MX2008015489A - Compuestos organicos. - Google Patents
Compuestos organicos.Info
- Publication number
- MX2008015489A MX2008015489A MX2008015489A MX2008015489A MX2008015489A MX 2008015489 A MX2008015489 A MX 2008015489A MX 2008015489 A MX2008015489 A MX 2008015489A MX 2008015489 A MX2008015489 A MX 2008015489A MX 2008015489 A MX2008015489 A MX 2008015489A
- Authority
- MX
- Mexico
- Prior art keywords
- methyl
- pyrimidine
- pyrazolo
- dione
- benzyl
- Prior art date
Links
- 150000002894 organic compounds Chemical class 0.000 title description 2
- 150000003839 salts Chemical group 0.000 claims abstract description 19
- 239000000651 prodrug Chemical group 0.000 claims abstract description 12
- 229940002612 prodrug Drugs 0.000 claims abstract description 12
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 11
- 239000003814 drug Substances 0.000 claims abstract description 10
- 150000001875 compounds Chemical class 0.000 claims description 109
- -1 4- (trifluoromethyl) benzyl Chemical group 0.000 claims description 60
- 238000000034 method Methods 0.000 claims description 52
- RJKFOVLPORLFTN-LEKSSAKUSA-N Progesterone Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 RJKFOVLPORLFTN-LEKSSAKUSA-N 0.000 claims description 38
- 125000000217 alkyl group Chemical group 0.000 claims description 27
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 26
- 230000000694 effects Effects 0.000 claims description 21
- 239000000186 progesterone Substances 0.000 claims description 19
- 201000010099 disease Diseases 0.000 claims description 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 17
- 229960003387 progesterone Drugs 0.000 claims description 17
- 238000011282 treatment Methods 0.000 claims description 17
- 125000003118 aryl group Chemical group 0.000 claims description 15
- 230000001965 increasing effect Effects 0.000 claims description 15
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 14
- 125000001188 haloalkyl group Chemical group 0.000 claims description 13
- 229910052736 halogen Inorganic materials 0.000 claims description 13
- 150000002367 halogens Chemical class 0.000 claims description 13
- 125000001072 heteroaryl group Chemical group 0.000 claims description 13
- 125000004076 pyridyl group Chemical group 0.000 claims description 12
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 11
- 230000002829 reductive effect Effects 0.000 claims description 11
- 229940011871 estrogen Drugs 0.000 claims description 10
- 239000000262 estrogen Substances 0.000 claims description 10
- 230000011664 signaling Effects 0.000 claims description 10
- 208000018737 Parkinson disease Diseases 0.000 claims description 9
- 201000003631 narcolepsy Diseases 0.000 claims description 8
- HXNFUBHNUDHIGC-UHFFFAOYSA-N oxypurinol Chemical compound O=C1NC(=O)N=C2NNC=C21 HXNFUBHNUDHIGC-UHFFFAOYSA-N 0.000 claims description 8
- 230000005764 inhibitory process Effects 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 claims description 6
- 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 claims description 6
- 102000004076 Dopamine D1 Receptors Human genes 0.000 claims description 6
- 108090000511 Dopamine D1 Receptors Proteins 0.000 claims description 6
- 206010057671 Female sexual dysfunction Diseases 0.000 claims description 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 6
- 239000008194 pharmaceutical composition Substances 0.000 claims description 6
- 230000019491 signal transduction Effects 0.000 claims description 6
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims description 5
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims description 5
- 125000000278 alkyl amino alkyl group Chemical group 0.000 claims description 5
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 5
- 239000003085 diluting agent Substances 0.000 claims description 5
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 5
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 5
- VOXZDWNPVJITMN-ZBRFXRBCSA-N 17β-estradiol Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 VOXZDWNPVJITMN-ZBRFXRBCSA-N 0.000 claims description 4
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 4
- 241001435619 Lile Species 0.000 claims description 4
- 208000005793 Restless legs syndrome Diseases 0.000 claims description 4
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims description 4
- 230000006378 damage Effects 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- 229960005309 estradiol Drugs 0.000 claims description 4
- 229930182833 estradiol Natural products 0.000 claims description 4
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 4
- 208000003532 hypothyroidism Diseases 0.000 claims description 4
- 230000002989 hypothyroidism Effects 0.000 claims description 4
- 239000000583 progesterone congener Substances 0.000 claims description 4
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 3
- AYFWOHAHSGBBKN-UHFFFAOYSA-N 3-anilino-7-[(4-methoxyphenyl)methyl]-5-methyl-2-[(4-pyridin-2-ylphenyl)methyl]pyrazolo[3,4-d]pyrimidine-4,6-dione Chemical compound C1=CC(OC)=CC=C1CN1C(=O)N(C)C(=O)C2=C(NC=3C=CC=CC=3)N(CC=3C=CC(=CC=3)C=3N=CC=CC=3)N=C21 AYFWOHAHSGBBKN-UHFFFAOYSA-N 0.000 claims description 3
- 208000024827 Alzheimer disease Diseases 0.000 claims description 3
- 201000000736 Amenorrhea Diseases 0.000 claims description 3
- 206010001928 Amenorrhoea Diseases 0.000 claims description 3
- 206010003805 Autism Diseases 0.000 claims description 3
- 208000020706 Autistic disease Diseases 0.000 claims description 3
- 208000023275 Autoimmune disease Diseases 0.000 claims description 3
- 208000028698 Cognitive impairment Diseases 0.000 claims description 3
- 206010014733 Endometrial cancer Diseases 0.000 claims description 3
- 206010014759 Endometrial neoplasm Diseases 0.000 claims description 3
- 208000023105 Huntington disease Diseases 0.000 claims description 3
- 208000000323 Tourette Syndrome Diseases 0.000 claims description 3
- 208000016620 Tourette disease Diseases 0.000 claims description 3
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 3
- 231100000540 amenorrhea Toxicity 0.000 claims description 3
- 208000010877 cognitive disease Diseases 0.000 claims description 3
- 229940079593 drug Drugs 0.000 claims description 3
- 201000003914 endometrial carcinoma Diseases 0.000 claims description 3
- 206010020718 hyperplasia Diseases 0.000 claims description 3
- 208000000509 infertility Diseases 0.000 claims description 3
- 230000036512 infertility Effects 0.000 claims description 3
- 231100000535 infertility Toxicity 0.000 claims description 3
- 208000027866 inflammatory disease Diseases 0.000 claims description 3
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 3
- 125000001425 triazolyl group Chemical group 0.000 claims description 3
- PROQIPRRNZUXQM-UHFFFAOYSA-N (16alpha,17betaOH)-Estra-1,3,5(10)-triene-3,16,17-triol Natural products OC1=CC=C2C3CCC(C)(C(C(O)C4)O)C4C3CCC2=C1 PROQIPRRNZUXQM-UHFFFAOYSA-N 0.000 claims description 2
- YFGHCGITMMYXAQ-UHFFFAOYSA-N 2-[(diphenylmethyl)sulfinyl]acetamide Chemical compound C=1C=CC=CC=1C(S(=O)CC(=O)N)C1=CC=CC=C1 YFGHCGITMMYXAQ-UHFFFAOYSA-N 0.000 claims description 2
- YYUFAGPHSNHYSJ-UHFFFAOYSA-N 3-[(4-fluorophenyl)methylamino]-5-methyl-7-(2-methylpropyl)-2-[[4-(trifluoromethyl)phenyl]methyl]pyrazolo[3,4-d]pyrimidine-4,6-dione Chemical compound C=1C=C(F)C=CC=1CNC1=C2C(=O)N(C)C(=O)N(CC(C)C)C2=NN1CC1=CC=C(C(F)(F)F)C=C1 YYUFAGPHSNHYSJ-UHFFFAOYSA-N 0.000 claims description 2
- YQDNWIPJGMMJDQ-UHFFFAOYSA-N 3-anilino-5-methyl-2-[(4-pyridin-2-ylphenyl)methyl]-7-(2,2,2-trifluoroethyl)pyrazolo[3,4-d]pyrimidine-4,6-dione Chemical compound C=1C=CC=CC=1NC1=C2C(=O)N(C)C(=O)N(CC(F)(F)F)C2=NN1CC(C=C1)=CC=C1C1=CC=CC=N1 YQDNWIPJGMMJDQ-UHFFFAOYSA-N 0.000 claims description 2
- PKNOJFZRKNTJGM-UHFFFAOYSA-N 3-anilino-5-methyl-7-(2-methylpropyl)-2-[(4-phenylphenyl)methyl]pyrazolo[3,4-d]pyrimidine-4,6-dione Chemical compound C=1C=CC=CC=1NC1=C2C(=O)N(C)C(=O)N(CC(C)C)C2=NN1CC(C=C1)=CC=C1C1=CC=CC=C1 PKNOJFZRKNTJGM-UHFFFAOYSA-N 0.000 claims description 2
- BHSMCJPUJATFHJ-UHFFFAOYSA-N 3-anilino-5-methyl-7-(oxolan-2-ylmethyl)-2-[(4-pyridin-2-ylphenyl)methyl]pyrazolo[3,4-d]pyrimidine-4,6-dione Chemical compound C12=NN(CC=3C=CC(=CC=3)C=3N=CC=CC=3)C(NC=3C=CC=CC=3)=C2C(=O)N(C)C(=O)N1CC1CCCO1 BHSMCJPUJATFHJ-UHFFFAOYSA-N 0.000 claims description 2
- GYXHFBYLBQNPMJ-UHFFFAOYSA-N 3-anilino-7-cyclohexyl-5-methyl-2-[(4-pyridin-2-ylphenyl)methyl]pyrazolo[3,4-d]pyrimidine-4,6-dione Chemical compound C12=NN(CC=3C=CC(=CC=3)C=3N=CC=CC=3)C(NC=3C=CC=CC=3)=C2C(=O)N(C)C(=O)N1C1CCCCC1 GYXHFBYLBQNPMJ-UHFFFAOYSA-N 0.000 claims description 2
- XRZNMYDPYYRTHA-UHFFFAOYSA-N 7-[(4-methoxyphenyl)methyl]-5-methyl-2-[(4-phenylphenyl)methyl]-3-[n-[(4-phenylphenyl)methyl]anilino]pyrazolo[3,4-d]pyrimidine-4,6-dione Chemical compound C1=CC(OC)=CC=C1CN1C(=O)N(C)C(=O)C2=C(N(CC=3C=CC(=CC=3)C=3C=CC=CC=3)C=3C=CC=CC=3)N(CC=3C=CC(=CC=3)C=3C=CC=CC=3)N=C21 XRZNMYDPYYRTHA-UHFFFAOYSA-N 0.000 claims description 2
- 208000037853 Abnormal uterine bleeding Diseases 0.000 claims description 2
- 208000019901 Anxiety disease Diseases 0.000 claims description 2
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 2
- 206010012289 Dementia Diseases 0.000 claims description 2
- 208000012661 Dyskinesia Diseases 0.000 claims description 2
- 208000001914 Fragile X syndrome Diseases 0.000 claims description 2
- 201000004311 Gilles de la Tourette syndrome Diseases 0.000 claims description 2
- 206010020772 Hypertension Diseases 0.000 claims description 2
- 206010027304 Menopausal symptoms Diseases 0.000 claims description 2
- 206010027339 Menstruation irregular Diseases 0.000 claims description 2
- 208000016285 Movement disease Diseases 0.000 claims description 2
- 208000001132 Osteoporosis Diseases 0.000 claims description 2
- 208000006399 Premature Obstetric Labor Diseases 0.000 claims description 2
- 206010060862 Prostate cancer Diseases 0.000 claims description 2
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 2
- 206010051482 Prostatomegaly Diseases 0.000 claims description 2
- 206010039085 Rhinitis allergic Diseases 0.000 claims description 2
- 201000001880 Sexual dysfunction Diseases 0.000 claims description 2
- 206010044565 Tremor Diseases 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 201000010105 allergic rhinitis Diseases 0.000 claims description 2
- 239000000935 antidepressant agent Substances 0.000 claims description 2
- 229940005513 antidepressants Drugs 0.000 claims description 2
- 230000036506 anxiety Effects 0.000 claims description 2
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 2
- 208000006673 asthma Diseases 0.000 claims description 2
- 230000001363 autoimmune Effects 0.000 claims description 2
- 210000003169 central nervous system Anatomy 0.000 claims description 2
- 208000026106 cerebrovascular disease Diseases 0.000 claims description 2
- 230000001149 cognitive effect Effects 0.000 claims description 2
- 230000003292 diminished effect Effects 0.000 claims description 2
- 206010013663 drug dependence Diseases 0.000 claims description 2
- PROQIPRRNZUXQM-ZXXIGWHRSA-N estriol Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@H]([C@H](O)C4)O)[C@@H]4[C@@H]3CCC2=C1 PROQIPRRNZUXQM-ZXXIGWHRSA-N 0.000 claims description 2
- 229960001348 estriol Drugs 0.000 claims description 2
- 125000005223 heteroarylcarbonyl group Chemical group 0.000 claims description 2
- 208000035231 inattentive type attention deficit hyperactivity disease Diseases 0.000 claims description 2
- 230000009245 menopause Effects 0.000 claims description 2
- 229960001165 modafinil Drugs 0.000 claims description 2
- 201000006417 multiple sclerosis Diseases 0.000 claims description 2
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 2
- 239000003368 psychostimulant agent Substances 0.000 claims description 2
- 208000002815 pulmonary hypertension Diseases 0.000 claims description 2
- 231100000872 sexual dysfunction Toxicity 0.000 claims description 2
- 208000019116 sleep disease Diseases 0.000 claims description 2
- 208000011117 substance-related disease Diseases 0.000 claims description 2
- ZOOGRGPOEVQQDX-UUOKFMHZSA-N 3',5'-cyclic GMP Chemical compound C([C@H]1O2)OP(O)(=O)O[C@H]1[C@@H](O)[C@@H]2N1C(N=C(NC2=O)N)=C2N=C1 ZOOGRGPOEVQQDX-UUOKFMHZSA-N 0.000 claims 2
- LKFJFBMOTUNCQS-UHFFFAOYSA-N 3-anilino-7-[(4-methoxyphenyl)methyl]-5-methyl-2-[(4-phenylphenyl)methyl]pyrazolo[3,4-d]pyrimidine-4,6-dione Chemical compound C1=CC(OC)=CC=C1CN1C(=O)N(C)C(=O)C2=C(NC=3C=CC=CC=3)N(CC=3C=CC(=CC=3)C=3C=CC=CC=3)N=C21 LKFJFBMOTUNCQS-UHFFFAOYSA-N 0.000 claims 1
- SJZRECIVHVDYJC-UHFFFAOYSA-M 4-hydroxybutyrate Chemical compound OCCCC([O-])=O SJZRECIVHVDYJC-UHFFFAOYSA-M 0.000 claims 1
- 201000005670 Anovulation Diseases 0.000 claims 1
- 206010002659 Anovulatory cycle Diseases 0.000 claims 1
- 206010007559 Cardiac failure congestive Diseases 0.000 claims 1
- 206010010904 Convulsion Diseases 0.000 claims 1
- 101001117089 Drosophila melanogaster Calcium/calmodulin-dependent 3',5'-cyclic nucleotide phosphodiesterase 1 Proteins 0.000 claims 1
- 206010036618 Premenstrual syndrome Diseases 0.000 claims 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 1
- 231100000552 anovulation Toxicity 0.000 claims 1
- 201000001514 prostate carcinoma Diseases 0.000 claims 1
- 208000020685 sleep-wake disease Diseases 0.000 claims 1
- 239000000021 stimulant Substances 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical group C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
- 101001117086 Dictyostelium discoideum cAMP/cGMP-dependent 3',5'-cAMP/cGMP phosphodiesterase A Proteins 0.000 abstract description 16
- 239000003112 inhibitor Substances 0.000 abstract description 6
- 238000001819 mass spectrum Methods 0.000 description 23
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
- 102100024318 Calcium/calmodulin-dependent 3',5'-cyclic nucleotide phosphodiesterase 1B Human genes 0.000 description 16
- 101001117099 Homo sapiens Calcium/calmodulin-dependent 3',5'-cyclic nucleotide phosphodiesterase 1B Proteins 0.000 description 16
- ZOOGRGPOEVQQDX-KHLHZJAASA-N cyclic guanosine monophosphate Chemical compound C([C@H]1O2)O[P@](O)(=O)O[C@@H]1[C@H](O)[C@H]2N1C(N=C(NC2=O)N)=C2N=C1 ZOOGRGPOEVQQDX-KHLHZJAASA-N 0.000 description 16
- 238000001308 synthesis method Methods 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- 229940121836 Phosphodiesterase 1 inhibitor Drugs 0.000 description 11
- 108090001050 Phosphoric Diester Hydrolases Proteins 0.000 description 11
- 102000004861 Phosphoric Diester Hydrolases Human genes 0.000 description 11
- 230000015572 biosynthetic process Effects 0.000 description 11
- 238000003786 synthesis reaction Methods 0.000 description 11
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 10
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 10
- 229910000027 potassium carbonate Inorganic materials 0.000 description 10
- BTUGGGLMQBJCBN-UHFFFAOYSA-N 1-iodo-2-methylpropane Chemical compound CC(C)CI BTUGGGLMQBJCBN-UHFFFAOYSA-N 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- 241000700159 Rattus Species 0.000 description 8
- 208000035475 disorder Diseases 0.000 description 8
- 239000000543 intermediate Substances 0.000 description 8
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 102000004190 Enzymes Human genes 0.000 description 6
- 108090000790 Enzymes Proteins 0.000 description 6
- 208000007623 Lordosis Diseases 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 230000004913 activation Effects 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 125000004122 cyclic group Chemical group 0.000 description 6
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 239000000741 silica gel Substances 0.000 description 6
- 229910002027 silica gel Inorganic materials 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 238000004809 thin layer chromatography Methods 0.000 description 6
- 102000012749 Dopamine and cAMP-Regulated Phosphoprotein 32 Human genes 0.000 description 5
- 108010090047 Dopamine and cAMP-Regulated Phosphoprotein 32 Proteins 0.000 description 5
- 241001465754 Metazoa Species 0.000 description 5
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 5
- 210000004027 cell Anatomy 0.000 description 5
- 239000003153 chemical reaction reagent Substances 0.000 description 5
- 229960003638 dopamine Drugs 0.000 description 5
- 238000004992 fast atom bombardment mass spectroscopy Methods 0.000 description 5
- 238000003818 flash chromatography Methods 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- 230000003834 intracellular effect Effects 0.000 description 5
- 230000031146 intracellular signal transduction Effects 0.000 description 5
- 230000007781 signaling event Effects 0.000 description 5
- 210000001519 tissue Anatomy 0.000 description 5
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 5
- MOHYOXXOKFQHDC-UHFFFAOYSA-N 1-(chloromethyl)-4-methoxybenzene Chemical compound COC1=CC=C(CCl)C=C1 MOHYOXXOKFQHDC-UHFFFAOYSA-N 0.000 description 4
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 4
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 4
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 4
- 102100024316 Calcium/calmodulin-dependent 3',5'-cyclic nucleotide phosphodiesterase 1A Human genes 0.000 description 4
- 102100024317 Calcium/calmodulin-dependent 3',5'-cyclic nucleotide phosphodiesterase 1C Human genes 0.000 description 4
- 101001117044 Homo sapiens Calcium/calmodulin-dependent 3',5'-cyclic nucleotide phosphodiesterase 1A Proteins 0.000 description 4
- 101001117094 Homo sapiens Calcium/calmodulin-dependent 3',5'-cyclic nucleotide phosphodiesterase 1C Proteins 0.000 description 4
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- OIRDTQYFTABQOQ-KQYNXXCUSA-N adenosine Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O OIRDTQYFTABQOQ-KQYNXXCUSA-N 0.000 description 4
- 210000004556 brain Anatomy 0.000 description 4
- 239000011575 calcium Substances 0.000 description 4
- 229910052791 calcium Inorganic materials 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- 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 4
- 230000003247 decreasing effect Effects 0.000 description 4
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 4
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 238000011321 prophylaxis Methods 0.000 description 4
- 230000004044 response Effects 0.000 description 4
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 4
- RQFCJASXJCIDSX-UHFFFAOYSA-N 14C-Guanosin-5'-monophosphat Natural products C1=2NC(N)=NC(=O)C=2N=CN1C1OC(COP(O)(O)=O)C(O)C1O RQFCJASXJCIDSX-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 102000003678 AMPA Receptors Human genes 0.000 description 3
- 108090000078 AMPA Receptors Proteins 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 102000008130 Cyclic AMP-Dependent Protein Kinases Human genes 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 102000004980 Dopamine D2 Receptors Human genes 0.000 description 3
- 108090001111 Dopamine D2 Receptors Proteins 0.000 description 3
- 108050004812 Dopamine receptor Proteins 0.000 description 3
- 102000015554 Dopamine receptor Human genes 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 3
- 238000003556 assay Methods 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 238000011260 co-administration Methods 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 125000001153 fluoro group Chemical group F* 0.000 description 3
- RQFCJASXJCIDSX-UUOKFMHZSA-N guanosine 5'-monophosphate Chemical compound C1=2NC(N)=NC(=O)C=2N=CN1[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O RQFCJASXJCIDSX-UUOKFMHZSA-N 0.000 description 3
- 238000002657 hormone replacement therapy Methods 0.000 description 3
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 108090000623 proteins and genes Proteins 0.000 description 3
- 230000001105 regulatory effect Effects 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 229940124597 therapeutic agent Drugs 0.000 description 3
- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 2
- YUSCRGFYKCAQHE-HQFNMCNFSA-N (8r,9s,13s,14s,17s)-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-3,17-diol;(8r,9s,13s,14s,16r,17r)-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-3,16,17-triol Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1.OC1=CC=C2[C@H]3CC[C@](C)([C@H]([C@H](O)C4)O)[C@@H]4[C@@H]3CCC2=C1 YUSCRGFYKCAQHE-HQFNMCNFSA-N 0.000 description 2
- GZYKBCXBOOXTTM-UHFFFAOYSA-N 3-anilino-5-methyl-2-[(4-pyridin-2-ylphenyl)methyl]-1h-pyrazolo[3,4-d]pyrimidine-4,6-dione Chemical compound C=1C=CC=CC=1NC1=C2C(=O)N(C)C(=O)NC2=NN1CC(C=C1)=CC=C1C1=CC=CC=N1 GZYKBCXBOOXTTM-UHFFFAOYSA-N 0.000 description 2
- NSZSICWLXFCCRN-UHFFFAOYSA-N 6-chloro-3-methyl-1-(2-methylpropyl)pyrimidine-2,4-dione Chemical compound CC(C)CN1C(Cl)=CC(=O)N(C)C1=O NSZSICWLXFCCRN-UHFFFAOYSA-N 0.000 description 2
- PTXRYWYSWRFJJO-UHFFFAOYSA-N 6-hydrazinyl-3-methyl-1-(2-methylpropyl)pyrimidine-2,4-dione Chemical compound CC(C)CN1C(NN)=CC(=O)N(C)C1=O PTXRYWYSWRFJJO-UHFFFAOYSA-N 0.000 description 2
- 101150051188 Adora2a gene Proteins 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- 239000002126 C01EB10 - Adenosine Substances 0.000 description 2
- 102000000584 Calmodulin Human genes 0.000 description 2
- 108010041952 Calmodulin Proteins 0.000 description 2
- 102000018208 Cannabinoid Receptor Human genes 0.000 description 2
- 108050007331 Cannabinoid receptor Proteins 0.000 description 2
- 108010049894 Cyclic AMP-Dependent Protein Kinases Proteins 0.000 description 2
- 102000004654 Cyclic GMP-Dependent Protein Kinases Human genes 0.000 description 2
- 108010003591 Cyclic GMP-Dependent Protein Kinases Proteins 0.000 description 2
- 102000009025 Endorphins Human genes 0.000 description 2
- 108010049140 Endorphins Proteins 0.000 description 2
- WTDRDQBEARUVNC-LURJTMIESA-N L-DOPA Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-LURJTMIESA-N 0.000 description 2
- WTDRDQBEARUVNC-UHFFFAOYSA-N L-Dopa Natural products OC(=O)C(N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-UHFFFAOYSA-N 0.000 description 2
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 2
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
- 241000124008 Mammalia Species 0.000 description 2
- 102100026933 Myelin-associated neurite-outgrowth inhibitor Human genes 0.000 description 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
- 102000004868 N-Methyl-D-Aspartate Receptors Human genes 0.000 description 2
- 108090001041 N-Methyl-D-Aspartate Receptors Proteins 0.000 description 2
- 108020001621 Natriuretic Peptide Proteins 0.000 description 2
- 102000004571 Natriuretic peptide Human genes 0.000 description 2
- 101800001814 Neurotensin Proteins 0.000 description 2
- 102000050267 Neurotensin Human genes 0.000 description 2
- 241000283984 Rodentia Species 0.000 description 2
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 2
- 229960004373 acetylcholine Drugs 0.000 description 2
- 229960005305 adenosine Drugs 0.000 description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 210000004227 basal ganglia Anatomy 0.000 description 2
- 239000011324 bead Substances 0.000 description 2
- 239000000872 buffer Substances 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 210000001638 cerebellum Anatomy 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 230000001419 dependent effect Effects 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 239000003136 dopamine receptor stimulating agent Substances 0.000 description 2
- 230000002708 enhancing effect Effects 0.000 description 2
- 229940008359 estradiol / estriol Drugs 0.000 description 2
- 229940086018 estradiol / progesterone Drugs 0.000 description 2
- 235000019439 ethyl acetate Nutrition 0.000 description 2
- 238000002875 fluorescence polarization Methods 0.000 description 2
- 230000006870 function Effects 0.000 description 2
- 229960003692 gamma aminobutyric acid Drugs 0.000 description 2
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 description 2
- 229930195712 glutamate Natural products 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 239000000411 inducer Substances 0.000 description 2
- 230000006698 induction Effects 0.000 description 2
- VBUWHHLIZKOSMS-RIWXPGAOSA-N invicorp Chemical compound C([C@@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CO)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(N)=O)C(O)=O)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CCCCN)NC(=O)[C@@H](NC(=O)[C@H](C)NC(=O)[C@H](CCSC)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@@H](NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(O)=O)NC(=O)[C@@H](NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@@H](NC(=O)[C@H](C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](N)CC=1NC=NC=1)C(C)C)[C@@H](C)O)[C@@H](C)O)C(C)C)C1=CC=C(O)C=C1 VBUWHHLIZKOSMS-RIWXPGAOSA-N 0.000 description 2
- 239000012948 isocyanate Substances 0.000 description 2
- 150000002540 isothiocyanates Chemical class 0.000 description 2
- 229960004502 levodopa Drugs 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- 239000000692 natriuretic peptide Substances 0.000 description 2
- 210000000653 nervous system Anatomy 0.000 description 2
- PCJGZPGTCUMMOT-ISULXFBGSA-N neurotensin Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC(C)C)C(O)=O)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CCCCN)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CC(C)C)NC(=O)[C@H]1NC(=O)CC1)C1=CC=C(O)C=C1 PCJGZPGTCUMMOT-ISULXFBGSA-N 0.000 description 2
- 230000002474 noradrenergic effect Effects 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 230000026731 phosphorylation Effects 0.000 description 2
- 238000006366 phosphorylation reaction Methods 0.000 description 2
- 230000006461 physiological response Effects 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 102000003998 progesterone receptors Human genes 0.000 description 2
- 108090000468 progesterone receptors Proteins 0.000 description 2
- 125000006239 protecting group Chemical group 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- 125000004353 pyrazol-1-yl group Chemical group [H]C1=NN(*)C([H])=C1[H] 0.000 description 2
- 239000011535 reaction buffer Substances 0.000 description 2
- 201000000980 schizophrenia Diseases 0.000 description 2
- 229940076279 serotonin Drugs 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 208000011580 syndromic disease Diseases 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- 230000026683 transduction Effects 0.000 description 2
- 238000010361 transduction Methods 0.000 description 2
- 239000003981 vehicle Substances 0.000 description 2
- IRICHAOGAOFEQI-UHFFFAOYSA-N (1-bromo-2,2,2-trifluoroethyl)benzene Chemical compound FC(F)(F)C(Br)C1=CC=CC=C1 IRICHAOGAOFEQI-UHFFFAOYSA-N 0.000 description 1
- RHBHXHXNWHTGSO-YFKPBYRVSA-N (2s)-1-iodo-2-methylbutane Chemical compound CC[C@H](C)CI RHBHXHXNWHTGSO-YFKPBYRVSA-N 0.000 description 1
- KIBOHRIGZMLNNS-SCSAIBSYSA-N (2s)-3-bromo-2-methylpropan-1-ol Chemical compound OC[C@H](C)CBr KIBOHRIGZMLNNS-SCSAIBSYSA-N 0.000 description 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 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 description 1
- KWTSXDURSIMDCE-QMMMGPOBSA-N (S)-amphetamine Chemical compound C[C@H](N)CC1=CC=CC=C1 KWTSXDURSIMDCE-QMMMGPOBSA-N 0.000 description 1
- 125000004512 1,2,3-thiadiazol-4-yl group Chemical group S1N=NC(=C1)* 0.000 description 1
- 125000003626 1,2,4-triazol-1-yl group Chemical group [*]N1N=C([H])N=C1[H] 0.000 description 1
- HGKPAXHJTMHWAH-UHFFFAOYSA-N 1-(bromomethyl)-4-methylsulfonylbenzene Chemical compound CS(=O)(=O)C1=CC=C(CBr)C=C1 HGKPAXHJTMHWAH-UHFFFAOYSA-N 0.000 description 1
- PHNRBSHOFSWNII-UHFFFAOYSA-N 1-[4-(bromomethyl)phenyl]pyrazole Chemical compound C1=CC(CBr)=CC=C1N1N=CC=C1 PHNRBSHOFSWNII-UHFFFAOYSA-N 0.000 description 1
- CJTZXIJETZZARD-UHFFFAOYSA-N 1-iodo-2,2-dimethylpropane Chemical compound CC(C)(C)CI CJTZXIJETZZARD-UHFFFAOYSA-N 0.000 description 1
- DCGGMHIZEAHUJL-UHFFFAOYSA-N 1-methyl-1,3-diazinane-2,4,6-trione Chemical compound CN1C(=O)CC(=O)NC1=O DCGGMHIZEAHUJL-UHFFFAOYSA-N 0.000 description 1
- SNTWKPAKVQFCCF-UHFFFAOYSA-N 2,3-dihydro-1h-triazole Chemical compound N1NC=CN1 SNTWKPAKVQFCCF-UHFFFAOYSA-N 0.000 description 1
- VOHILFSOWRNVJJ-UHFFFAOYSA-N 2-(bromomethyl)oxolane Chemical compound BrCC1CCCO1 VOHILFSOWRNVJJ-UHFFFAOYSA-N 0.000 description 1
- NPSCUAAYKNARMG-UHFFFAOYSA-N 2-[4-(bromomethyl)phenyl]-5-fluoropyrimidine Chemical compound N1=CC(F)=CN=C1C1=CC=C(CBr)C=C1 NPSCUAAYKNARMG-UHFFFAOYSA-N 0.000 description 1
- FCLQGHNSQXFQEG-UHFFFAOYSA-N 2-[4-(bromomethyl)phenyl]pyridine Chemical compound C1=CC(CBr)=CC=C1C1=CC=CC=N1 FCLQGHNSQXFQEG-UHFFFAOYSA-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
- MFRUVSDIZTZFFL-UHFFFAOYSA-N 2-bromo-n,n-dimethylethanamine;hydrobromide Chemical compound [Br-].C[NH+](C)CCBr MFRUVSDIZTZFFL-UHFFFAOYSA-N 0.000 description 1
- NUGDPTDTOCLGNC-UHFFFAOYSA-N 3-anilino-2-[[4-(5-fluoropyrimidin-2-yl)phenyl]methyl]-5-methyl-7-(2-methylpropyl)pyrazolo[3,4-d]pyrimidine-4,6-dione Chemical compound C=1C=CC=CC=1NC1=C2C(=O)N(C)C(=O)N(CC(C)C)C2=NN1CC(C=C1)=CC=C1C1=NC=C(F)C=N1 NUGDPTDTOCLGNC-UHFFFAOYSA-N 0.000 description 1
- DNJRIARNJBYOJD-UHFFFAOYSA-N 3-anilino-5-methyl-7-(2-methylpropyl)-2-[[4-(1,2,4-triazol-1-yl)phenyl]methyl]pyrazolo[3,4-d]pyrimidine-4,6-dione Chemical compound C=1C=CC=CC=1NC1=C2C(=O)N(C)C(=O)N(CC(C)C)C2=NN1CC(C=C1)=CC=C1N1C=NC=N1 DNJRIARNJBYOJD-UHFFFAOYSA-N 0.000 description 1
- HRUIRVYTAXOBQV-UHFFFAOYSA-N 3-anilino-7-[2-(dimethylamino)ethyl]-5-methyl-2-[(4-pyridin-2-ylphenyl)methyl]pyrazolo[3,4-d]pyrimidine-4,6-dione Chemical compound C=1C=CC=CC=1NC1=C2C(=O)N(C)C(=O)N(CCN(C)C)C2=NN1CC(C=C1)=CC=C1C1=CC=CC=N1 HRUIRVYTAXOBQV-UHFFFAOYSA-N 0.000 description 1
- OVILZFVTUVWJTO-UHFFFAOYSA-N 4-(chloromethyl)benzamide Chemical compound NC(=O)C1=CC=C(CCl)C=C1 OVILZFVTUVWJTO-UHFFFAOYSA-N 0.000 description 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 1
- IRQUWHXXVJARBK-UHFFFAOYSA-N 5-(bromomethyl)-2-(trifluoromethyl)pyridine Chemical compound FC(F)(F)C1=CC=C(CBr)C=N1 IRQUWHXXVJARBK-UHFFFAOYSA-N 0.000 description 1
- RGTBLCLLSZPOKR-UHFFFAOYSA-N 5-methyl-1,2,4-oxadiazole Chemical compound CC1=NC=NO1 RGTBLCLLSZPOKR-UHFFFAOYSA-N 0.000 description 1
- MCYCQJQSPPXMIE-UHFFFAOYSA-N 5-methyl-7-(2-methylpropyl)-1h-pyrazolo[3,4-d]pyrimidine-4,6-dione Chemical compound O=C1N(C)C(=O)N(CC(C)C)C2=NNC=C21 MCYCQJQSPPXMIE-UHFFFAOYSA-N 0.000 description 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- AEOBEOJCBAYXBA-UHFFFAOYSA-N A2P5P Natural products C1=NC=2C(N)=NC=NC=2N1C1OC(COP(O)(O)=O)C(O)C1OP(O)(O)=O AEOBEOJCBAYXBA-UHFFFAOYSA-N 0.000 description 1
- 206010000234 Abortion spontaneous Diseases 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- GTNLLOVZWNHZPG-UHFFFAOYSA-N C1(=CC=CC=C1)NN1N=C2NC(NC(C2=C1)=O)=O Chemical compound C1(=CC=CC=C1)NN1N=C2NC(NC(C2=C1)=O)=O GTNLLOVZWNHZPG-UHFFFAOYSA-N 0.000 description 1
- 101100243082 Caenorhabditis elegans pde-1 gene Proteins 0.000 description 1
- 102000004631 Calcineurin Human genes 0.000 description 1
- 108010042955 Calcineurin Proteins 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- 102000014914 Carrier Proteins Human genes 0.000 description 1
- 102100040999 Catechol O-methyltransferase Human genes 0.000 description 1
- 108020002739 Catechol O-methyltransferase Proteins 0.000 description 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 description 1
- 101710095468 Cyclase Proteins 0.000 description 1
- 102000005636 Cyclic AMP Response Element-Binding Protein Human genes 0.000 description 1
- 108010045171 Cyclic AMP Response Element-Binding Protein Proteins 0.000 description 1
- HCYAFALTSJYZDH-UHFFFAOYSA-N Desimpramine Chemical compound C1CC2=CC=CC=C2N(CCCNC)C2=CC=CC=C21 HCYAFALTSJYZDH-UHFFFAOYSA-N 0.000 description 1
- 102000018899 Glutamate Receptors Human genes 0.000 description 1
- 108010027915 Glutamate Receptors Proteins 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- DUGOZIWVEXMGBE-UHFFFAOYSA-N Methylphenidate Chemical compound C=1C=CC=CC=1C(C(=O)OC)C1CCCCN1 DUGOZIWVEXMGBE-UHFFFAOYSA-N 0.000 description 1
- 102000010909 Monoamine Oxidase Human genes 0.000 description 1
- 108010062431 Monoamine oxidase Proteins 0.000 description 1
- 101000909851 Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv) cAMP/cGMP dual specificity phosphodiesterase Rv0805 Proteins 0.000 description 1
- XGEGHDBEHXKFPX-UHFFFAOYSA-N N-methylthiourea Natural products CNC(N)=O XGEGHDBEHXKFPX-UHFFFAOYSA-N 0.000 description 1
- 101100079800 Nicotiana langsdorffii x Nicotiana sanderae NECI gene Proteins 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 102000007982 Phosphoproteins Human genes 0.000 description 1
- 108010089430 Phosphoproteins Proteins 0.000 description 1
- 108091000080 Phosphotransferase Proteins 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 206010062519 Poor quality sleep Diseases 0.000 description 1
- 206010036600 Premature labour Diseases 0.000 description 1
- 208000006011 Stroke Diseases 0.000 description 1
- 108010037572 Type 1 Cyclic Nucleotide Phosphodiesterases Proteins 0.000 description 1
- 102000010856 Type 1 Cyclic Nucleotide Phosphodiesterases Human genes 0.000 description 1
- 206010000210 abortion Diseases 0.000 description 1
- 231100000176 abortion Toxicity 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- UDMBCSSLTHHNCD-KQYNXXCUSA-N adenosine 5'-monophosphate Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O UDMBCSSLTHHNCD-KQYNXXCUSA-N 0.000 description 1
- 239000000556 agonist Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000006307 alkoxy benzyl group Chemical group 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 239000002269 analeptic agent Substances 0.000 description 1
- 229940065524 anticholinergics inhalants for obstructive airway diseases Drugs 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000005002 aryl methyl group Chemical group 0.000 description 1
- 238000003149 assay kit Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 125000002619 bicyclic group Chemical group 0.000 description 1
- 108091008324 binding proteins Proteins 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 210000004958 brain cell Anatomy 0.000 description 1
- 210000005013 brain tissue Anatomy 0.000 description 1
- 125000005997 bromomethyl group Chemical group 0.000 description 1
- LRHPLDYGYMQRHN-UHFFFAOYSA-N butyl alcohol Substances CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 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
- 239000002775 capsule Substances 0.000 description 1
- QTAOMKOIBXZKND-PPHPATTJSA-N carbidopa Chemical compound O.NN[C@@](C(O)=O)(C)CC1=CC=C(O)C(O)=C1 QTAOMKOIBXZKND-PPHPATTJSA-N 0.000 description 1
- 229960004205 carbidopa Drugs 0.000 description 1
- 230000030833 cell death Effects 0.000 description 1
- 210000000782 cerebellar granule cell Anatomy 0.000 description 1
- XMPZTFVPEKAKFH-UHFFFAOYSA-P ceric ammonium nitrate Chemical compound [NH4+].[NH4+].[Ce+4].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O XMPZTFVPEKAKFH-UHFFFAOYSA-P 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 239000000812 cholinergic antagonist Substances 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 229960004606 clomipramine Drugs 0.000 description 1
- 230000003920 cognitive function Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 210000001947 dentate gyrus Anatomy 0.000 description 1
- 229960003914 desipramine Drugs 0.000 description 1
- 229960000632 dexamfetamine Drugs 0.000 description 1
- 125000002720 diazolyl group Chemical group 0.000 description 1
- 208000037765 diseases and disorders Diseases 0.000 description 1
- 239000000510 dopamine 1 receptor stimulating agent Substances 0.000 description 1
- 229940052760 dopamine agonists Drugs 0.000 description 1
- 230000008923 dopaminergic innervation Effects 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000012636 effector Substances 0.000 description 1
- 235000013601 eggs Nutrition 0.000 description 1
- 210000004696 endometrium Anatomy 0.000 description 1
- 238000001952 enzyme assay Methods 0.000 description 1
- 239000003687 estradiol congener Substances 0.000 description 1
- 230000012173 estrus Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229960002464 fluoxetine Drugs 0.000 description 1
- 235000013928 guanylic acid Nutrition 0.000 description 1
- 208000019622 heart disease Diseases 0.000 description 1
- 125000000592 heterocycloalkyl group Chemical group 0.000 description 1
- 210000001320 hippocampus Anatomy 0.000 description 1
- 229940088597 hormone Drugs 0.000 description 1
- 239000005556 hormone Substances 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 229960004801 imipramine Drugs 0.000 description 1
- BCGWQEUPMDMJNV-UHFFFAOYSA-N imipramine Chemical compound C1CC2=CC=CC=C2N(CCCN(C)C)C2=CC=CC=C21 BCGWQEUPMDMJNV-UHFFFAOYSA-N 0.000 description 1
- 230000028993 immune response Effects 0.000 description 1
- 238000002513 implantation Methods 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 230000037041 intracellular level Effects 0.000 description 1
- FUCOMWZKWIEKRK-UHFFFAOYSA-N iodocyclohexane Chemical compound IC1CCCCC1 FUCOMWZKWIEKRK-UHFFFAOYSA-N 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 230000006742 locomotor activity Effects 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000013011 mating Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 230000002175 menstrual effect Effects 0.000 description 1
- 229960001252 methamphetamine Drugs 0.000 description 1
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- 229960001344 methylphenidate Drugs 0.000 description 1
- XGEGHDBEHXKFPX-NJFSPNSNSA-N methylurea Chemical compound [14CH3]NC(N)=O XGEGHDBEHXKFPX-NJFSPNSNSA-N 0.000 description 1
- 208000015994 miscarriage Diseases 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 210000002464 muscle smooth vascular Anatomy 0.000 description 1
- 208000010125 myocardial infarction Diseases 0.000 description 1
- 210000004165 myocardium Anatomy 0.000 description 1
- 230000004770 neurodegeneration Effects 0.000 description 1
- 208000015122 neurodegenerative disease Diseases 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000002773 nucleotide Substances 0.000 description 1
- 125000003729 nucleotide group Chemical group 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 210000001706 olfactory mucosa Anatomy 0.000 description 1
- 210000002475 olfactory pathway Anatomy 0.000 description 1
- 239000006186 oral dosage form Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229960000761 pemoline Drugs 0.000 description 1
- NRNCYVBFPDDJNE-UHFFFAOYSA-N pemoline Chemical compound O1C(N)=NC(=O)C1C1=CC=CC=C1 NRNCYVBFPDDJNE-UHFFFAOYSA-N 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 1
- 102000020233 phosphotransferase Human genes 0.000 description 1
- 230000004962 physiological condition Effects 0.000 description 1
- 230000010287 polarization Effects 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 230000035935 pregnancy Effects 0.000 description 1
- 208000026440 premature labor Diseases 0.000 description 1
- 150000003146 progesterones Chemical class 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 208000020016 psychiatric disease Diseases 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000000241 respiratory effect Effects 0.000 description 1
- 208000023504 respiratory system disease Diseases 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 239000003772 serotonin uptake inhibitor Substances 0.000 description 1
- 229960002073 sertraline Drugs 0.000 description 1
- VGKDLMBJGBXTGI-SJCJKPOMSA-N sertraline Chemical compound C1([C@@H]2CC[C@@H](C3=CC=CC=C32)NC)=CC=C(Cl)C(Cl)=C1 VGKDLMBJGBXTGI-SJCJKPOMSA-N 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 230000001568 sexual effect Effects 0.000 description 1
- 230000036332 sexual response Effects 0.000 description 1
- 230000008054 signal transmission Effects 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 208000000995 spontaneous abortion Diseases 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000006223 tetrahydrofuranylmethyl group Chemical group 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 125000004299 tetrazol-5-yl group Chemical group [H]N1N=NC(*)=N1 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
Classifications
-
- 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
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
-
- 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
-
- 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
- A61P11/02—Nasal agents, e.g. decongestants
-
- 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
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/08—Bronchodilators
-
- 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
- A61P13/08—Drugs for disorders of the urinary system of the prostate
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/08—Drugs for genital or sexual disorders; Contraceptives for gonadal disorders or for enhancing fertility, e.g. inducers of ovulation or of spermatogenesis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/12—Drugs for genital or sexual disorders; Contraceptives for climacteric disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
- A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
-
- 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
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/08—Antiepileptics; Anticonvulsants
-
- 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
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
-
- 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
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- 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
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- 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
- A61P25/20—Hypnotics; Sedatives
-
- 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
- A61P25/22—Anxiolytics
-
- 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
- A61P25/24—Antidepressants
-
- 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
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- 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
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
-
- 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
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A61P25/36—Opioid-abuse
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P39/00—General protective or antinoxious agents
- A61P39/02—Antidotes
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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
- A61P5/14—Drugs for disorders of the endocrine system of the thyroid hormones, e.g. T3, T4
-
- 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
- A61P5/24—Drugs for disorders of the endocrine system of the sex hormones
-
- 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
- A61P5/24—Drugs for disorders of the endocrine system of the sex hormones
- A61P5/32—Antioestrogens
-
- 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
- A61P5/24—Drugs for disorders of the endocrine system of the sex hormones
- A61P5/36—Antigestagens
-
- 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
-
- 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
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- 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
- A61P9/12—Antihypertensives
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Endocrinology (AREA)
- Pulmonology (AREA)
- Immunology (AREA)
- Psychiatry (AREA)
- Reproductive Health (AREA)
- Diabetes (AREA)
- Addiction (AREA)
- Physical Education & Sports Medicine (AREA)
- Rheumatology (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Pain & Pain Management (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Urology & Nephrology (AREA)
- Psychology (AREA)
- Epidemiology (AREA)
- Agronomy & Crop Science (AREA)
- Toxicology (AREA)
- Vascular Medicine (AREA)
- Gynecology & Obstetrics (AREA)
- Pregnancy & Childbirth (AREA)
- Hospice & Palliative Care (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US81168706P | 2006-06-06 | 2006-06-06 | |
| US87318506P | 2006-12-05 | 2006-12-05 | |
| PCT/US2007/070551 WO2007143705A2 (en) | 2006-06-06 | 2007-06-06 | Organic compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| MX2008015489A true MX2008015489A (es) | 2009-01-13 |
Family
ID=38802329
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MX2008015489A MX2008015489A (es) | 2006-06-06 | 2007-06-06 | Compuestos organicos. |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US9255099B2 (https=) |
| EP (1) | EP2023729B1 (https=) |
| JP (2) | JP5453086B2 (https=) |
| KR (1) | KR20090042227A (https=) |
| AU (1) | AU2007256633B2 (https=) |
| CA (1) | CA2651519A1 (https=) |
| MX (1) | MX2008015489A (https=) |
| WO (1) | WO2007143705A2 (https=) |
Families Citing this family (48)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL160307A0 (en) | 2001-08-31 | 2004-07-25 | Univ Rockefeller | Phosphodiesterase activity and regulation of phosphodiesterase 1-b-mediated signaling in brain |
| AU2006255028B2 (en) | 2005-06-06 | 2012-04-19 | Intra-Cellular Therapies, Inc. | Organic compounds |
| US20080194592A1 (en) * | 2005-08-23 | 2008-08-14 | Intra-Cellular Therapies, Inc. | Organic Compounds |
| KR20090042227A (ko) * | 2006-06-06 | 2009-04-29 | 인트라-셀룰라 써래피스, 인코퍼레이티드. | 유기 화합물 |
| WO2008063505A1 (en) * | 2006-11-13 | 2008-05-29 | Intra-Cellular Therapies, Inc. | Organic compounds |
| WO2008070095A1 (en) * | 2006-12-05 | 2008-06-12 | Intra-Cellular Therapies, Inc. | Novel uses |
| EP2240028B1 (en) * | 2007-12-06 | 2016-07-20 | Intra-Cellular Therapies, Inc. | Pyrazolopyrimidine-4,6-dione derivatives and their use as pharmaceutical |
| KR20120012831A (ko) | 2007-12-06 | 2012-02-10 | 인트라-셀룰라 써래피스, 인코퍼레이티드. | 유기 화합물 |
| US20120070443A1 (en) * | 2008-12-02 | 2012-03-22 | University Of Utah Research Foundation | Pde1 as a target therapeutic in heart disease |
| EP2367431B1 (en) * | 2008-12-06 | 2015-08-05 | Intra-Cellular Therapies, Inc. | Organic compounds |
| EP2367430B1 (en) | 2008-12-06 | 2014-08-13 | Intra-Cellular Therapies, Inc. | Organic compounds |
| MA32942B1 (fr) | 2008-12-06 | 2012-01-02 | Intra Cellular Therapies Inc | Composes organiques |
| KR20110103949A (ko) | 2008-12-06 | 2011-09-21 | 인트라-셀룰라 써래피스, 인코퍼레이티드. | 유기 화합물 |
| JP5778582B2 (ja) | 2008-12-06 | 2015-09-16 | イントラ−セルラー・セラピーズ・インコーポレイテッドＩｎｔｒａ−Ｃｅｌｌｕｌａｒ Ｔｈｅｒａｐｉｅｓ， Ｉｎｃ． | 有機化合物 |
| BRPI0922809A2 (pt) * | 2008-12-06 | 2018-05-29 | Intracellular Therapies Inc | compostos orgânicos |
| WO2010098839A1 (en) | 2009-02-25 | 2010-09-02 | Intra-Cellular Therapies, Inc. | Pde 1 inhibitors for ophthalmic disorders |
| JP2012526810A (ja) * | 2009-05-13 | 2012-11-01 | イントラ−セルラー・セラピーズ・インコーポレイテッド | 有機化合物 |
| JP6166534B2 (ja) | 2009-08-05 | 2017-07-19 | イントラ−セルラー・セラピーズ・インコーポレイテッドＩｎｔｒａ−Ｃｅｌｌｕｌａｒ Ｔｈｅｒａｐｉｅｓ， Ｉｎｃ． | 新規調節タンパク質および阻害剤 |
| WO2011043816A1 (en) * | 2009-10-08 | 2011-04-14 | Intra-Cellular Therapies, Inc. | Phosphodiesterase 1-targeting tracers and methods |
| WO2011153135A1 (en) | 2010-05-31 | 2011-12-08 | Intra-Cellular Therapies, Inc. | Organic compounds |
| EP2576551A4 (en) | 2010-05-31 | 2014-04-16 | Intra Cellular Therapies Inc | ORGANIC CONNECTIONS |
| WO2011153136A1 (en) * | 2010-05-31 | 2011-12-08 | Intra-Cellular Therapies, Inc. | Organic compounds |
| TW201206937A (en) | 2010-05-31 | 2012-02-16 | Intra Cellular Therapies Inc | Organic compounds |
| JP6051210B2 (ja) | 2011-06-10 | 2016-12-27 | イントラ−セルラー・セラピーズ・インコーポレイテッドＩｎｔｒａ−Ｃｅｌｌｕｌａｒ Ｔｈｅｒａｐｉｅｓ， Ｉｎｃ． | 有機化合物 |
| CA2877146C (en) | 2012-06-18 | 2020-10-20 | Dart Neuroscience (Cayman) Ltd | Substituted thiophene- and furan-fused azolopyrimidine-5-(6h)-one compounds |
| US9801882B2 (en) | 2013-02-17 | 2017-10-31 | Intra-Cellular Therapies, Inc. | Phosphodiesterase-1 inhibitors and their use in treatment of cardiovascular diseases |
| EP2968338B1 (en) | 2013-03-15 | 2019-01-09 | Intra-Cellular Therapies, Inc. | Pde1 inhibitors for use in the treatment and/or prevention of cns injuries, and pns diseases, disorders or injuries |
| KR102240326B1 (ko) * | 2013-03-15 | 2021-04-13 | 인트라-셀룰라 써래피스, 인코퍼레이티드. | 유기 화합물 |
| JP6696904B2 (ja) | 2014-01-08 | 2020-05-20 | イントラ−セルラー・セラピーズ・インコーポレイテッドＩｎｔｒａ−Ｃｅｌｌｕｌａｒ Ｔｈｅｒａｐｉｅｓ， Ｉｎｃ． | 製剤および医薬組成物 |
| EP3157926B1 (en) | 2014-06-20 | 2019-05-15 | Intra-Cellular Therapies, Inc. | Organic compounds |
| US10131671B2 (en) | 2014-08-07 | 2018-11-20 | Intra-Cellular Therapies, Inc. | Organic compounds |
| US9546175B2 (en) | 2014-08-07 | 2017-01-17 | Intra-Cellular Therapies, Inc. | Organic compounds |
| US10285992B2 (en) | 2014-08-07 | 2019-05-14 | Intra-Cellular Therapies, Inc. | Combinations of PDE1 inhibitors and NEP inhibitors and associated methods |
| CA2961212C (en) | 2014-09-17 | 2024-02-06 | Intra-Cellular Therapies, Inc. | Compounds and methods |
| HK1244427A1 (zh) | 2014-12-06 | 2018-08-10 | Intra-Cellular Therapies, Inc. | 有机化合物 |
| CA2969594A1 (en) | 2014-12-06 | 2016-06-09 | Intra-Cellular Therapies, Inc. | Pde2 inhibiting organic compounds |
| US10682354B2 (en) | 2016-03-28 | 2020-06-16 | Intra-Cellular Therapies, Inc. | Compositions and methods |
| JP7134168B6 (ja) | 2016-09-12 | 2024-02-02 | イントラ－セルラー・セラピーズ・インコーポレイテッド | 新規使用 |
| KR102590848B1 (ko) | 2016-12-28 | 2023-10-19 | 다트 뉴로사이언스, 엘엘씨 | Pde2 억제제로서 치환된 피라졸로피리미디논 화합물 |
| DK3717488T3 (da) | 2017-11-27 | 2021-12-13 | Dart Neuroscience Llc | Substituerede furanopyrimidinforbindelser som pde1-inhibitorer |
| JP7401442B2 (ja) | 2018-01-31 | 2023-12-19 | イントラ－セルラー・セラピーズ・インコーポレイテッド | 新規使用 |
| MX2020012628A (es) | 2018-05-25 | 2021-01-29 | Intra Cellular Therapies Inc | Compuestos organicos. |
| US20210338679A1 (en) | 2018-09-25 | 2021-11-04 | Intra-Cellular Therapies, Inc. | Novel uses |
| US11628171B2 (en) | 2019-03-13 | 2023-04-18 | Children's Medical Center Corporation | Method for treating brain or nerve injury |
| WO2020210614A1 (en) | 2019-04-12 | 2020-10-15 | Intra-Cellular Therapies, Inc. | Organic compounds |
| CN110483416A (zh) * | 2019-08-22 | 2019-11-22 | 苏州汉德创宏生化科技有限公司 | 6-氯-3-烷基尿嘧啶的合成方法 |
| EP4413980A3 (en) | 2019-09-03 | 2024-10-30 | Intra-Cellular Therapies, Inc. | Novel compounds |
| US12364695B2 (en) | 2020-06-02 | 2025-07-22 | Intra-Cellular Therapies, Inc. | Methods of treating inflammatory disease |
Family Cites Families (79)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3689863A (en) * | 1969-12-08 | 1972-09-05 | Matsushita Electric Industrial Co Ltd | Voltage dependent resistors in a surface barrier type |
| US3801962A (en) | 1972-12-29 | 1974-04-02 | Ibm | Communication mechanism for data transfer and control between data processing systems and subsystems |
| GB1447426A (en) | 1974-03-20 | 1976-08-25 | Lepetit Spa | Pyrrolo 3,4-d- pyrimidines and methods for their preparation |
| JPS6032638B2 (ja) * | 1976-09-01 | 1985-07-29 | 武田薬品工業株式会社 | ３−アミノピラゾロ〔３，４−ｄ〕ピリミジン誘導体 |
| EP0077372A1 (de) | 1981-04-22 | 1983-04-27 | Byk Gulden Lomberg Chemische Fabrik GmbH | NEUE PYRAZOLO(3,4-d)PYRIMIDINE, VERFAHREN ZU DEREN HERSTELLUNG UND SIE ENTHALTENDE ARZNEIMITTEL |
| US4603203A (en) | 1983-12-14 | 1986-07-29 | Takeda Chemical Industries, Ltd. | 3-aminopyrazolo[3,4-d]pyrimidine derivatives and production thereof |
| US4663326A (en) | 1985-04-04 | 1987-05-05 | Warner-Lambert Company | Pyrazolo[4,3-d]pyrimidine-5,7-(4H,6H)dione or -5-thione-7-one analogs |
| US4666908A (en) | 1985-04-05 | 1987-05-19 | Warner-Lambert Company | 5-Substituted pyrazolo[4,3-d]pyrimidine-7-ones and methods of use |
| JPS6310788A (ja) * | 1986-03-14 | 1988-01-18 | Takeda Chem Ind Ltd | ３−アミノピラゾロ〔３，４−ｄ〕ピリミジン誘導体 |
| EP0237289A3 (en) | 1986-03-14 | 1988-07-27 | Takeda Chemical Industries, Ltd. | Pyrazolo [3,4-d] pyrimidine derivatives, their production and use |
| US4912104A (en) | 1987-08-31 | 1990-03-27 | Takeda Chemical Industries, Ltd. | Tricyclic fused pryimidine derivatives, and their use as pharmaceuticals |
| JPH01265027A (ja) | 1988-04-14 | 1989-10-23 | Takeda Chem Ind Ltd | 肝疾患治療剤 |
| EP0353941A3 (en) | 1988-08-02 | 1991-05-02 | Takeda Chemical Industries, Ltd. | Medicament for psoriasis containing derivatives of 3-aminopyrazolo [3,4-d]pyrimidine |
| JP3116230B2 (ja) | 1989-02-15 | 2000-12-11 | 武田薬品工業株式会社 | 三環式縮合ピリミジン誘導体 |
| JPH02289518A (ja) | 1989-02-15 | 1990-11-29 | Takeda Chem Ind Ltd | アデノシン拮抗剤 |
| KR920004437B1 (ko) | 1989-09-12 | 1992-06-05 | 삼성전자 주식회사 | 금전등록기의 거래선 관리방법 |
| US5250534A (en) * | 1990-06-20 | 1993-10-05 | Pfizer Inc. | Pyrazolopyrimidinone antianginal agents |
| NZ238609A (en) | 1990-06-21 | 1993-12-23 | Schering Corp | Polycyclic guanine derivatives; preparation, pharmaceutical compositions, |
| ES2148170T3 (es) | 1990-12-21 | 2000-10-16 | Beecham Group Plc | Derivados de xantina. |
| US5202328A (en) | 1991-03-06 | 1993-04-13 | Merck & Co., Inc. | Substituted fused pyrimidinones |
| US5223501A (en) | 1991-05-10 | 1993-06-29 | Merck & Co., Inc. | Substituted pyrimidinones bearing acidic functional groups as angiotensin ii antagonists |
| US5294612A (en) * | 1992-03-30 | 1994-03-15 | Sterling Winthrop Inc. | 6-heterocyclyl pyrazolo [3,4-d]pyrimidin-4-ones and compositions and method of use thereof |
| US5939419A (en) * | 1993-02-26 | 1999-08-17 | Schering-Plough Corporation | 2-benzyl-polycyclic guanine derivatives and process for preparing them |
| US5656629A (en) | 1995-03-10 | 1997-08-12 | Sanofi Winthrop, Inc. | 6-substituted pyrazolo (3,4-d)pyrimidin-4-ones and compositions and methods of use thereof |
| IT1277392B1 (it) | 1995-07-28 | 1997-11-10 | Schering Plough S P A | Analoghi eterociclici di 1,2,4-triazolo(1,5-c]pirimidine ad attivita' antagonista per il recettore a2a dell'adenosina |
| GB9626643D0 (en) | 1996-12-21 | 1997-02-12 | Astra Pharma Prod | Compounds |
| DE19709126A1 (de) | 1997-03-06 | 1998-09-10 | Bayer Ag | Arylamin-, -oxy-, -thio-substituierte Dihydropurinone und Pyrazolopyrimidine |
| SE9701398D0 (sv) | 1997-04-15 | 1997-04-15 | Astra Pharma Prod | Novel compounds |
| IT1291372B1 (it) | 1997-05-21 | 1999-01-07 | Schering Plough S P A | Uso di analoghi eterociclici di 1,2,4-triazolo (1,5-c) pirimidine per la preparazione di medicamenti utili per il trattamento delle malattie |
| GB9722520D0 (en) | 1997-10-24 | 1997-12-24 | Pfizer Ltd | Compounds |
| US6133273A (en) * | 1998-05-08 | 2000-10-17 | American Home Products Corporation | Pyrazolopyrimidine-2,4-dione sulfonamides |
| US6166019A (en) | 1998-07-16 | 2000-12-26 | Abbott Laboratories | Piperazinyl pyrimidine dione compounds selective for adrenoceptors |
| DE19931206A1 (de) | 1999-07-07 | 2001-01-11 | Stief Christian | Arzneimittel zur Erhöhung des cAMP-Spiegels und deren Verwendung |
| HK1049834A1 (zh) * | 1999-10-11 | 2003-05-30 | 辉瑞大药厂 | 用作磷酸二酯酶抑制剂的5-(2-取代的-5-杂环基磺酰基吡啶-3-基)-二氢吡唑并[4，3-d]嘧啶-7-酮类化合物 |
| TWI265925B (en) | 1999-10-11 | 2006-11-11 | Pfizer | Pyrazolo[4,3-d]pyrimidin-7-ones useful in inhibiting type 5 cyclic guanosine 3',5'-monophosphate phosphodiesterases(cGMP PDE5), process and intermediates for their preparation, their uses and composition comprising them |
| IL139073A0 (en) * | 1999-10-21 | 2001-11-25 | Pfizer | Treatment of neuropathy |
| IL139457A0 (en) | 1999-11-08 | 2001-11-25 | Pfizer | Compounds for the treatment of female sexual dysfunction |
| MY125533A (en) | 1999-12-06 | 2006-08-30 | Bristol Myers Squibb Co | Heterocyclic dihydropyrimidine compounds |
| US20020006926A1 (en) * | 2000-04-19 | 2002-01-17 | Roylance H. H. | Use of cyclic GMP-specific phosphodiesterase inhibitors for treatment of parkinson's disease |
| WO2002074312A1 (en) | 2001-03-16 | 2002-09-26 | Pfizer Limited | Pyrazolo`4,3-d.pyrimidinone compounds as cgmp pde inhibitors |
| WO2002088079A2 (en) | 2001-05-01 | 2002-11-07 | Bristol-Myers Squibb Company | Dual inhibitors of pde 7 and pde 4 |
| SE0102315D0 (sv) * | 2001-06-28 | 2001-06-28 | Astrazeneca Ab | Compounds |
| IL160307A0 (en) | 2001-08-31 | 2004-07-25 | Univ Rockefeller | Phosphodiesterase activity and regulation of phosphodiesterase 1-b-mediated signaling in brain |
| HN2002000317A (es) | 2001-11-02 | 2003-05-21 | Pfizer | Inhibidores de pde9 para tratamiento de trastornos cardiovasculares |
| DE10238723A1 (de) | 2002-08-23 | 2004-03-11 | Bayer Ag | Phenyl-substituierte Pyrazolyprimidine |
| GB0230045D0 (en) | 2002-12-23 | 2003-01-29 | Glaxo Group Ltd | Compounds |
| SE0203825D0 (sv) | 2002-12-20 | 2002-12-20 | Astrazeneca Ab | Novel fused heterocycles and uses thereof |
| US20050048573A1 (en) * | 2003-02-03 | 2005-03-03 | Plexxikon, Inc. | PDE5A crystal structure and uses |
| EP1613747A1 (en) | 2003-03-31 | 2006-01-11 | Pfizer Products Inc. | Crystal structure of 3 ,5 -cyclic nucleotide phosphodiesterase 1b (pde1b) and uses thereof |
| US7153824B2 (en) * | 2003-04-01 | 2006-12-26 | Applied Research Systems Ars Holding N.V. | Inhibitors of phosphodiesterases in infertility |
| US7247639B2 (en) * | 2003-06-06 | 2007-07-24 | Endacea, Inc. | A1 adenosine receptor antagonists |
| US7557113B2 (en) | 2003-08-26 | 2009-07-07 | Teijin Pharma Limited | Substituted pyrrolo[3,2-d]pyrimidine derivatives |
| AU2006255028B2 (en) | 2005-06-06 | 2012-04-19 | Intra-Cellular Therapies, Inc. | Organic compounds |
| US20080194592A1 (en) * | 2005-08-23 | 2008-08-14 | Intra-Cellular Therapies, Inc. | Organic Compounds |
| EP1931668A2 (en) | 2005-09-16 | 2008-06-18 | Ranbaxy Laboratories Limited | Substituted pyrazolo [3,4-b]pyridines as phosphodiesterase inhibitors |
| EP1940389A2 (en) | 2005-10-21 | 2008-07-09 | Braincells, Inc. | Modulation of neurogenesis by pde inhibition |
| EP1852108A1 (en) | 2006-05-04 | 2007-11-07 | Boehringer Ingelheim Pharma GmbH & Co.KG | DPP IV inhibitor formulations |
| KR20090042227A (ko) * | 2006-06-06 | 2009-04-29 | 인트라-셀룰라 써래피스, 인코퍼레이티드. | 유기 화합물 |
| US20070286890A1 (en) | 2006-06-07 | 2007-12-13 | John Garnett Walt | Eyelash applicator and method |
| US20090137549A1 (en) * | 2006-11-09 | 2009-05-28 | Paul John Edward | Novel compounds useful for the treatment of degenerative & inflamatory diseases |
| WO2008063505A1 (en) | 2006-11-13 | 2008-05-29 | Intra-Cellular Therapies, Inc. | Organic compounds |
| WO2008070095A1 (en) | 2006-12-05 | 2008-06-12 | Intra-Cellular Therapies, Inc. | Novel uses |
| CL2008002427A1 (es) | 2007-08-16 | 2009-09-11 | Boehringer Ingelheim Int | Composicion farmaceutica que comprende 1-cloro-4-(b-d-glucopiranos-1-il)-2-[4-((s)-tetrahidrofurano-3-iloxi)bencil]-benceno combinado con 1-[(4-metilquinazolin-2-il)metil]-3-metil-7-(2-butin-1-il)-8-(3-(r)-aminopiperidin-1-il)xantina; y su uso para tratar diabetes mellitus tipo 2. |
| KR20120012831A (ko) | 2007-12-06 | 2012-02-10 | 인트라-셀룰라 써래피스, 인코퍼레이티드. | 유기 화합물 |
| EP2240028B1 (en) | 2007-12-06 | 2016-07-20 | Intra-Cellular Therapies, Inc. | Pyrazolopyrimidine-4,6-dione derivatives and their use as pharmaceutical |
| CA2723222C (en) | 2008-04-22 | 2013-04-02 | Schering Corporation | Phenyl-substituted 2-imino-3-methyl pyrrolo pyrimidinone compounds as bace-1 inhibitors, compositions, and their use |
| MA32942B1 (fr) | 2008-12-06 | 2012-01-02 | Intra Cellular Therapies Inc | Composes organiques |
| BRPI0922809A2 (pt) | 2008-12-06 | 2018-05-29 | Intracellular Therapies Inc | compostos orgânicos |
| EP2367430B1 (en) | 2008-12-06 | 2014-08-13 | Intra-Cellular Therapies, Inc. | Organic compounds |
| JP5778582B2 (ja) | 2008-12-06 | 2015-09-16 | イントラ−セルラー・セラピーズ・インコーポレイテッドＩｎｔｒａ−Ｃｅｌｌｕｌａｒ Ｔｈｅｒａｐｉｅｓ， Ｉｎｃ． | 有機化合物 |
| EP2367431B1 (en) | 2008-12-06 | 2015-08-05 | Intra-Cellular Therapies, Inc. | Organic compounds |
| KR20110103949A (ko) | 2008-12-06 | 2011-09-21 | 인트라-셀룰라 써래피스, 인코퍼레이티드. | 유기 화합물 |
| JP2012526810A (ja) | 2009-05-13 | 2012-11-01 | イントラ−セルラー・セラピーズ・インコーポレイテッド | 有機化合物 |
| WO2011043816A1 (en) | 2009-10-08 | 2011-04-14 | Intra-Cellular Therapies, Inc. | Phosphodiesterase 1-targeting tracers and methods |
| WO2011153136A1 (en) | 2010-05-31 | 2011-12-08 | Intra-Cellular Therapies, Inc. | Organic compounds |
| TW201206937A (en) | 2010-05-31 | 2012-02-16 | Intra Cellular Therapies Inc | Organic compounds |
| WO2011153135A1 (en) | 2010-05-31 | 2011-12-08 | Intra-Cellular Therapies, Inc. | Organic compounds |
| EP2576551A4 (en) | 2010-05-31 | 2014-04-16 | Intra Cellular Therapies Inc | ORGANIC CONNECTIONS |
| JP6051210B2 (ja) | 2011-06-10 | 2016-12-27 | イントラ−セルラー・セラピーズ・インコーポレイテッドＩｎｔｒａ−Ｃｅｌｌｕｌａｒ Ｔｈｅｒａｐｉｅｓ， Ｉｎｃ． | 有機化合物 |
-
2007
- 2007-06-06 KR KR1020097000115A patent/KR20090042227A/ko not_active Ceased
- 2007-06-06 WO PCT/US2007/070551 patent/WO2007143705A2/en not_active Ceased
- 2007-06-06 AU AU2007256633A patent/AU2007256633B2/en not_active Ceased
- 2007-06-06 CA CA002651519A patent/CA2651519A1/en not_active Abandoned
- 2007-06-06 US US12/303,618 patent/US9255099B2/en active Active
- 2007-06-06 MX MX2008015489A patent/MX2008015489A/es not_active Application Discontinuation
- 2007-06-06 JP JP2009514518A patent/JP5453086B2/ja not_active Expired - Fee Related
- 2007-06-06 EP EP07812042.5A patent/EP2023729B1/en not_active Not-in-force
-
2013
- 2013-09-24 JP JP2013196664A patent/JP2014012729A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| WO2007143705A2 (en) | 2007-12-13 |
| US20100173878A1 (en) | 2010-07-08 |
| AU2007256633A1 (en) | 2007-12-13 |
| EP2023729A2 (en) | 2009-02-18 |
| US9255099B2 (en) | 2016-02-09 |
| JP5453086B2 (ja) | 2014-03-26 |
| KR20090042227A (ko) | 2009-04-29 |
| JP2014012729A (ja) | 2014-01-23 |
| CA2651519A1 (en) | 2007-12-13 |
| WO2007143705A3 (en) | 2008-01-24 |
| JP2009539872A (ja) | 2009-11-19 |
| AU2007256633B2 (en) | 2013-09-12 |
| EP2023729B1 (en) | 2016-05-04 |
| EP2023729A4 (en) | 2010-07-14 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| MX2008015489A (es) | Compuestos organicos. | |
| EP2240028B1 (en) | Pyrazolopyrimidine-4,6-dione derivatives and their use as pharmaceutical | |
| EP2240490B1 (en) | Organic compounds | |
| CN101460058A (zh) | 有机化合物 | |
| AU2013270564A1 (en) | Organic compounds | |
| HK1155905A (en) | Organic compounds | |
| HK1154007A (en) | Organic compounds |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FA | Abandonment or withdrawal |