 0.000 claims 1
- PBZWSSIFISEGAS-UHFFFAOYSA-N 2-(4-chloro-2,6-dimethylphenoxy)-4-(1-hydroxybutan-2-ylamino)-n,6-dimethylpyridine-3-carboxamide Chemical compound CCC(CO)NC1=CC(C)=NC(OC=2C(=CC(Cl)=CC=2C)C)=C1C(=O)NC PBZWSSIFISEGAS-UHFFFAOYSA-N 0.000 claims 1
- CWYGPMSXGZKRIP-UHFFFAOYSA-N 2-(4-chloro-2,6-dimethylphenoxy)-4-(1-methoxybutan-2-ylamino)-6-methylpyridine-3-carboxamide Chemical compound COCC(CC)NC1=CC(C)=NC(OC=2C(=CC(Cl)=CC=2C)C)=C1C(N)=O CWYGPMSXGZKRIP-UHFFFAOYSA-N 0.000 claims 1
- NJRJOSPWGJQYIE-UHFFFAOYSA-N 2-(4-chloro-2,6-dimethylphenoxy)-4-(1-methoxybutan-2-ylamino)-n,6-dimethylpyridine-3-carboxamide Chemical compound COCC(CC)NC1=CC(C)=NC(OC=2C(=CC(Cl)=CC=2C)C)=C1C(=O)NC NJRJOSPWGJQYIE-UHFFFAOYSA-N 0.000 claims 1
- BJILKEUBIUCVAS-UHFFFAOYSA-N 2-(4-chloro-2,6-dimethylphenoxy)-4-(2-methoxypentan-3-ylamino)-6-methylpyridine-3-carboxamide Chemical compound COC(C)C(CC)NC1=CC(C)=NC(OC=2C(=CC(Cl)=CC=2C)C)=C1C(N)=O BJILKEUBIUCVAS-UHFFFAOYSA-N 0.000 claims 1
- UFMFUXYHEUAHHY-UHFFFAOYSA-N 2-(4-chloro-2,6-dimethylphenoxy)-4-(2-methoxypentan-3-ylamino)-n,6-dimethylpyridine-3-carboxamide Chemical compound COC(C)C(CC)NC1=CC(C)=NC(OC=2C(=CC(Cl)=CC=2C)C)=C1C(=O)NC UFMFUXYHEUAHHY-UHFFFAOYSA-N 0.000 claims 1
- JLGFGKMKPSXEQE-UHFFFAOYSA-N 2-[4-chloro-2-(trifluoromethoxy)phenoxy]-6-methyl-4-(pentan-3-ylamino)pyridine-3-carboxamide Chemical compound CCC(CC)NC1=CC(C)=NC(OC=2C(=CC(Cl)=CC=2)OC(F)(F)F)=C1C(N)=O JLGFGKMKPSXEQE-UHFFFAOYSA-N 0.000 claims 1
- HPDGHEAXAFGTGP-UHFFFAOYSA-N 2-[4-chloro-2-(trifluoromethoxy)phenoxy]-N,6-dimethyl-4-(pentan-3-ylamino)pyridine-3-carboxamide Chemical compound CCC(CC)NC1=CC(C)=NC(OC=2C(=CC(Cl)=CC=2)OC(F)(F)F)=C1C(=O)NC HPDGHEAXAFGTGP-UHFFFAOYSA-N 0.000 claims 1
- 239000003477 4 aminobutyric acid receptor stimulating agent Substances 0.000 claims 1
- ZPSJLQMQKUVCKZ-UHFFFAOYSA-N 4-(3,6-dimethyl-4-pentan-3-yloxypyridin-2-yl)oxy-3,5-dimethylbenzamide Chemical compound CCC(CC)OC1=CC(C)=NC(OC=2C(=CC(=CC=2C)C(N)=O)C)=C1C ZPSJLQMQKUVCKZ-UHFFFAOYSA-N 0.000 claims 1
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims 1
- 102000056834 5-HT2 Serotonin Receptors Human genes 0.000 claims 1
- 108091005479 5-HT2 receptors Proteins 0.000 claims 1
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims 1
- 206010053164 Alcohol withdrawal syndrome Diseases 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- 208000000103 Anorexia Nervosa Diseases 0.000 claims 1
- 208000019901 Anxiety disease Diseases 0.000 claims 1
- 208000020925 Bipolar disease Diseases 0.000 claims 1
- 241000283690 Bos taurus Species 0.000 claims 1
- 201000006474 Brain Ischemia Diseases 0.000 claims 1
- 206010008120 Cerebral ischaemia Diseases 0.000 claims 1
- 206010008874 Chronic Fatigue Syndrome Diseases 0.000 claims 1
- GDLIGKIOYRNHDA-UHFFFAOYSA-N Clomipramine Chemical compound C1CC2=CC=C(Cl)C=C2N(CCCN(C)C)C2=CC=CC=C21 GDLIGKIOYRNHDA-UHFFFAOYSA-N 0.000 claims 1
- 206010010904 Convulsion Diseases 0.000 claims 1
- 229940122010 Corticotropin releasing factor antagonist Drugs 0.000 claims 1
- 208000011231 Crohn disease Diseases 0.000 claims 1
- 206010012289 Dementia Diseases 0.000 claims 1
- HCYAFALTSJYZDH-UHFFFAOYSA-N Desimpramine Chemical compound C1CC2=CC=CC=C2N(CCCNC)C2=CC=CC=C21 HCYAFALTSJYZDH-UHFFFAOYSA-N 0.000 claims 1
- 206010012735 Diarrhoea Diseases 0.000 claims 1
- 206010013754 Drug withdrawal syndrome Diseases 0.000 claims 1
- 208000030814 Eating disease Diseases 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- 208000019454 Feeding and Eating disease Diseases 0.000 claims 1
- 208000001640 Fibromyalgia Diseases 0.000 claims 1
- 241000287828 Gallus gallus Species 0.000 claims 1
- 206010019196 Head injury Diseases 0.000 claims 1
- 206010019233 Headaches Diseases 0.000 claims 1
- 206010019280 Heart failures Diseases 0.000 claims 1
- GVGLGOZIDCSQPN-PVHGPHFFSA-N Heroin Chemical compound O([C@H]1[C@H](C=C[C@H]23)OC(C)=O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4OC(C)=O GVGLGOZIDCSQPN-PVHGPHFFSA-N 0.000 claims 1
- 241000725303 Human immunodeficiency virus Species 0.000 claims 1
- 206010020751 Hypersensitivity Diseases 0.000 claims 1
- 206010020772 Hypertension Diseases 0.000 claims 1
- 206010061216 Infarction Diseases 0.000 claims 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims 1
- 208000007101 Muscle Cramp Diseases 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- PHVGLTMQBUFIQQ-UHFFFAOYSA-N Nortryptiline Chemical compound C1CC2=CC=CC=C2C(=CCCNC)C2=CC=CC=C21 PHVGLTMQBUFIQQ-UHFFFAOYSA-N 0.000 claims 1
- 208000008589 Obesity Diseases 0.000 claims 1
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 claims 1
- 208000001132 Osteoporosis Diseases 0.000 claims 1
- 208000002193 Pain Diseases 0.000 claims 1
- 241001494479 Pecora Species 0.000 claims 1
- 206010054048 Postoperative ileus Diseases 0.000 claims 1
- 201000009916 Postpartum depression Diseases 0.000 claims 1
- 206010036618 Premenstrual syndrome Diseases 0.000 claims 1
- 102100024304 Protachykinin-1 Human genes 0.000 claims 1
- 201000004681 Psoriasis Diseases 0.000 claims 1
- 208000028017 Psychotic disease Diseases 0.000 claims 1
- 206010041250 Social phobia Diseases 0.000 claims 1
- 208000005392 Spasm Diseases 0.000 claims 1
- 101800003906 Substance P Proteins 0.000 claims 1
- 208000007271 Substance Withdrawal Syndrome Diseases 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- 208000001871 Tachycardia Diseases 0.000 claims 1
- 208000025865 Ulcer Diseases 0.000 claims 1
- 206010046543 Urinary incontinence Diseases 0.000 claims 1
- 102000002852 Vasopressins Human genes 0.000 claims 1
- 108010004977 Vasopressins Proteins 0.000 claims 1
- 208000029650 alcohol withdrawal Diseases 0.000 claims 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 1
- 230000007815 allergy Effects 0.000 claims 1
- 229960000836 amitriptyline Drugs 0.000 claims 1
- KRMDCWKBEZIMAB-UHFFFAOYSA-N amitriptyline Chemical compound C1CC2=CC=CC=C2C(=CCCN(C)C)C2=CC=CC=C21 KRMDCWKBEZIMAB-UHFFFAOYSA-N 0.000 claims 1
- 229960002519 amoxapine Drugs 0.000 claims 1
- QWGDMFLQWFTERH-UHFFFAOYSA-N amoxapine Chemical compound C12=CC(Cl)=CC=C2OC2=CC=CC=C2N=C1N1CCNCC1 QWGDMFLQWFTERH-UHFFFAOYSA-N 0.000 claims 1
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims 1
- 230000003042 antagnostic effect Effects 0.000 claims 1
- KBZOIRJILGZLEJ-LGYYRGKSSA-N argipressin Chemical compound C([C@H]1C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CSSC[C@@H](C(N[C@@H](CC=2C=CC(O)=CC=2)C(=O)N1)=O)N)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCN=C(N)N)C(=O)NCC(N)=O)C1=CC=CC=C1 KBZOIRJILGZLEJ-LGYYRGKSSA-N 0.000 claims 1
- 208000006673 asthma Diseases 0.000 claims 1
- 229940049706 benzodiazepine Drugs 0.000 claims 1
- 125000003310 benzodiazepinyl group Chemical class N1N=C(C=CC2=C1C=CC=C2)* 0.000 claims 1
- SNPPWIUOZRMYNY-UHFFFAOYSA-N bupropion Chemical compound CC(C)(C)NC(C)C(=O)C1=CC=CC(Cl)=C1 SNPPWIUOZRMYNY-UHFFFAOYSA-N 0.000 claims 1
- 229960001058 bupropion Drugs 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 229960000623 carbamazepine Drugs 0.000 claims 1
- FFGPTBGBLSHEPO-UHFFFAOYSA-N carbamazepine Chemical compound C1=CC2=CC=CC=C2N(C(=O)N)C2=CC=CC=C21 FFGPTBGBLSHEPO-UHFFFAOYSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 206010061592 cardiac fibrillation Diseases 0.000 claims 1
- 230000002490 cerebral effect Effects 0.000 claims 1
- 206010008118 cerebral infarction Diseases 0.000 claims 1
- 229960004606 clomipramine Drugs 0.000 claims 1
- 229960003920 cocaine Drugs 0.000 claims 1
- 210000001072 colon Anatomy 0.000 claims 1
- 230000002920 convulsive effect Effects 0.000 claims 1
- 239000002769 corticotropin releasing factor antagonist Substances 0.000 claims 1
- 229960003914 desipramine Drugs 0.000 claims 1
- 229960002069 diamorphine Drugs 0.000 claims 1
- 235000014632 disordered eating Nutrition 0.000 claims 1
- 229960005426 doxepin Drugs 0.000 claims 1
- ODQWQRRAPPTVAG-GZTJUZNOSA-N doxepin Chemical compound C1OC2=CC=CC=C2C(=C/CCN(C)C)/C2=CC=CC=C21 ODQWQRRAPPTVAG-GZTJUZNOSA-N 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 230000004064 dysfunction Effects 0.000 claims 1
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- 150000002148 esters Chemical class 0.000 claims 1
- 230000002600 fibrillogenic effect Effects 0.000 claims 1
- 229960002464 fluoxetine Drugs 0.000 claims 1
- 231100000869 headache Toxicity 0.000 claims 1
- 230000002008 hemorrhagic effect Effects 0.000 claims 1
- 125000001072 heteroaryl group Chemical group 0.000 claims 1
- 230000000971 hippocampal effect Effects 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 229960004801 imipramine Drugs 0.000 claims 1
- BCGWQEUPMDMJNV-UHFFFAOYSA-N imipramine Chemical compound C1CC2=CC=CC=C2N(CCCN(C)C)C2=CC=CC=C21 BCGWQEUPMDMJNV-UHFFFAOYSA-N 0.000 claims 1
- 230000007574 infarction Effects 0.000 claims 1
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- 208000027866 inflammatory disease Diseases 0.000 claims 1
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- 229910052744 lithium Inorganic materials 0.000 claims 1
- 229960001078 lithium Drugs 0.000 claims 1
- 229960004090 maprotiline Drugs 0.000 claims 1
- QSLMDECMDJKHMQ-GSXCWMCISA-N maprotiline Chemical compound C12=CC=CC=C2[C@@]2(CCCNC)C3=CC=CC=C3[C@@H]1CC2 QSLMDECMDJKHMQ-GSXCWMCISA-N 0.000 claims 1
- NIOMSWGSBCFSGQ-UHFFFAOYSA-N methyl 2-(4-chloro-2,6-dimethylphenoxy)-6-methyl-4-(1-methylsulfanylbutan-2-ylamino)pyridine-3-carboxylate Chemical compound CSCC(CC)NC1=CC(C)=NC(OC=2C(=CC(Cl)=CC=2C)C)=C1C(=O)OC NIOMSWGSBCFSGQ-UHFFFAOYSA-N 0.000 claims 1
- XYNCUNGGOOWKHL-UHFFFAOYSA-N methyl 2-(4-chloro-2,6-dimethylphenoxy)-6-methyl-4-(oxolan-3-ylamino)pyridine-3-carboxylate Chemical compound C1=C(C)N=C(OC=2C(=CC(Cl)=CC=2C)C)C(C(=O)OC)=C1NC1CCOC1 XYNCUNGGOOWKHL-UHFFFAOYSA-N 0.000 claims 1
- UEGLRPIPCOFFEI-UHFFFAOYSA-N methyl 2-[4-chloro-2-(trifluoromethoxy)phenoxy]-6-methyl-4-(pentan-3-ylamino)pyridine-3-carboxylate Chemical compound CCC(CC)NC1=CC(C)=NC(OC=2C(=CC(Cl)=CC=2)OC(F)(F)F)=C1C(=O)OC UEGLRPIPCOFFEI-UHFFFAOYSA-N 0.000 claims 1
- 230000036651 mood Effects 0.000 claims 1
- 208000029766 myalgic encephalomeyelitis/chronic fatigue syndrome Diseases 0.000 claims 1
- 230000004693 neuron damage Effects 0.000 claims 1
- 230000003961 neuronal insult Effects 0.000 claims 1
- 239000002767 noradrenalin uptake inhibitor Substances 0.000 claims 1
- 229960001158 nortriptyline Drugs 0.000 claims 1
- 235000020824 obesity Nutrition 0.000 claims 1
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- 230000037324 pain perception Effects 0.000 claims 1
- 230000001314 paroxysmal effect Effects 0.000 claims 1
- 208000028173 post-traumatic stress disease Diseases 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 229960002601 protriptyline Drugs 0.000 claims 1
- BWPIARFWQZKAIA-UHFFFAOYSA-N protriptyline Chemical compound C1=CC2=CC=CC=C2C(CCCNC)C2=CC=CC=C21 BWPIARFWQZKAIA-UHFFFAOYSA-N 0.000 claims 1
- 229940044551 receptor antagonist Drugs 0.000 claims 1
- 239000002464 receptor antagonist Substances 0.000 claims 1
- 102000005962 receptors Human genes 0.000 claims 1
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| GB0117396D0 (en) | 2001-07-17 | 2001-09-05 | Glaxo Group Ltd | Chemical compounds |
| GB0119249D0 (en) | 2001-08-07 | 2001-10-03 | Novartis Ag | Organic compounds |
| US7323469B2 (en) | 2001-08-07 | 2008-01-29 | Novartis Ag | 7H-pyrrolo[2,3-d]pyrimidine derivatives |
| AR040456A1 (es) | 2002-06-27 | 2005-04-06 | Bristol Myers Squibb Co | Piridina n-oxidos 2,4 -disubstituidos utiles como inhibidores de transcriptasa inversa del virus de inmunodeficiencia humana |
| EP1688408A3 (en) * | 2002-08-08 | 2007-08-22 | Amgen, Inc | Vanilloid receptor ligands and their use in treatments |
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| GB0308208D0 (en) | 2003-04-09 | 2003-05-14 | Glaxo Group Ltd | Chemical compounds |
| US7112585B2 (en) | 2003-04-18 | 2006-09-26 | Bristol-Myers Squibb Company | Pyrimidine derivatives as corticotropin releasing factor inhibitors |
| US7030145B2 (en) | 2003-04-18 | 2006-04-18 | Bristol-Myers Squibb Company | Pyridinyl derivatives for the treatment of depression |
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| JP4185154B2 (ja) | 2004-04-30 | 2008-11-26 | ワーナー−ランバート カンパニー リミテッド ライアビリティー カンパニー | 中枢神経系障害治療用の置換モルホリン化合物 |
| AU2005245389A1 (en) * | 2004-05-12 | 2005-12-01 | Bristol-Myers Squibb Company | Urea antagonists of P2Y1 receptor useful in the treatment of thrombotic conditions |
| EP1827438B2 (en) | 2004-09-20 | 2014-12-10 | Xenon Pharmaceuticals Inc. | Piperazin derivatives for inhibiting human stearoyl-coa-desaturase |
| US7301022B2 (en) | 2005-02-15 | 2007-11-27 | Amgen Inc. | Vanilloid receptor ligands and their use in treatments |
| US8153791B2 (en) | 2005-12-21 | 2012-04-10 | Janssen Pharmaceutica N.V. | Substituted pyrimidinyl oxime kinase inhibitors |
| US8013153B2 (en) * | 2006-03-23 | 2011-09-06 | Janssen Pharmaceutica, N.V. | Substituted pyrimidine kinase inhibitors |
| DE602007011793D1 (de) | 2006-10-18 | 2011-02-17 | Pfizer Prod Inc | Biaryl-ether-harnstoffverbindungen |
| WO2009144632A1 (en) * | 2008-05-30 | 2009-12-03 | Pfizer Limited | Novel compounds |
| GB0913636D0 (en) * | 2009-08-05 | 2009-09-16 | Univ Leuven Kath | Novel viral replication inhibitors |
| EP3323818A1 (en) | 2010-09-22 | 2018-05-23 | Arena Pharmaceuticals, Inc. | Modulators of the gpr119 receptor and the treatment of disorders related thereto |
| DK3013813T3 (da) | 2013-06-27 | 2019-06-03 | Pfizer | Heteroaromatiske forbindelser og anvendelse deraf som dopamin-d1-ligander |
| PL3242666T3 (pl) | 2015-01-06 | 2025-02-17 | Arena Pharmaceuticals, Inc. | Związek do zastosowania w leczeniu dolegliwości związanych z receptorem s1p1 |
| AU2016229268B2 (en) | 2015-03-06 | 2020-09-10 | Pharmakea, Inc. | Fluorinated lysyl oxidase-like 2 inhibitors and uses thereof |
| EP3265445B1 (en) | 2015-03-06 | 2021-05-05 | Pharmakea, Inc. | Lysyl oxidase-like 2 inhibitors and uses thereof |
| BR112017027656B1 (pt) | 2015-06-22 | 2023-12-05 | Arena Pharmaceuticals, Inc. | Hábito cristalino de placa livre de sal de l-arginina de ácido (r)-2-(7-(4- ciclopentil-3-(trifluorometil)benzilóxi)- 1,2,3,4-tetra-hidrociclo-penta[b]indol-3- il)acético, composição farmacêutica que o compreende, seus usos e método de preparação do mesmo |
| WO2018007331A1 (en) * | 2016-07-08 | 2018-01-11 | F. Hoffmann-La Roche Ag | Fused pyrimidine derivatives |
| CA3036064A1 (en) | 2016-09-07 | 2018-03-15 | Pharmakea, Inc. | Crystalline forms of a lysyl oxidase-like 2 inhibitor and methods of making |
| WO2018048942A1 (en) | 2016-09-07 | 2018-03-15 | Pharmakea, Inc. | Uses of a lysyl oxidase-like 2 inhibitor |
| JP7187037B2 (ja) * | 2016-09-07 | 2022-12-12 | ザ リージェンツ オブ ザ ユニバーシティ オブ カリフォルニア | ｐ－タウを減少させ、認知機能を改善させるアロステリック副腎皮質刺激ホルモン放出因子受容体１（ＣＲＦＲ１）アンタゴニスト |
| MX2019009841A (es) | 2017-02-16 | 2020-01-30 | Arena Pharm Inc | Compuestos y metodos para el tratamiento de la colangitis biliar primaria. |
| ES2963044T3 (es) | 2017-03-13 | 2024-03-25 | Raqualia Pharma Inc | Derivados de tetrahidroquinolina como antagonistas del receptor P2X7 |
| CA3102136A1 (en) | 2018-06-06 | 2019-12-12 | Arena Pharmaceuticals, Inc. | Methods of treating conditions related to the s1p1 receptor |
| WO2020168068A1 (en) * | 2019-02-13 | 2020-08-20 | The University Of Vermont And State Agricultural College | Small molecule antagonist to pacap receptor and uses thereof |
| CA3160447A1 (en) * | 2019-11-06 | 2021-05-14 | Albert Einstein College Of Medicine | Small molecule prostagladin transport inhibitors |
| WO2024086061A2 (en) * | 2022-10-18 | 2024-04-25 | Merck Sharp & Dohme Llc | Novel kv3 channel modulators |
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| DE3145287A1 (de) | 1981-11-14 | 1983-05-19 | Troponwerke GmbH & Co KG, 5000 Köln | Pyrrolo (2.3-d)pyrimidine, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel |
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| WO1995010506A1 (en) * | 1993-10-12 | 1995-04-20 | The Du Pont Merck Pharmaceutical Company | 1n-alkyl-n-arylpyrimidinamines and derivatives thereof |
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| US6403599B1 (en) * | 1995-11-08 | 2002-06-11 | Pfizer Inc | Corticotropin releasing factor antagonists |
| PA8467401A1 (es) * | 1998-02-17 | 2000-09-29 | Pfizer Prod Inc | Procedimiento para tratar la insuficiencia cardiaca |
| US6130188A (en) * | 1998-05-05 | 2000-10-10 | American Cyanamid Company | Herbicidal pyridine compounds |
| EP1040831A3 (en) * | 1999-04-02 | 2003-05-02 | Pfizer Products Inc. | Use of corticotropin releasing factor (CRF) antagonists to prevent sudden death |
| US6387894B1 (en) * | 1999-06-11 | 2002-05-14 | Pfizer Inc. | Use of CRF antagonists and renin-angiotensin system inhibitors |
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- 2001-01-05 CN CN01803846A patent/CN1395566A/zh active Pending
- 2001-01-05 YU YU54402A patent/YU54402A/sh unknown
- 2001-01-05 CA CA002397633A patent/CA2397633A1/en not_active Abandoned
- 2001-01-05 AU AU23905/01A patent/AU779995B2/en not_active Ceased
- 2001-01-05 JP JP2001553267A patent/JP2003520272A/ja active Pending
- 2001-01-05 AP APAP/P/2002/002583A patent/AP2002002583A0/en unknown
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- 2001-01-05 BR BR0107662-0A patent/BR0107662A/pt not_active IP Right Cessation
- 2001-01-05 WO PCT/IB2001/000004 patent/WO2001053263A1/en not_active Ceased
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