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 |
| US7323469B2 (en) | 2001-08-07 | 2008-01-29 | Novartis Ag | 7H-pyrrolo[2,3-d]pyrimidine derivatives |
| GB0119249D0 (en) | 2001-08-07 | 2001-10-03 | Novartis Ag | Organic compounds |
| TW200409629A (en) | 2002-06-27 | 2004-06-16 | Bristol Myers Squibb Co | 2,4-disubstituted-pyridine N-oxides useful as HIV reverse transcriptase inhibitors |
| AR041191A1 (es) | 2002-08-08 | 2005-05-04 | Amgen Inc | Ligandos del receptor vanilloide y su uso en tratamientos |
| EP1688408A3 (en) * | 2002-08-08 | 2007-08-22 | Amgen, Inc | Vanilloid receptor ligands and their use in treatments |
| DE602004009295T2 (de) | 2003-01-14 | 2008-07-03 | Arena Pharmaceuticals, Inc., San Diego | 1,2,3-trisubstituierte aryl- und heteroarylderivate als modulatoren des metabolismus zur vorbeugung und behandlung von metabolismus-bedingten krankheiten wie diabetes oder hyperglykämie |
| ATE359782T1 (de) * | 2003-01-16 | 2007-05-15 | Sb Pharmco Inc | Heteroaryl-substituierte pyrrol(2, 3- b)pyridin- derivate als crf-rezeptor-antagonisten |
| GB0308208D0 (en) | 2003-04-09 | 2003-05-14 | Glaxo Group Ltd | Chemical compounds |
| US7030145B2 (en) | 2003-04-18 | 2006-04-18 | Bristol-Myers Squibb Company | Pyridinyl derivatives for the treatment of depression |
| US7112585B2 (en) | 2003-04-18 | 2006-09-26 | Bristol-Myers Squibb Company | Pyrimidine derivatives as corticotropin releasing factor inhibitors |
| AR045047A1 (es) | 2003-07-11 | 2005-10-12 | Arena Pharm Inc | Derivados arilo y heteroarilo trisustituidos como moduladores del metabolismo y de la profilaxis y tratamiento de desordenes relacionados con los mismos |
| EP2292620A3 (en) | 2003-07-14 | 2011-06-22 | Arena Pharmaceuticals, Inc. | Fused-aryl and heteroaryl derivatives as modulators of metabolism and the prohylaxis and treatment of disorders related thereto |
| US20050171095A1 (en) * | 2004-01-06 | 2005-08-04 | Pfizer Inc | Combination of CRF antagonists and 5-HT1B receptor antagonists |
| CN1910190A (zh) * | 2004-01-06 | 2007-02-07 | 大正制药株式会社 | 环氨基取代的噻吩并嘧啶和噻吩并吡啶衍生物 |
| MY139645A (en) | 2004-02-11 | 2009-10-30 | Amgen Inc | Vanilloid receptor ligands and their use in treatments |
| US7534798B2 (en) | 2004-02-11 | 2009-05-19 | Amgen Inc. | Vanilloid receptor ligands and their use in treatments |
| CA2564994A1 (en) | 2004-04-30 | 2005-11-10 | Warner-Lambert Company Llc | Substituted morpholine compounds for the treatment of central nervous system disorders |
| JP2008500284A (ja) * | 2004-05-12 | 2008-01-10 | ブリストル−マイヤーズ スクイブ カンパニー | 血栓症の治療に有用なｐ２ｙ１レセプターのウレアアンタゴニスト |
| CN101090724A (zh) | 2004-09-20 | 2007-12-19 | 泽农医药公司 | 用于抑制人硬脂酰CoA去饱和酶的吡啶衍生物 |
| WO2006089311A1 (en) | 2005-02-15 | 2006-08-24 | 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 |
| WO2007109783A2 (en) * | 2006-03-23 | 2007-09-27 | Janssen Pharmaceutica, N.V. | Substituted pyrimidine kinase inhibitors |
| GEP20125425B (en) | 2006-10-18 | 2012-03-26 | Pfizer Prod Inc | Biaryl ether urea compounds |
| 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 |
| PH12013500547A1 (en) | 2010-09-22 | 2013-06-10 | Arena Pharm Inc | Modulators of the gpr119 receptor and the treatment of disorders related thereto |
| FI3421462T3 (fi) | 2013-06-27 | 2023-06-26 | Pfizer | Heteroaromaattisia yhdisteitä ja niiden käyttö dopamiini-d1-ligandeina |
| ES2995737T3 (en) | 2015-01-06 | 2025-02-11 | Arena Pharm Inc | Compound for use in treating conditions related to the s1p1 receptor |
| KR102594441B1 (ko) | 2015-03-06 | 2023-10-25 | 파마케아, 인크. | 플루오르화된 리실 옥시다아제-유사 2 억제제 및 이의 용도 |
| US10766860B2 (en) | 2015-03-06 | 2020-09-08 | Pharmakea, Inc. | Lysyl oxidase-like 2 inhibitors and uses thereof |
| MA42807A (fr) | 2015-06-22 | 2018-07-25 | Arena Pharm Inc | Sel l-arginine cristallin d'acide (r)-2-(7-(4-cyclopentyl-3-(trifluorométhyl)benzyloxy)-1,2,3,4-tétrahydrocyclo-penta[b]indol-3-yl)acétique (composé 1) pour une utilisation dans des troubles associés au récepteur de s1p1 |
| EP3481829B1 (en) * | 2016-07-08 | 2021-04-07 | H. Hoffnabb-La Roche Ag | Fused pyrimidine derivatives |
| AU2017324445A1 (en) | 2016-09-07 | 2019-04-11 | Pharmakea, Inc. | Crystalline forms of a lysyl oxidase-like 2 inhibitor and methods of making |
| BR112019004513A2 (pt) | 2016-09-07 | 2019-06-18 | Pharmakea Inc | usos de um inibidor de lisil oxidase-like 2 |
| KR102571296B1 (ko) * | 2016-09-07 | 2023-08-28 | 더 리전트 오브 더 유니버시티 오브 캘리포니아 | P-tau를 감소시키고 인지를 개선하는 알로스테릭 코르티코트로핀-방출 인자 수용체 1 (crfr1) 길항제 |
| WO2018151873A1 (en) | 2017-02-16 | 2018-08-23 | Arena Pharmaceuticals, Inc. | Compounds and methods for treatment of primary biliary cholangitis |
| RU2724350C1 (ru) | 2017-03-13 | 2020-06-23 | Раквалиа Фарма Инк. | Производные тетрагидрохинолина в качестве антагонистов рецептора р2х7 |
| EP3801459B1 (en) | 2018-06-06 | 2024-08-07 | 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 |
| WO2021091823A1 (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 |
| US4605642A (en) | 1984-02-23 | 1986-08-12 | The Salk Institute For Biological Studies | CRF antagonists |
| EP0264883A3 (en) | 1986-10-21 | 1990-04-04 | Banyu Pharmaceutical Co., Ltd. | Substituted pyridine derivatives |
| US5063245A (en) | 1990-03-28 | 1991-11-05 | Nova Pharmaceutical Corporation | Corticotropin-releasing factor antagonism compounds |
| AU647822B2 (en) | 1990-09-14 | 1994-03-31 | Marion Merrell Dow Inc. | Novel carbocyclic adenosine analogs useful as immunosuppressants |
| EP0582804B1 (de) | 1992-08-10 | 1996-09-25 | Volkswagen Aktiengesellschaft | Schalteinrichtung für ein Getriebe |
| CZ286892B6 (en) * | 1992-12-17 | 2000-07-12 | Pfizer | Pyrrolopyrimidine compounds, intermediates for their preparation and pharmaceutical preparations based thereon |
| RU2153494C2 (ru) * | 1993-10-12 | 2000-07-27 | Дзе Дюпон Мерк Фармасьютикал Компани | 1-n-алкил-n-арилпиримидинамины, способ лечения заболеваний, фармацевтическая композиция |
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| US5691364A (en) | 1995-03-10 | 1997-11-25 | Berlex Laboratories, Inc. | Benzamidine derivatives and their use as anti-coagulants |
| 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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