JP2010511709A5 - - Google Patents
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- Publication number
- JP2010511709A5 JP2010511709A5 JP2009540267A JP2009540267A JP2010511709A5 JP 2010511709 A5 JP2010511709 A5 JP 2010511709A5 JP 2009540267 A JP2009540267 A JP 2009540267A JP 2009540267 A JP2009540267 A JP 2009540267A JP 2010511709 A5 JP2010511709 A5 JP 2010511709A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- imidazo
- phenylmethyl
- aryl
- purine
- 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.)
- Granted
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- -1 N-dialkylamino Inorganic materials 0.000 claims description 27
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 26
- 125000005843 halogen group Chemical group 0.000 claims description 24
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 claims description 20
- 125000001424 substituent group Chemical group 0.000 claims description 9
- 229920006395 saturated elastomer Polymers 0.000 claims description 8
- LMKPHJYTFHAGHK-UHFFFAOYSA-N cyclodrine Chemical compound C1CCCC1(O)C(C(=O)OCCN(CC)CC)C1=CC=CC=C1 LMKPHJYTFHAGHK-UHFFFAOYSA-N 0.000 claims description 7
- OSXKHFTZRHDUJN-UHFFFAOYSA-N N(2),3-ethenoguanine Chemical compound O=C1NC2=NC=CN2C2=C1NC=N2 OSXKHFTZRHDUJN-UHFFFAOYSA-N 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 6
- 125000003003 spiro group Chemical group 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- 125000004043 oxo group Chemical group O=* 0.000 claims description 3
- LMKVVNSEQFWADD-IKLZKGPXSA-N (4S)-5-benzyl-4,8-dimethyl-1,3,5,8,10-pentazatetracyclo[7.6.0.02,6.011,15]pentadeca-12,14-diene-7-thione Chemical compound C[C@H]1NC2N3C(N(C(C2N1CC1=CC=CC=C1)=S)C)NC1C3=CC=C1 LMKVVNSEQFWADD-IKLZKGPXSA-N 0.000 claims description 2
- HTTROEILAAXBHH-MRVPVSSYSA-N (7s)-2,5-dimethyl-7-propan-2-yl-7,8-dihydro-3h-imidazo[2,1-b]purin-4-one Chemical compound C([C@@H](N=1)C(C)C)N2C=1N(C)C(=O)C1=C2N=C(C)N1 HTTROEILAAXBHH-MRVPVSSYSA-N 0.000 claims description 2
- WRIUADNGMJXJRO-UHFFFAOYSA-N 3-benzyl-5,7,7-trimethyl-2-(trifluoromethyl)-8h-imidazo[2,1-b]purin-4-one Chemical compound C1=2C(=O)N(C)C3=NC(C)(C)CN3C=2N=C(C(F)(F)F)N1CC1=CC=CC=C1 WRIUADNGMJXJRO-UHFFFAOYSA-N 0.000 claims description 2
- BJFYUTNMJGGJOQ-UYLHMDRGSA-N C[C@@H]1NC2N3C(N(C(C2N1)=O)C)NC1C3=CC=CC1 Chemical compound C[C@@H]1NC2N3C(N(C(C2N1)=O)C)NC1C3=CC=CC1 BJFYUTNMJGGJOQ-UYLHMDRGSA-N 0.000 claims description 2
- RMXSRFARZCDMQL-OOHRUDITSA-N C[C@H]1NC2N3C(N(C(C2N1CC1=CC=C(C=C1)Br)=O)C)NC1C3=CC=C1 Chemical compound C[C@H]1NC2N3C(N(C(C2N1CC1=CC=C(C=C1)Br)=O)C)NC1C3=CC=C1 RMXSRFARZCDMQL-OOHRUDITSA-N 0.000 claims description 2
- CEVCYARBXMROHU-XVSUJQINSA-N C[C@H]1NC2N3C(N(C(C2N1CC1=CC=C(C=C1)OC)=O)C)NC1C3=CC=C1 Chemical compound C[C@H]1NC2N3C(N(C(C2N1CC1=CC=C(C=C1)OC)=O)C)NC1C3=CC=C1 CEVCYARBXMROHU-XVSUJQINSA-N 0.000 claims description 2
- NUBDLRGGGIDRCR-KOGDIJHLSA-N C[C@H]1NC2N3C(N(C(C2N1CC1=CC=NC=C1)=O)C)NC1C3=CC=C1 Chemical compound C[C@H]1NC2N3C(N(C(C2N1CC1=CC=NC=C1)=O)C)NC1C3=CC=C1 NUBDLRGGGIDRCR-KOGDIJHLSA-N 0.000 claims description 2
- VRZPGEFNPZRJIS-BDAKNGLRSA-N cis-5,6a,7,8,9,9a-hexahydro-2,3,5-trimethylcyclopent[4,5]imidazo[2,1-b]purin-4(3h)-one Chemical compound N12C=3N=C(C)N(C)C=3C(=O)N(C)C2=N[C@H]2[C@@H]1CCC2 VRZPGEFNPZRJIS-BDAKNGLRSA-N 0.000 claims description 2
- 125000002541 furyl group Chemical group 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 2
- 125000006261 methyl amino sulfonyl group Chemical group [H]N(C([H])([H])[H])S(*)(=O)=O 0.000 claims description 2
- 150000004702 methyl esters Chemical class 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims 74
- 125000003118 aryl group Chemical group 0.000 claims 38
- 125000000753 cycloalkyl group Chemical group 0.000 claims 36
- 125000001072 heteroaryl group Chemical group 0.000 claims 28
- 229910052799 carbon Inorganic materials 0.000 claims 25
- 229910052739 hydrogen Inorganic materials 0.000 claims 24
- 239000008194 pharmaceutical composition Substances 0.000 claims 22
- 125000003710 aryl alkyl group Chemical group 0.000 claims 19
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 19
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 18
- 150000001875 compounds Chemical class 0.000 claims 17
- 150000003839 salts Chemical group 0.000 claims 15
- VOPWNXZWBYDODV-UHFFFAOYSA-N Chlorodifluoromethane Chemical compound FC(F)Cl VOPWNXZWBYDODV-UHFFFAOYSA-N 0.000 claims 14
- 125000003545 alkoxy group Chemical group 0.000 claims 14
- 239000001257 hydrogen Substances 0.000 claims 14
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 14
- 229940121836 Phosphodiesterase 1 inhibitor Drugs 0.000 claims 13
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 11
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 10
- 125000004663 dialkyl amino group Chemical group 0.000 claims 10
- 150000001721 carbon Chemical group 0.000 claims 9
- 229910052736 halogen Inorganic materials 0.000 claims 9
- 150000002367 halogens Chemical class 0.000 claims 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 8
- 125000004414 alkyl thio group Chemical group 0.000 claims 7
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 7
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims 7
- 125000004432 carbon atom Chemical group C* 0.000 claims 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims 6
- 125000001188 haloalkyl group Chemical group 0.000 claims 6
- 150000002431 hydrogen Chemical group 0.000 claims 6
- 229910052757 nitrogen Inorganic materials 0.000 claims 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 5
- LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 claims 5
- 125000004423 acyloxy group Chemical group 0.000 claims 5
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 5
- 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 4
- 125000003282 alkyl amino group Chemical group 0.000 claims 4
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 4
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims 4
- 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 4
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims 4
- 201000010099 disease Diseases 0.000 claims 4
- 208000035475 disorder Diseases 0.000 claims 4
- 125000006682 monohaloalkyl group Chemical group 0.000 claims 4
- 125000006684 polyhaloalkyl group Polymers 0.000 claims 4
- 125000004076 pyridyl group Chemical group 0.000 claims 4
- 125000001113 thiadiazolyl group Chemical group 0.000 claims 4
- 125000001769 aryl amino group Chemical group 0.000 claims 3
- 125000005110 aryl thio group Chemical group 0.000 claims 3
- 125000004104 aryloxy group Chemical group 0.000 claims 3
- 125000002619 bicyclic group Chemical group 0.000 claims 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 3
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 3
- 229940011871 estrogen Drugs 0.000 claims 3
- 239000000262 estrogen Substances 0.000 claims 3
- 125000005241 heteroarylamino group Chemical group 0.000 claims 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 3
- VILOVKQUBCFZCP-UHFFFAOYSA-N 2,5,7,7,8-pentamethyl-3,8-dihydroimidazo[2,1-b]purin-4-one Chemical compound N=1C(C)(C)C(C)N2C=1N(C)C(=O)C1=C2N=C(C)N1 VILOVKQUBCFZCP-UHFFFAOYSA-N 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- 125000005122 aminoalkylamino group Chemical group 0.000 claims 2
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 2
- 125000005129 aryl carbonyl group Chemical group 0.000 claims 2
- 150000001540 azides Chemical class 0.000 claims 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 2
- 125000004438 haloalkoxy group Chemical group 0.000 claims 2
- 125000005114 heteroarylalkoxy group Chemical group 0.000 claims 2
- 125000005223 heteroarylcarbonyl group Chemical group 0.000 claims 2
- 229940088597 hormone Drugs 0.000 claims 2
- 239000005556 hormone Substances 0.000 claims 2
- 125000005191 hydroxyalkylamino group Chemical group 0.000 claims 2
- 230000009245 menopause Effects 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- 239000000186 progesterone Substances 0.000 claims 2
- 229960003387 progesterone Drugs 0.000 claims 2
- 229940124530 sulfonamide Drugs 0.000 claims 2
- 150000003573 thiols Chemical class 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- 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 1
- ZFIXLLHBDJAIIF-VAJTXYMYSA-N (4R)-5-benzyl-4,8-dimethyl-1,3,5,8,10-pentazatetracyclo[7.6.0.02,6.011,15]pentadeca-12,14-dien-7-one Chemical compound C[C@@H]1NC2N3C(N(C(C2N1CC1=CC=CC=C1)=O)C)NC1C3=CC=C1 ZFIXLLHBDJAIIF-VAJTXYMYSA-N 0.000 claims 1
- HTTROEILAAXBHH-QMMMGPOBSA-N (7r)-2,5-dimethyl-7-propan-2-yl-7,8-dihydro-3h-imidazo[2,1-b]purin-4-one Chemical compound C([C@H](N=1)C(C)C)N2C=1N(C)C(=O)C1=C2N=C(C)N1 HTTROEILAAXBHH-QMMMGPOBSA-N 0.000 claims 1
- NVRVNEBAXHEDFJ-LJQANCHMSA-N (7r)-3,7-dibenzyl-2,5-dimethyl-7,8-dihydroimidazo[2,1-b]purin-4-one Chemical compound C([C@H]1N=C2N(C(C=3N(CC=4C=CC=CC=4)C(C)=NC=3N2C1)=O)C)C1=CC=CC=C1 NVRVNEBAXHEDFJ-LJQANCHMSA-N 0.000 claims 1
- IEPMPAZHBXLCOP-LLVKDONJSA-N (7r)-3-benzyl-2,5,7-trimethyl-7,8-dihydroimidazo[2,1-b]purin-4-one Chemical compound C([C@H](N=1)C)N2C=1N(C)C(=O)C1=C2N=C(C)N1CC1=CC=CC=C1 IEPMPAZHBXLCOP-LLVKDONJSA-N 0.000 claims 1
- UGTHPHLZFMDADA-MRXNPFEDSA-N (7r)-3-benzyl-2,5-dimethyl-7-(2-methylpropyl)-7,8-dihydroimidazo[2,1-b]purin-4-one Chemical compound C([C@H](N=1)CC(C)C)N2C=1N(C)C(=O)C1=C2N=C(C)N1CC1=CC=CC=C1 UGTHPHLZFMDADA-MRXNPFEDSA-N 0.000 claims 1
- UKYVGPSNGAZSMN-SFHVURJKSA-N (7r)-3-benzyl-2,5-dimethyl-7-phenyl-7,8-dihydroimidazo[2,1-b]purin-4-one Chemical compound C([C@H](N=C1N(C(C=23)=O)C)C=4C=CC=CC=4)N1C=2N=C(C)N3CC1=CC=CC=C1 UKYVGPSNGAZSMN-SFHVURJKSA-N 0.000 claims 1
- LPWLBWDFJZDWEX-HNNXBMFYSA-N (7r)-3-benzyl-2,5-dimethyl-7-propan-2-yl-7,8-dihydroimidazo[2,1-b]purin-4-one Chemical compound C([C@H](N=1)C(C)C)N2C=1N(C)C(=O)C1=C2N=C(C)N1CC1=CC=CC=C1 LPWLBWDFJZDWEX-HNNXBMFYSA-N 0.000 claims 1
- LPWLBWDFJZDWEX-OAHLLOKOSA-N (7s)-3-benzyl-2,5-dimethyl-7-propan-2-yl-7,8-dihydroimidazo[2,1-b]purin-4-one Chemical compound C([C@@H](N=1)C(C)C)N2C=1N(C)C(=O)C1=C2N=C(C)N1CC1=CC=CC=C1 LPWLBWDFJZDWEX-OAHLLOKOSA-N 0.000 claims 1
- DOWZFRHFNTWIRI-FQNRMIAFSA-N (7s)-3-benzyl-7-butan-2-yl-2,5-dimethyl-7,8-dihydroimidazo[2,1-b]purin-4-one Chemical compound C([C@@H](N=1)C(C)CC)N2C=1N(C)C(=O)C1=C2N=C(C)N1CC1=CC=CC=C1 DOWZFRHFNTWIRI-FQNRMIAFSA-N 0.000 claims 1
- 125000002861 (C1-C4) alkanoyl group Chemical group 0.000 claims 1
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 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 1
- AVUXINBHZQJDEL-UHFFFAOYSA-N 2,5,7,7-tetramethyl-3,8-dihydroimidazo[2,1-b]purin-4-one Chemical compound O=C1N(C)C2=NC(C)(C)CN2C2=C1NC(C)=N2 AVUXINBHZQJDEL-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- YYYNZFNCEJVVKL-UHFFFAOYSA-N 3-benzyl-2,5-dimethyl-7-propyl-7,8-dihydroimidazo[2,1-b]purin-4-one Chemical compound N=1C(CCC)CN2C=1N(C)C(=O)C1=C2N=C(C)N1CC1=CC=CC=C1 YYYNZFNCEJVVKL-UHFFFAOYSA-N 0.000 claims 1
- WFJGMVOWVZKNLA-UHFFFAOYSA-N 3-benzyl-5-methyl-7,8-dihydroimidazo[2,1-b]purin-4-one Chemical compound C1=2C(=O)N(C)C3=NCCN3C=2N=CN1CC1=CC=CC=C1 WFJGMVOWVZKNLA-UHFFFAOYSA-N 0.000 claims 1
- PAIMQQBUPHMLIS-UHFFFAOYSA-N 3-benzyl-5-methyl-8,9-dihydro-7h-pyrimido[2,1-b]purin-4-one Chemical compound N12CCCN=C2N(C)C(=O)C2=C1N=CN2CC1=CC=CC=C1 PAIMQQBUPHMLIS-UHFFFAOYSA-N 0.000 claims 1
- PNWOWTKHERLXTQ-UHFFFAOYSA-N 3-benzyl-5-methyl-8-phenyl-7,8-dihydroimidazo[2,1-b]purin-4-one Chemical compound C1=2C(=O)N(C)C3=NCC(C=4C=CC=CC=4)N3C=2N=CN1CC1=CC=CC=C1 PNWOWTKHERLXTQ-UHFFFAOYSA-N 0.000 claims 1
- DCFKJGKOPGOTIK-UHFFFAOYSA-N 3-benzyl-5-methylspiro[7h-imidazo[2,1-b]purine-8,1'-cyclohexane]-4-one Chemical compound N12C=3N=CN(CC=4C=CC=CC=4)C=3C(=O)N(C)C2=NCC21CCCCC2 DCFKJGKOPGOTIK-UHFFFAOYSA-N 0.000 claims 1
- VPTYAXRMVTVLAL-UHFFFAOYSA-N 3-benzyl-7-ethyl-2,5-dimethyl-7,8-dihydroimidazo[2,1-b]purin-4-one Chemical compound N=1C(CC)CN2C=1N(C)C(=O)C1=C2N=C(C)N1CC1=CC=CC=C1 VPTYAXRMVTVLAL-UHFFFAOYSA-N 0.000 claims 1
- VMYIZJTYOYPOCT-UHFFFAOYSA-N 5-benzyl-4,8,11-trimethyl-1,3,5,8,10-pentazatetracyclo[7.6.0.02,6.011,15]pentadeca-2(6),3,9-trien-7-one Chemical compound C1=2C(=O)N(C)C3=NC4(C)CCCC4N3C=2N=C(C)N1CC1=CC=CC=C1 VMYIZJTYOYPOCT-UHFFFAOYSA-N 0.000 claims 1
- 208000037853 Abnormal uterine bleeding Diseases 0.000 claims 1
- 201000000736 Amenorrhea Diseases 0.000 claims 1
- 206010001928 Amenorrhoea Diseases 0.000 claims 1
- 201000005670 Anovulation Diseases 0.000 claims 1
- 206010002659 Anovulatory cycle Diseases 0.000 claims 1
- 208000023275 Autoimmune disease Diseases 0.000 claims 1
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims 1
- STKXMYWTVCSRLS-UHFFFAOYSA-N CC1N=C2C(=CN(C3=NC4(CCCCC4)CN23)C)N1CC5=CC=CC=C5 Chemical compound CC1N=C2C(=CN(C3=NC4(CCCCC4)CN23)C)N1CC5=CC=CC=C5 STKXMYWTVCSRLS-UHFFFAOYSA-N 0.000 claims 1
- CNVAHKSOYWOKJP-UHFFFAOYSA-N CC1N=C2C(=CN(C3=NCC4(N23)CCCCC4)C)N1CC5=CC=CC=C5 Chemical compound CC1N=C2C(=CN(C3=NCC4(N23)CCCCC4)C)N1CC5=CC=CC=C5 CNVAHKSOYWOKJP-UHFFFAOYSA-N 0.000 claims 1
- UTECHGLOLWYNFQ-PUGIBVIZSA-N CN1[C@@H]2N(C3N(C(N([C@]3(C1=O)C)CC1=CC=CC=C1)(C)C)C)C=CC=N2 Chemical compound CN1[C@@H]2N(C3N(C(N([C@]3(C1=O)C)CC1=CC=CC=C1)(C)C)C)C=CC=N2 UTECHGLOLWYNFQ-PUGIBVIZSA-N 0.000 claims 1
- AKEVCIRHLZCMRV-LUJMMXPNSA-N C[C@@H]1NC2N3C(N(C(C2N1)=O)C)NC1C3=CC=C1 Chemical compound C[C@@H]1NC2N3C(N(C(C2N1)=O)C)NC1C3=CC=C1 AKEVCIRHLZCMRV-LUJMMXPNSA-N 0.000 claims 1
- GNDYBYRTZZQRFE-VCUXHZHDSA-N C[C@@H]1NC2N3C(N(C(C2N1CC1=CC=CC=C1)=O)C)NC1(C3=CCC1)C Chemical compound C[C@@H]1NC2N3C(N(C(C2N1CC1=CC=CC=C1)=O)C)NC1(C3=CCC1)C GNDYBYRTZZQRFE-VCUXHZHDSA-N 0.000 claims 1
- PVMDGNFIHHJTNP-KLUFDXJZSA-N C[C@@H]1NC2N3C(N(C(C2N1CC1=CC=CC=C1)=O)C)NC1C3=CC=CC1 Chemical compound C[C@@H]1NC2N3C(N(C(C2N1CC1=CC=CC=C1)=O)C)NC1C3=CC=CC1 PVMDGNFIHHJTNP-KLUFDXJZSA-N 0.000 claims 1
- GNDYBYRTZZQRFE-JYAUUPNBSA-N C[C@H]1NC2N3C(N(C(C2N1CC1=CC=CC=C1)=O)C)NC1(C3=CCC1)C Chemical compound C[C@H]1NC2N3C(N(C(C2N1CC1=CC=CC=C1)=O)C)NC1(C3=CCC1)C GNDYBYRTZZQRFE-JYAUUPNBSA-N 0.000 claims 1
- ZFIXLLHBDJAIIF-IKLZKGPXSA-N C[C@H]1NC2N3C(N(C(C2N1CC1=CC=CC=C1)=O)C)NC1C3=CC=C1 Chemical compound C[C@H]1NC2N3C(N(C(C2N1CC1=CC=CC=C1)=O)C)NC1C3=CC=C1 ZFIXLLHBDJAIIF-IKLZKGPXSA-N 0.000 claims 1
- FPRBSJYQXZQXMW-JBUCPIAYSA-N C[C@H]1NC2N3C(N(C(C2N1CCN1CCOCC1)=O)C)NC1C3=CC=C1 Chemical compound C[C@H]1NC2N3C(N(C(C2N1CCN1CCOCC1)=O)C)NC1C3=CC=C1 FPRBSJYQXZQXMW-JBUCPIAYSA-N 0.000 claims 1
- PTYRBCFRIXICEH-KZPUIKEJSA-N C[C@H]1NC2N3C(N(C(C2N1COC(C)=O)=O)C)NC1C3=CC=C1 Chemical compound C[C@H]1NC2N3C(N(C(C2N1COC(C)=O)=O)C)NC1C3=CC=C1 PTYRBCFRIXICEH-KZPUIKEJSA-N 0.000 claims 1
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Families Citing this family (58)
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|---|---|---|---|---|
| KR20040066788A (ko) | 2001-08-31 | 2004-07-27 | 더 락커펠러 유니버시티 | 프스포다이에스터레이즈 활성 및 뇌에서프스포다이에스터레이즈 1ｂ 매개되는 신호의 조절 |
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| WO2007025103A2 (en) * | 2005-08-23 | 2007-03-01 | Intra-Cellular Therapies, Inc. | Organic compounds for treating reduced dopamine receptor signalling activity |
| US9255099B2 (en) | 2006-06-06 | 2016-02-09 | Intra-Cellular Therapies, Inc. | Pyrazolo[3,4-D]pyrimidine-4,6(5H,7H)-diones as phosphodiesterase 1 inhibitors |
| EP2081431B1 (en) * | 2006-11-13 | 2013-01-16 | Intra-Cellular Therapies, Inc. | Organic compounds |
| WO2008070095A1 (en) | 2006-12-05 | 2008-06-12 | Intra-Cellular Therapies, Inc. | Novel uses |
| ES2588238T3 (es) * | 2007-12-06 | 2016-10-31 | Intra-Cellular Therapies, Inc. | Derivados de pirazolopirimidin-4,6-diona y su uso como producto farmacéutico |
| CN104370920A (zh) | 2007-12-06 | 2015-02-25 | 武田药品工业株式会社 | 有机化合物 |
| JP5813511B2 (ja) | 2008-12-06 | 2015-11-17 | 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 |
| US8927556B2 (en) | 2008-12-06 | 2015-01-06 | Intra-Cellular Therapies, Inc. | 1H-pyrrolo[3,4-D]pyrimidin-2(6H)-one compounds |
| JP5710493B2 (ja) | 2008-12-06 | 2015-04-30 | 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 |
| ES2638912T3 (es) | 2008-12-06 | 2017-10-24 | Intra-Cellular Therapies, Inc. | Compuestos orgánicos |
| EP2358204B1 (en) * | 2008-12-06 | 2015-08-05 | Intra-Cellular Therapies, Inc. | 4,5,7,8-tetrahydro-4-oxo-2H-imidazo[1,2-a]pyrrolo[3,4-e]pyrimidine compounds as PDE1 inhibitors. |
| US8633180B2 (en) | 2008-12-06 | 2014-01-21 | Intra-Cellular Therapies, Inc. | Organic compounds |
| JP2012518685A (ja) | 2009-02-25 | 2012-08-16 | イントラ−セルラー・セラピーズ・インコーポレイテッド | 眼障害のためのｐｄｅ１阻害剤 |
| 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 |
| SG178279A1 (en) | 2009-08-05 | 2012-03-29 | Intra Cellular Therapies Inc | Novel regulatory proteins and inhibitors |
| US8858911B2 (en) | 2009-10-08 | 2014-10-14 | Intra-Cellular Therapies, Inc. | Phosphodiesterase 1-targeting tracers and methods |
| EP2576551A4 (en) | 2010-05-31 | 2014-04-16 | Intra Cellular Therapies Inc | ORGANIC CONNECTIONS |
| EP2575817A4 (en) * | 2010-05-31 | 2014-01-08 | Intra Cellular Therapies Inc | ORGANIC CONNECTIONS |
| WO2011153135A1 (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 |
| US10561656B2 (en) | 2011-06-10 | 2020-02-18 | Intra-Cellular Therapies, Inc. | Organic compounds |
| AR091507A1 (es) | 2012-06-21 | 2015-02-11 | Intra Cellular Therapies Inc | SALES DE (6aR,9aS)-5,6a,7,8,9,9a-HEXAHIDRO-5-METIL-3-(FENILAMINO)-2-((4-(6-FLUOROPIRIDIN-2-IL)FENIL)METIL)-CICLOPENT[4,5]IMIDAZO[1,2-a]PIRAZOLO[4,3-e]PIRIMIDIN-4(2H)-ONA |
| WO2014127331A1 (en) | 2013-02-17 | 2014-08-21 | Intra-Cellular Therapies, Inc. | Novel uses |
| US9598426B2 (en) | 2013-03-15 | 2017-03-21 | Intra-Cellular Therapies, Inc. | Organic compounds |
| EP3479825B1 (en) * | 2013-03-15 | 2021-02-17 | Intra-Cellular Therapies, Inc. | Pde1 inhibitors for use in the treatment and/or prevention of cns or pns diseases or disorders |
| EP3702358A1 (en) | 2013-06-21 | 2020-09-02 | Intra-Cellular Therapies, Inc. | Process for preparing salts of a known pde1 inhibitor |
| EP3091983B1 (en) | 2014-01-08 | 2019-10-02 | Intra-Cellular Therapies, Inc. | Pharmaceutical compositions comprising a pde-1 inhibitor and a pde-2 inhibitor |
| WO2015196186A1 (en) | 2014-06-20 | 2015-12-23 | 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 |
| JP6591530B2 (ja) | 2014-08-07 | 2019-10-16 | 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 |
| US9546175B2 (en) | 2014-08-07 | 2017-01-17 | Intra-Cellular Therapies, Inc. | Organic compounds |
| ES2857567T3 (es) | 2014-09-17 | 2021-09-29 | Intra Cellular Therapies Inc | Derivados de 7,8-dihidro-[2h]-imidazo-[1,2-a]pirazolo[4,3-e]pirimidin-4(5h)-ona como inhibidores de fosfodiesterasa 1 (PDE1) para tratar enfermedades, trastornos o lesiones del sistema nervioso central (SNC) |
| TW201629064A (zh) | 2014-10-10 | 2016-08-16 | Ｈ 朗德貝克公司 | 作爲ｐｄｅ１抑制劑之三唑並吡酮 |
| AU2015357498B2 (en) | 2014-12-06 | 2019-09-12 | Intra-Cellular Therapies, Inc. | Organic compounds |
| MX371158B (es) | 2014-12-06 | 2020-01-20 | Intra Cellular Therapies Inc | Compuestos inhibidores de pde2. |
| JO3627B1 (ar) | 2015-04-30 | 2020-08-27 | H Lundbeck As | إيميدازو بيرازينونات على هيئة مثبطات pde1 |
| JP2019510039A (ja) | 2016-03-28 | 2019-04-11 | 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． | 新規組成物および方法 |
| TWI729109B (zh) | 2016-04-12 | 2021-06-01 | 丹麥商Ｈ 朗德貝克公司 | 作爲PDE1抑制劑的1,5-二氫-4H-吡唑并[3,4-d]嘧啶-4-酮和1,5-二氫-4H-吡唑并[4,3-c]吡啶-4-酮 |
| US10034861B2 (en) | 2016-07-04 | 2018-07-31 | H. Lundbeck A/S | 1H-pyrazolo[4,3-b]pyridines as PDE1 inhibitors |
| EP3970719A1 (en) | 2016-09-12 | 2022-03-23 | Intra-Cellular Therapies, Inc. | Pde1 inhibitor for use in a method of treatment or prophylaxis of inflammation and/or an inflammatory disease or disorder |
| EP3529250B1 (en) | 2016-10-18 | 2023-12-06 | H. Lundbeck A/S | Imidazopyrazinones, pyrazolopyrimidinones and pyrazolopyridinones as pde1 inhibitors |
| MA46621A (fr) | 2016-10-28 | 2021-06-02 | H Lundbeck As | Traitements combinés comprenant l'administration d'imidazopyrazinones |
| PT3532064T (pt) | 2016-10-28 | 2020-09-03 | H Lundbeck As | Tratamentos de combinação compreendendo imidazopirazinonas para o tratamento de distúrbios psiquiátricos e/ou cognitivos |
| JOP20190126A1 (ar) | 2016-12-22 | 2019-05-28 | H Lundbeck As | بيرازولو [3، 4-b] بيريدينات وإيميدازو [1، 5-b] بيريدازينات على هيئة مثبطات PDE1 |
| WO2018125810A1 (en) | 2016-12-28 | 2018-07-05 | Dart Neuroscience, Llc | Substituted pyrazolopyrimidinone compounds as pde2 inhibitors |
| CN111655695B (zh) | 2017-11-27 | 2025-05-27 | 达特神经科学有限公司 | 作为pde1抑制剂的取代的呋喃并嘧啶化合物 |
| HUE057202T2 (hu) | 2017-12-14 | 2022-04-28 | H Lundbeck As | Kombinációs kezelések 1H-pirazolo[4,3-b]piridinek alkalmazásával |
| AR113926A1 (es) | 2017-12-14 | 2020-07-01 | H Lundbeck As | Derivados de 1h-pirazolo[4,3-b]piridinas |
| TW201927784A (zh) | 2017-12-20 | 2019-07-16 | 丹麥商Ｈ 朗德貝克公司 | 作為pde1抑制劑之大環 |
| WO2019121840A1 (en) | 2017-12-20 | 2019-06-27 | H. Lundbeck A/S | Pyrazolo[3,4-b]pyridines and imidazo[1,5-b]pyridazines as pde1 inhibitors |
| US10766893B2 (en) | 2017-12-20 | 2020-09-08 | H. Lundbeck A/S | 1H-pyrazolo[4,3-b]pyridines as PDE1 inhibitors |
| US11839614B2 (en) | 2018-01-31 | 2023-12-12 | Intra-Cellular Therapies, Inc. | Methods for treating or mitigating cardiotoxicity characterized by inhibition of adenosine A2 signaling and/or adenosine A2 receptor expression |
| US12410175B2 (en) | 2019-09-03 | 2025-09-09 | Intra-Cellular Therapies, Inc. | Compounds |
| WO2021226407A1 (en) | 2020-05-06 | 2021-11-11 | Intra-Cellular Therapies, Inc. | Free base crystals |
| US12364695B2 (en) | 2020-06-02 | 2025-07-22 | Intra-Cellular Therapies, Inc. | Methods of treating inflammatory disease |
| WO2025091011A1 (en) * | 2023-10-26 | 2025-05-01 | Intra-Cellular Therapies, Inc | Organic compounds |
Family Cites Families (72)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| WO1982003626A1 (en) | 1981-04-22 | 1982-10-28 | Gauri Kailash Kumar | New derivatives of pyrazolo(3,4-d)pyrimidine,preparation method thereof and remedy containing them |
| US4469868A (en) | 1982-05-24 | 1984-09-04 | Warner-Lambert Company | Alkylimidazo[1,2-c]pyrazolo[3,4-e]pyrimidines |
| US4666908A (en) * | 1985-04-05 | 1987-05-19 | Warner-Lambert Company | 5-Substituted pyrazolo[4,3-d]pyrimidine-7-ones and methods of use |
| KR920004437B1 (ko) | 1989-09-12 | 1992-06-05 | 삼성전자 주식회사 | 금전등록기의 거래선 관리방법 |
| IL98559A0 (en) * | 1990-06-21 | 1992-07-15 | Schering Corp | Polycyclic guanine derivatives |
| US5202328A (en) | 1991-03-06 | 1993-04-13 | Merck & Co., Inc. | Substituted fused pyrimidinones |
| 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 |
| HUT72640A (en) | 1993-02-26 | 1996-05-28 | Schering Corp | 2-benzyl-polycyclic guanine derivatives, pharmaceutical compositions containing them and process for preparing them |
| GB9304919D0 (en) | 1993-03-10 | 1993-04-28 | Celltech Ltd | Chemical compounds |
| GB9315017D0 (en) | 1993-07-20 | 1993-09-01 | Glaxo Lab Sa | Chemical compounds |
| GB9523675D0 (en) | 1995-11-20 | 1996-01-24 | Celltech Therapeutics Ltd | Chemical compounds |
| US5824683A (en) | 1995-11-28 | 1998-10-20 | Schering Corporation | 2'- 4'-halo- 1,1'-biphenyl!-4-yl!methyl!-5'-methyl-spiro cyclopentane-1,7' (8'H)- 3H! imidazo 2,1-b!purin!-4' (5'H)-ones |
| GB9526245D0 (en) | 1995-12-21 | 1996-02-21 | Celltech Therapeutics Ltd | Chemical compounds |
| GB9622363D0 (en) | 1996-10-28 | 1997-01-08 | Celltech Therapeutics Ltd | Chemical compounds |
| WO1998028281A1 (en) | 1996-12-23 | 1998-07-02 | Celltech Therapeutics Limited | Fused polycyclic 2-aminopyrimidine derivatives, their preparation and their use as protein tyrosine kinase inhibitors |
| 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 |
| US6013621A (en) | 1997-10-17 | 2000-01-11 | The Rockfeller University | Method of treating psychosis and/or hyperactivity |
| GB9722520D0 (en) | 1997-10-24 | 1997-12-24 | Pfizer Ltd | Compounds |
| CA2326324C (en) | 1998-03-31 | 2010-05-11 | Kyowa Hakko Kogyo Co., Ltd. | Nitrogen-containing heterocyclic compound |
| BR9909808A (pt) * | 1998-04-20 | 2000-12-26 | Pfizer | Pirazolopirimidinonas inibidoras de cgmp pde5 para o tratamento da disfunção sexual |
| US6133273A (en) | 1998-05-08 | 2000-10-17 | American Home Products Corporation | Pyrazolopyrimidine-2,4-dione sulfonamides |
| GB9907658D0 (en) | 1999-04-06 | 1999-05-26 | Zeneca Ltd | Chemical compounds |
| US6316444B1 (en) | 1999-06-30 | 2001-11-13 | Merck & Co., Inc. | SRC kinase inhibitor compounds |
| ATE253915T1 (de) | 1999-06-30 | 2003-11-15 | Merck & Co Inc | Src-kinase hemmende verbindungen |
| DE19931206A1 (de) | 1999-07-07 | 2001-01-11 | Stief Christian | Arzneimittel zur Erhöhung des cAMP-Spiegels und deren Verwendung |
| ATE309241T1 (de) | 1999-09-10 | 2005-11-15 | Merck & Co Inc | Tyrosin kinase inhibitoren |
| YU23802A (sh) | 1999-09-30 | 2004-09-03 | Neurogen Corporation | Određeni alkilen diamin-supstituisani pirazolo/1,5-a/-1,5- piramidini i pirazolo/1,5-a/1,3,5-triazini |
| 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 |
| IL149025A0 (en) | 1999-10-11 | 2002-11-10 | Pfizer | 5-(2-substituted-5-heterocyclylsulphonylpyrid-3-yl)-dihydropyrazolo [4, 3-d] pyrimidin-7-ones as phosphodiesterase inhibitors |
| IL139073A0 (en) | 1999-10-21 | 2001-11-25 | Pfizer | Treatment of neuropathy |
| MY125533A (en) | 1999-12-06 | 2006-08-30 | Bristol Myers Squibb Co | Heterocyclic dihydropyrimidine compounds |
| GB0004890D0 (en) | 2000-03-01 | 2000-04-19 | Astrazeneca Uk Ltd | Chemical compounds |
| AU2001255849B8 (en) | 2000-04-19 | 2006-04-27 | Lilly Icos, Llc. | PDE-V inhibitors for treatment of Parkinson's Disease |
| US6693099B2 (en) | 2000-10-17 | 2004-02-17 | The Procter & Gamble Company | Substituted piperazine compounds optionally containing a quinolyl moiety for treating multidrug resistance |
| 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 |
| US6969719B2 (en) | 2001-08-28 | 2005-11-29 | Schering Corporation | Polycyclic guanine phosphodiesterase V inhibitors |
| KR20040066788A (ko) | 2001-08-31 | 2004-07-27 | 더 락커펠러 유니버시티 | 프스포다이에스터레이즈 활성 및 뇌에서프스포다이에스터레이즈 1ｂ 매개되는 신호의 조절 |
| US6943171B2 (en) | 2001-11-09 | 2005-09-13 | Schering Corporation | Polycyclic guanine derivative phosphodiesterase V inhibitors |
| CA2476423A1 (en) | 2002-02-15 | 2003-08-28 | Sympore Gmbh | Conjugates of biologically active compounds, methods for their preparation and use, formulation and pharmaceutical applications thereof |
| US20050153372A1 (en) | 2002-02-21 | 2005-07-14 | Paul Greengard | Compositions and method for regulation of calcium-dependent signaling in brain |
| GB0230045D0 (en) | 2002-12-23 | 2003-01-29 | Glaxo Group Ltd | Compounds |
| WO2004087906A1 (en) | 2003-03-31 | 2004-10-14 | Pfizer Products Inc. | Crystal structure of 3',5'-cyclic nucleotide phosphodiesterase 1b (pde1b) and uses thereof |
| EP1624893A2 (en) | 2003-04-01 | 2006-02-15 | Applied Research Systems ARS Holding N.V. | Inhibitors of phosphodiesterases in infertility |
| CN1878773A (zh) | 2003-09-05 | 2006-12-13 | 神经能质公司 | 作为crf1受体配位体的杂芳基稠合的吡啶,吡嗪及嘧啶 |
| CN103467471A (zh) | 2005-06-06 | 2013-12-25 | 武田药品工业株式会社 | 有机化合物 |
| WO2007025103A2 (en) | 2005-08-23 | 2007-03-01 | Intra-Cellular Therapies, Inc. | Organic compounds for treating reduced dopamine receptor signalling activity |
| US9255099B2 (en) | 2006-06-06 | 2016-02-09 | Intra-Cellular Therapies, Inc. | Pyrazolo[3,4-D]pyrimidine-4,6(5H,7H)-diones as phosphodiesterase 1 inhibitors |
| US20070286890A1 (en) | 2006-06-07 | 2007-12-13 | John Garnett Walt | Eyelash applicator and method |
| US8490581B2 (en) * | 2006-06-15 | 2013-07-23 | Exxonmobil Research And Engineering Company | Advanced fired heater unit for use in refinery and petro-chemical applications |
| EP2081431B1 (en) * | 2006-11-13 | 2013-01-16 | Intra-Cellular Therapies, Inc. | Organic compounds |
| WO2008070095A1 (en) | 2006-12-05 | 2008-06-12 | Intra-Cellular Therapies, Inc. | Novel uses |
| CN104370920A (zh) | 2007-12-06 | 2015-02-25 | 武田药品工业株式会社 | 有机化合物 |
| ES2588238T3 (es) | 2007-12-06 | 2016-10-31 | Intra-Cellular Therapies, Inc. | Derivados de pirazolopirimidin-4,6-diona y su uso como producto farmacéutico |
| JP5710493B2 (ja) | 2008-12-06 | 2015-04-30 | 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 |
| JP5813511B2 (ja) | 2008-12-06 | 2015-11-17 | 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 |
| ES2638912T3 (es) | 2008-12-06 | 2017-10-24 | Intra-Cellular Therapies, Inc. | Compuestos orgánicos |
| EP2358204B1 (en) | 2008-12-06 | 2015-08-05 | Intra-Cellular Therapies, Inc. | 4,5,7,8-tetrahydro-4-oxo-2H-imidazo[1,2-a]pyrrolo[3,4-e]pyrimidine compounds as PDE1 inhibitors. |
| US8633180B2 (en) | 2008-12-06 | 2014-01-21 | Intra-Cellular Therapies, Inc. | Organic compounds |
| US8927556B2 (en) | 2008-12-06 | 2015-01-06 | Intra-Cellular Therapies, Inc. | 1H-pyrrolo[3,4-D]pyrimidin-2(6H)-one compounds |
| JP2012518685A (ja) | 2009-02-25 | 2012-08-16 | イントラ−セルラー・セラピーズ・インコーポレイテッド | 眼障害のためのｐｄｅ１阻害剤 |
| 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 |
| US8858911B2 (en) | 2009-10-08 | 2014-10-14 | Intra-Cellular Therapies, Inc. | Phosphodiesterase 1-targeting tracers and methods |
| TW201206937A (en) | 2010-05-31 | 2012-02-16 | Intra Cellular Therapies Inc | Organic compounds |
| EP2576551A4 (en) | 2010-05-31 | 2014-04-16 | Intra Cellular Therapies Inc | ORGANIC CONNECTIONS |
| EP2575817A4 (en) | 2010-05-31 | 2014-01-08 | Intra Cellular Therapies Inc | ORGANIC CONNECTIONS |
| WO2011153135A1 (en) | 2010-05-31 | 2011-12-08 | Intra-Cellular Therapies, Inc. | Organic compounds |
| US10561656B2 (en) | 2011-06-10 | 2020-02-18 | Intra-Cellular Therapies, Inc. | Organic compounds |
| AR091507A1 (es) | 2012-06-21 | 2015-02-11 | Intra Cellular Therapies Inc | SALES DE (6aR,9aS)-5,6a,7,8,9,9a-HEXAHIDRO-5-METIL-3-(FENILAMINO)-2-((4-(6-FLUOROPIRIDIN-2-IL)FENIL)METIL)-CICLOPENT[4,5]IMIDAZO[1,2-a]PIRAZOLO[4,3-e]PIRIMIDIN-4(2H)-ONA |
-
2007
- 2007-12-05 WO PCT/US2007/024866 patent/WO2008070095A1/en not_active Ceased
- 2007-12-05 US US12/517,945 patent/US9006258B2/en not_active Expired - Fee Related
- 2007-12-05 EP EP07853247A patent/EP2089034A4/en not_active Withdrawn
- 2007-12-05 JP JP2009540267A patent/JP5837278B2/ja not_active Expired - Fee Related
-
2013
- 2013-07-18 JP JP2013149462A patent/JP2013231074A/ja active Pending
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