ES2297864T3 - Pirrolopirimidinas sustituidas y procesos para su preparacion. - Google Patents
Pirrolopirimidinas sustituidas y procesos para su preparacion. Download PDFInfo
- Publication number
- ES2297864T3 ES2297864T3 ES97940108T ES97940108T ES2297864T3 ES 2297864 T3 ES2297864 T3 ES 2297864T3 ES 97940108 T ES97940108 T ES 97940108T ES 97940108 T ES97940108 T ES 97940108T ES 2297864 T3 ES2297864 T3 ES 2297864T3
- Authority
- ES
- Spain
- Prior art keywords
- formula
- pyrrolo
- pyrimidine
- chloroanilino
- radical
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 238000000034 method Methods 0.000 title claims description 50
- 238000002360 preparation method Methods 0.000 title claims description 42
- 230000008569 process Effects 0.000 title claims description 38
- -1 3 -phenylureido Chemical group 0.000 claims abstract description 212
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 67
- 150000003839 salts Chemical class 0.000 claims abstract description 46
- 239000000460 chlorine Substances 0.000 claims abstract description 29
- 239000001257 hydrogen Substances 0.000 claims abstract description 24
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 24
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 15
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 14
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims abstract description 12
- 125000003282 alkyl amino group Chemical group 0.000 claims abstract description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 11
- 125000004299 tetrazol-5-yl group Chemical group [H]N1N=NC(*)=N1 0.000 claims abstract description 10
- 125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 9
- JJTNLWSCFYERCK-UHFFFAOYSA-N 7h-pyrrolo[2,3-d]pyrimidine Chemical class N1=CN=C2NC=CC2=C1 JJTNLWSCFYERCK-UHFFFAOYSA-N 0.000 claims abstract description 6
- 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 claims abstract description 6
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims abstract description 5
- 125000000972 4,5-dimethylthiazol-2-yl group Chemical group [H]C([H])([H])C1=C(N=C(*)S1)C([H])([H])[H] 0.000 claims abstract description 4
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims abstract description 4
- 125000005281 alkyl ureido group Chemical group 0.000 claims abstract description 3
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims abstract description 3
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims abstract 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims abstract 2
- 150000001875 compounds Chemical class 0.000 claims description 204
- 125000001424 substituent group Chemical group 0.000 claims description 54
- 125000006239 protecting group Chemical group 0.000 claims description 51
- 239000002253 acid Substances 0.000 claims description 49
- 125000000524 functional group Chemical group 0.000 claims description 26
- 229910052740 iodine Inorganic materials 0.000 claims description 24
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
- 230000001012 protector Effects 0.000 claims description 19
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 18
- 239000008194 pharmaceutical composition Substances 0.000 claims description 16
- 238000003756 stirring Methods 0.000 claims description 16
- 206010028980 Neoplasm Diseases 0.000 claims description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
- 150000002148 esters Chemical class 0.000 claims description 11
- 150000001412 amines Chemical class 0.000 claims description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 7
- 229910052794 bromium Chemical group 0.000 claims description 7
- 230000006870 function Effects 0.000 claims description 7
- BYYLPECJKOEHBV-UHFFFAOYSA-N 4-(3-chloroanilino)-7h-pyrrolo[2,3-d]pyrimidine-6-carbaldehyde Chemical compound ClC1=CC=CC(NC=2C=3C=C(C=O)NC=3N=CN=2)=C1 BYYLPECJKOEHBV-UHFFFAOYSA-N 0.000 claims description 6
- 241001465754 Metazoa Species 0.000 claims description 6
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 6
- 150000001448 anilines Chemical class 0.000 claims description 6
- 125000004429 atom Chemical group 0.000 claims description 6
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 229910052783 alkali metal Inorganic materials 0.000 claims description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 5
- 125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- BNMRACHWXQYRHO-UHFFFAOYSA-N 4-(3-chloroanilino)-7h-pyrrolo[2,3-d]pyrimidine-6-carbothioamide Chemical compound N1=CN=C2NC(C(=S)N)=CC2=C1NC1=CC=CC(Cl)=C1 BNMRACHWXQYRHO-UHFFFAOYSA-N 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- 150000001340 alkali metals Chemical class 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- OGEBYZFAAZVIHT-UHFFFAOYSA-N N-(3-chlorophenyl)-6-(2H-tetrazol-5-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound ClC1=CC=CC(NC=2C=3C=C(NC=3N=CN=2)C=2NN=NN=2)=C1 OGEBYZFAAZVIHT-UHFFFAOYSA-N 0.000 claims description 3
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 claims description 3
- 125000005036 alkoxyphenyl group Chemical group 0.000 claims description 3
- 150000001351 alkyl iodides Chemical class 0.000 claims description 3
- 239000012024 dehydrating agents Substances 0.000 claims description 3
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 3
- 150000002443 hydroxylamines Chemical class 0.000 claims description 3
- 239000012948 isocyanate Substances 0.000 claims description 3
- CFHGBZLNZZVTAY-UHFFFAOYSA-N lawesson's reagent Chemical compound C1=CC(OC)=CC=C1P1(=S)SP(=S)(C=2C=CC(OC)=CC=2)S1 CFHGBZLNZZVTAY-UHFFFAOYSA-N 0.000 claims description 3
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 3
- YYELWCZQXDCXCI-UHFFFAOYSA-N 1-[3-[4-(3-chloroanilino)-7h-pyrrolo[2,3-d]pyrimidin-6-yl]phenyl]-3-ethylurea Chemical compound CCNC(=O)NC1=CC=CC(C=2NC3=NC=NC(NC=4C=C(Cl)C=CC=4)=C3C=2)=C1 YYELWCZQXDCXCI-UHFFFAOYSA-N 0.000 claims description 2
- UTIXVEICQYJJRY-UHFFFAOYSA-N 1-[3-[4-(3-chloroanilino)-7h-pyrrolo[2,3-d]pyrimidin-6-yl]phenyl]-3-methylthiourea Chemical compound CNC(=S)NC1=CC=CC(C=2NC3=NC=NC(NC=4C=C(Cl)C=CC=4)=C3C=2)=C1 UTIXVEICQYJJRY-UHFFFAOYSA-N 0.000 claims description 2
- TWNRMTYWTBYQQS-UHFFFAOYSA-N 1-[4-[4-(3-chloroanilino)-7h-pyrrolo[2,3-d]pyrimidin-6-yl]phenyl]-3-ethylurea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(NC1=NC=N2)=CC1=C2NC1=CC=CC(Cl)=C1 TWNRMTYWTBYQQS-UHFFFAOYSA-N 0.000 claims description 2
- UCRKSQGCZVGBGX-UHFFFAOYSA-N 1-[4-[4-(3-chloroanilino)-7h-pyrrolo[2,3-d]pyrimidin-6-yl]phenyl]-3-methylthiourea Chemical compound C1=CC(NC(=S)NC)=CC=C1C(NC1=NC=N2)=CC1=C2NC1=CC=CC(Cl)=C1 UCRKSQGCZVGBGX-UHFFFAOYSA-N 0.000 claims description 2
- CGSVJQVCEGIWCF-OAHLLOKOSA-N 1-ethyl-3-[3-[4-[[(1r)-1-phenylethyl]amino]-7h-pyrrolo[2,3-d]pyrimidin-6-yl]phenyl]urea Chemical compound CCNC(=O)NC1=CC=CC(C=2NC3=NC=NC(N[C@H](C)C=4C=CC=CC=4)=C3C=2)=C1 CGSVJQVCEGIWCF-OAHLLOKOSA-N 0.000 claims description 2
- YPCURGZEPMFYLX-OAHLLOKOSA-N 1-ethyl-3-[4-[4-[[(1r)-1-phenylethyl]amino]-7h-pyrrolo[2,3-d]pyrimidin-6-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(NC1=NC=N2)=CC1=C2N[C@H](C)C1=CC=CC=C1 YPCURGZEPMFYLX-OAHLLOKOSA-N 0.000 claims description 2
- VEJBANJNCNEZHG-CQSZACIVSA-N 1-methyl-3-[3-[4-[[(1r)-1-phenylethyl]amino]-7h-pyrrolo[2,3-d]pyrimidin-6-yl]phenyl]thiourea Chemical compound CNC(=S)NC1=CC=CC(C=2NC3=NC=NC(N[C@H](C)C=4C=CC=CC=4)=C3C=2)=C1 VEJBANJNCNEZHG-CQSZACIVSA-N 0.000 claims description 2
- CYMAZKIEYPVYOH-UHFFFAOYSA-N 2-methoxy-4-[4-(3-methylanilino)-7h-pyrrolo[2,3-d]pyrimidin-6-yl]phenol Chemical compound C1=C(O)C(OC)=CC(C=2NC3=NC=NC(NC=4C=C(C)C=CC=4)=C3C=2)=C1 CYMAZKIEYPVYOH-UHFFFAOYSA-N 0.000 claims description 2
- VAKYVBRASQJLDI-UHFFFAOYSA-N 2-methylpropyl n-[4-[4-(3-chloroanilino)-7h-pyrrolo[2,3-d]pyrimidin-6-yl]phenyl]carbamate Chemical compound C1=CC(NC(=O)OCC(C)C)=CC=C1C(NC1=NC=N2)=CC1=C2NC1=CC=CC(Cl)=C1 VAKYVBRASQJLDI-UHFFFAOYSA-N 0.000 claims description 2
- JEWOIKNJTXJTGH-UHFFFAOYSA-N 4-(4-anilino-7h-pyrrolo[2,3-d]pyrimidin-6-yl)-2-methoxyphenol;hydrochloride Chemical compound Cl.C1=C(O)C(OC)=CC(C=2NC3=NC=NC(NC=4C=CC=CC=4)=C3C=2)=C1 JEWOIKNJTXJTGH-UHFFFAOYSA-N 0.000 claims description 2
- WXZNMFZVZMNGIO-UHFFFAOYSA-N 4-[4-(3-chloroanilino)-7h-pyrrolo[2,3-d]pyrimidin-6-yl]-2-methoxyphenol;hydrochloride Chemical compound Cl.C1=C(O)C(OC)=CC(C=2NC3=NC=NC(NC=4C=C(Cl)C=CC=4)=C3C=2)=C1 WXZNMFZVZMNGIO-UHFFFAOYSA-N 0.000 claims description 2
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 2
- VGFSMURRDQKEKB-UHFFFAOYSA-N 6-(3-methoxy-4-phenylmethoxyphenyl)-n-(3-methylphenyl)-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound COC1=CC(C=2NC3=NC=NC(NC=4C=C(C)C=CC=4)=C3C=2)=CC=C1OCC1=CC=CC=C1 VGFSMURRDQKEKB-UHFFFAOYSA-N 0.000 claims description 2
- QOLIVYYSALQXGF-LJQANCHMSA-N 6-[3-(benzylamino)phenyl]-n-[(1r)-1-phenylethyl]-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound N([C@H](C)C=1C=CC=CC=1)C(C=1C=2)=NC=NC=1NC=2C(C=1)=CC=CC=1NCC1=CC=CC=C1 QOLIVYYSALQXGF-LJQANCHMSA-N 0.000 claims description 2
- NIFHYNGZYDVDBU-UHFFFAOYSA-N 6-[4-(benzylamino)phenyl]-n-(3-chlorophenyl)-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound ClC1=CC=CC(NC=2C=3C=C(NC=3N=CN=2)C=2C=CC(NCC=3C=CC=CC=3)=CC=2)=C1 NIFHYNGZYDVDBU-UHFFFAOYSA-N 0.000 claims description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 2
- QOPHSBUZTVLVBJ-UHFFFAOYSA-N N-(3-chlorophenyl)-6-(1-methyltetrazol-5-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound CN1N=NN=C1C(NC1=NC=N2)=CC1=C2NC1=CC=CC(Cl)=C1 QOPHSBUZTVLVBJ-UHFFFAOYSA-N 0.000 claims description 2
- BCZCVGXQOLPACI-UHFFFAOYSA-N N-(3-chlorophenyl)-6-(2-methyltetrazol-5-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound CN1N=NC(C=2NC3=NC=NC(NC=4C=C(Cl)C=CC=4)=C3C=2)=N1 BCZCVGXQOLPACI-UHFFFAOYSA-N 0.000 claims description 2
- GAABGZUDSKAVGH-UHFFFAOYSA-N N-(3-chlorophenyl)-6-(4,5-dimethyl-1,3-thiazol-2-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound S1C(C)=C(C)N=C1C(NC1=NC=N2)=CC1=C2NC1=CC=CC(Cl)=C1 GAABGZUDSKAVGH-UHFFFAOYSA-N 0.000 claims description 2
- ZRSLTYRSYOZHIR-UHFFFAOYSA-N N-(3-chlorophenyl)-6-(4-ethyl-1,3-thiazol-2-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound CCC1=CSC(C=2NC3=NC=NC(NC=4C=C(Cl)C=CC=4)=C3C=2)=N1 ZRSLTYRSYOZHIR-UHFFFAOYSA-N 0.000 claims description 2
- BPEIBTXCKPKWLE-UHFFFAOYSA-N N-(3-chlorophenyl)-6-[4-(4-methoxyphenyl)-1,3-thiazol-2-yl]-7H-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound C1=CC(OC)=CC=C1C1=CSC(C=2NC3=NC=NC(NC=4C=C(Cl)C=CC=4)=C3C=2)=N1 BPEIBTXCKPKWLE-UHFFFAOYSA-N 0.000 claims description 2
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- NUXWAOSDMYECDX-UHFFFAOYSA-N ethyl n-[4-[4-(3-chloroanilino)-7h-pyrrolo[2,3-d]pyrimidin-6-yl]phenyl]carbamate Chemical compound C1=CC(NC(=O)OCC)=CC=C1C(NC1=NC=N2)=CC1=C2NC1=CC=CC(Cl)=C1 NUXWAOSDMYECDX-UHFFFAOYSA-N 0.000 claims description 2
- 150000002513 isocyanates Chemical class 0.000 claims description 2
- 150000002540 isothiocyanates Chemical class 0.000 claims description 2
- ROZJWSLFOMITNR-UHFFFAOYSA-N methyl n-[4-[4-(3-chloroanilino)-7h-pyrrolo[2,3-d]pyrimidin-6-yl]phenyl]carbamate Chemical compound C1=CC(NC(=O)OC)=CC=C1C(NC1=NC=N2)=CC1=C2NC1=CC=CC(Cl)=C1 ROZJWSLFOMITNR-UHFFFAOYSA-N 0.000 claims description 2
- SDSLGPIDULPJQG-MRXNPFEDSA-N n,n-dimethyl-n'-[3-[4-[[(1r)-1-phenylethyl]amino]-7h-pyrrolo[2,3-d]pyrimidin-6-yl]phenyl]methanimidamide Chemical compound N([C@H](C)C=1C=CC=CC=1)C(C=1C=2)=NC=NC=1NC=2C1=CC=CC(N=CN(C)C)=C1 SDSLGPIDULPJQG-MRXNPFEDSA-N 0.000 claims description 2
- PRVIBBCNUUBOSX-UHFFFAOYSA-N n-(3-chlorophenyl)-6-(1,3-thiazol-2-yl)-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound ClC1=CC=CC(NC=2C=3C=C(NC=3N=CN=2)C=2SC=CN=2)=C1 PRVIBBCNUUBOSX-UHFFFAOYSA-N 0.000 claims description 2
- LIPUGMMVKJZMRG-UHFFFAOYSA-N n-(3-chlorophenyl)-6-(3-methoxy-4-phenylmethoxyphenyl)-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound COC1=CC(C=2NC3=NC=NC(NC=4C=C(Cl)C=CC=4)=C3C=2)=CC=C1OCC1=CC=CC=C1 LIPUGMMVKJZMRG-UHFFFAOYSA-N 0.000 claims description 2
- GBCGNNNFIRWGCW-UHFFFAOYSA-N n-(3-chlorophenyl)-6-[4-[(4-methylpiperazin-1-yl)methylideneamino]phenyl]-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound C1CN(C)CCN1C=NC1=CC=C(C=2NC3=NC=NC(NC=4C=C(Cl)C=CC=4)=C3C=2)C=C1 GBCGNNNFIRWGCW-UHFFFAOYSA-N 0.000 claims description 2
- ROLDUDKLNYYONL-UHFFFAOYSA-N n-[3-[4-(3-chloroanilino)-7h-pyrrolo[2,3-d]pyrimidin-6-yl]phenyl]ethanesulfonamide Chemical compound CCS(=O)(=O)NC1=CC=CC(C=2NC3=NC=NC(NC=4C=C(Cl)C=CC=4)=C3C=2)=C1 ROLDUDKLNYYONL-UHFFFAOYSA-N 0.000 claims description 2
- RBEFWIDYHAIBSL-UHFFFAOYSA-N n-[3-[4-(3-chloroanilino)-7h-pyrrolo[2,3-d]pyrimidin-6-yl]phenyl]methanesulfonamide Chemical compound CS(=O)(=O)NC1=CC=CC(C=2NC3=NC=NC(NC=4C=C(Cl)C=CC=4)=C3C=2)=C1 RBEFWIDYHAIBSL-UHFFFAOYSA-N 0.000 claims description 2
- PKNAMUVGIGLHAY-UHFFFAOYSA-N n-[3-[4-(3-chloroanilino)-7h-pyrrolo[2,3-d]pyrimidin-6-yl]phenyl]propane-2-sulfonamide Chemical compound CC(C)S(=O)(=O)NC1=CC=CC(C=2NC3=NC=NC(NC=4C=C(Cl)C=CC=4)=C3C=2)=C1 PKNAMUVGIGLHAY-UHFFFAOYSA-N 0.000 claims description 2
- WVICNPJYDFMIGL-OAHLLOKOSA-N n-[3-[4-[[(1r)-1-phenylethyl]amino]-7h-pyrrolo[2,3-d]pyrimidin-6-yl]phenyl]ethanesulfonamide Chemical compound CCS(=O)(=O)NC1=CC=CC(C=2NC3=NC=NC(N[C@H](C)C=4C=CC=CC=4)=C3C=2)=C1 WVICNPJYDFMIGL-OAHLLOKOSA-N 0.000 claims description 2
- KQWSURRAHQPGAF-CQSZACIVSA-N n-[3-[4-[[(1r)-1-phenylethyl]amino]-7h-pyrrolo[2,3-d]pyrimidin-6-yl]phenyl]methanesulfonamide Chemical compound N([C@H](C)C=1C=CC=CC=1)C(C=1C=2)=NC=NC=1NC=2C1=CC=CC(NS(C)(=O)=O)=C1 KQWSURRAHQPGAF-CQSZACIVSA-N 0.000 claims description 2
- WLMINMLKCZPIDN-UHFFFAOYSA-N n-[4-[4-(3-chloroanilino)-7h-pyrrolo[2,3-d]pyrimidin-6-yl]phenyl]benzenesulfonamide Chemical compound ClC1=CC=CC(NC=2C=3C=C(NC=3N=CN=2)C=2C=CC(NS(=O)(=O)C=3C=CC=CC=3)=CC=2)=C1 WLMINMLKCZPIDN-UHFFFAOYSA-N 0.000 claims description 2
- NDIAGRBKTSAOQM-UHFFFAOYSA-N n-[4-[4-(3-chloroanilino)-7h-pyrrolo[2,3-d]pyrimidin-6-yl]phenyl]propane-2-sulfonamide Chemical compound C1=CC(NS(=O)(=O)C(C)C)=CC=C1C(NC1=NC=N2)=CC1=C2NC1=CC=CC(Cl)=C1 NDIAGRBKTSAOQM-UHFFFAOYSA-N 0.000 claims description 2
- ZXEAZQRLYXDOIU-OAHLLOKOSA-N n-[4-[4-[[(1r)-1-phenylethyl]amino]-7h-pyrrolo[2,3-d]pyrimidin-6-yl]phenyl]ethanesulfonamide Chemical compound C1=CC(NS(=O)(=O)CC)=CC=C1C(NC1=NC=N2)=CC1=C2N[C@H](C)C1=CC=CC=C1 ZXEAZQRLYXDOIU-OAHLLOKOSA-N 0.000 claims description 2
- KJPHJVDDQOMOSH-MRXNPFEDSA-N n-[4-[4-[[(1r)-1-phenylethyl]amino]-7h-pyrrolo[2,3-d]pyrimidin-6-yl]phenyl]propane-2-sulfonamide Chemical compound C1=CC(NS(=O)(=O)C(C)C)=CC=C1C(NC1=NC=N2)=CC1=C2N[C@H](C)C1=CC=CC=C1 KJPHJVDDQOMOSH-MRXNPFEDSA-N 0.000 claims description 2
- MKLSHESXKCZSML-UHFFFAOYSA-N propan-2-yl n-[4-[4-(3-chloroanilino)-7h-pyrrolo[2,3-d]pyrimidin-6-yl]phenyl]carbamate Chemical compound C1=CC(NC(=O)OC(C)C)=CC=C1C(NC1=NC=N2)=CC1=C2NC1=CC=CC(Cl)=C1 MKLSHESXKCZSML-UHFFFAOYSA-N 0.000 claims description 2
- JJJQHTCJNMSSJV-UHFFFAOYSA-N pyrrolo[2,3-d]pyrimidin-4-one Chemical class O=C1N=CN=C2N=CC=C12 JJJQHTCJNMSSJV-UHFFFAOYSA-N 0.000 claims description 2
- 150000004943 pyrrolo[2,3-d]pyrimidines Chemical class 0.000 claims description 2
- 230000001225 therapeutic effect Effects 0.000 claims description 2
- LDUVGYTUBRSPKL-UBKPWBPPSA-N (NE)-N-[[4-(3-chloroanilino)-7H-pyrrolo[2,3-d]pyrimidin-6-yl]methylidene]hydroxylamine Chemical compound N1=CN=C2NC(/C=N/O)=CC2=C1NC1=CC=CC(Cl)=C1 LDUVGYTUBRSPKL-UBKPWBPPSA-N 0.000 claims 1
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- OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical class OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
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- RZWQDAUIUBVCDD-UHFFFAOYSA-M sodium;benzenethiolate Chemical compound [Na+].[S-]C1=CC=CC=C1 RZWQDAUIUBVCDD-UHFFFAOYSA-M 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- GGHPAKFFUZUEKL-UHFFFAOYSA-M sodium;hexadecyl sulfate Chemical compound [Na+].CCCCCCCCCCCCCCCCOS([O-])(=O)=O GGHPAKFFUZUEKL-UHFFFAOYSA-M 0.000 description 1
- NWZBFJYXRGSRGD-UHFFFAOYSA-M sodium;octadecyl sulfate Chemical compound [Na+].CCCCCCCCCCCCCCCCCCOS([O-])(=O)=O NWZBFJYXRGSRGD-UHFFFAOYSA-M 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
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- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 1
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- RSPCKAHMRANGJZ-UHFFFAOYSA-N thiohydroxylamine Chemical compound SN RSPCKAHMRANGJZ-UHFFFAOYSA-N 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
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- 235000019731 tricalcium phosphate Nutrition 0.000 description 1
- 229910000391 tricalcium phosphate Inorganic materials 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
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- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
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- 239000011701 zinc Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- OENHQHLEOONYIE-JLTXGRSLSA-N β-Carotene Chemical compound CC=1CCCC(C)(C)C=1\C=C\C(\C)=C\C=C\C(\C)=C\C=C\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C OENHQHLEOONYIE-JLTXGRSLSA-N 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
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH2071/96 | 1996-08-23 | ||
| CH207196 | 1996-08-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2297864T3 true ES2297864T3 (es) | 2008-05-01 |
Family
ID=4225221
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES97940108T Expired - Lifetime ES2297864T3 (es) | 1996-08-23 | 1997-08-21 | Pirrolopirimidinas sustituidas y procesos para su preparacion. |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US6180636B1 (Direct) |
| EP (1) | EP0938486B1 (Direct) |
| JP (1) | JP4242928B2 (Direct) |
| AT (1) | ATE384062T1 (Direct) |
| AU (1) | AU720429B2 (Direct) |
| CA (1) | CA2262421C (Direct) |
| DE (1) | DE69738468T2 (Direct) |
| DK (1) | DK0938486T3 (Direct) |
| ES (1) | ES2297864T3 (Direct) |
| PT (1) | PT938486E (Direct) |
| WO (1) | WO1998007726A1 (Direct) |
Families Citing this family (146)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6395733B1 (en) * | 1995-06-07 | 2002-05-28 | Pfizer Inc | Heterocyclic ring-fused pyrimidine derivatives |
| AU719434B2 (en) | 1996-02-13 | 2000-05-11 | Astrazeneca Ab | Quinazoline derivatives as VEGF inhibitors |
| ES2169355T3 (es) | 1996-03-05 | 2002-07-01 | Astrazeneca Ab | Derivados de 4-anilinoquinazolina. |
| EP0929553B1 (en) | 1996-10-02 | 2005-03-16 | Novartis AG | Pyrimidine derivatives and processes for the preparation thereof |
| US6187777B1 (en) | 1998-02-06 | 2001-02-13 | Amgen Inc. | Compounds and methods which modulate feeding behavior and related diseases |
| US6686366B1 (en) | 1998-06-02 | 2004-02-03 | Osi Pharmaceuticals, Inc. | Compounds specific to adenosine A3 receptor and uses thereof |
| TR200003513T2 (tr) | 1998-06-02 | 2001-06-21 | Osi Pharmaceuticals, Inc. | Pirolo[2,3d]Pirimidin kompozisyonları ve kullanımları |
| US6878716B1 (en) | 1998-06-02 | 2005-04-12 | Osi Pharmaceuticals, Inc. | Compounds specific to adenosine A1 receptor and uses thereof |
| PA8474101A1 (es) * | 1998-06-19 | 2000-09-29 | Pfizer Prod Inc | Compuestos de pirrolo [2,3-d] pirimidina |
| HRP20000885B1 (hr) * | 1998-06-19 | 2007-03-31 | Pfizer Products Inc. | PIROLO[2,3-d]PIRIMIDINSKI SPOJEVI |
| UA71945C2 (en) * | 1999-01-27 | 2005-01-17 | Pfizer Prod Inc | Substituted bicyclic derivatives being used as anticancer agents |
| EP1676845B1 (en) | 1999-11-05 | 2008-06-11 | AstraZeneca AB | New quinazoline derivatives |
| US6664252B2 (en) | 1999-12-02 | 2003-12-16 | Osi Pharmaceuticals, Inc. | 4-aminopyrrolo[2,3-d]pyrimidine compounds specific to adenosine A2a receptor and uses thereof |
| US7160890B2 (en) | 1999-12-02 | 2007-01-09 | Osi Pharmaceuticals, Inc. | Compounds specific to adenosine A3 receptor and uses thereof |
| US6680322B2 (en) | 1999-12-02 | 2004-01-20 | Osi Pharmaceuticals, Inc. | Compounds specific to adenosine A1 receptors and uses thereof |
| JP4078074B2 (ja) * | 1999-12-10 | 2008-04-23 | ファイザー・プロダクツ・インク | ピロロ［２，３−ｄ］ピリミジン化合物 |
| GB0001930D0 (en) * | 2000-01-27 | 2000-03-22 | Novartis Ag | Organic compounds |
| US7201891B1 (en) * | 2000-05-19 | 2007-04-10 | Otsuka Pharmaceutical Co., Ltd. | Pharmaceutical preparation for the diagnosis of helicobacter pylori infection |
| MXPA02010763A (es) | 2000-06-14 | 2003-03-10 | Warner Lambert Co | Heterociclicos biciclos-6,5 fusionados. |
| CA2412560C (en) | 2000-06-26 | 2008-12-30 | Pfizer Products Inc. | Pyrrolo[2,3-d]pyrimidine compounds as immunosuppressive agents |
| US6673802B2 (en) | 2000-12-01 | 2004-01-06 | Osi Pharmaceuticals, Inc. | Compounds specific to adenosine A3 receptor and uses thereof |
| US6680324B2 (en) | 2000-12-01 | 2004-01-20 | Osi Pharmaceuticals, Inc. | Compounds specific to adenosine A1 receptors and uses thereof |
| GB0031080D0 (en) * | 2000-12-20 | 2001-01-31 | Novartis Ag | Organic compounds |
| US7301023B2 (en) * | 2001-05-31 | 2007-11-27 | Pfizer Inc. | Chiral salt resolution |
| US7323469B2 (en) | 2001-08-07 | 2008-01-29 | Novartis Ag | 7H-pyrrolo[2,3-d]pyrimidine derivatives |
| GB0119249D0 (en) * | 2001-08-07 | 2001-10-03 | Novartis Ag | Organic compounds |
| JP2005529062A (ja) | 2001-11-30 | 2005-09-29 | オーエスアイ・ファーマスーティカルズ・インコーポレーテッド | アデノシンａ１及びａ３受容体に特異的な化合物とその使用 |
| GT200200234A (es) * | 2001-12-06 | 2003-06-27 | Compuestos cristalinos novedosos | |
| CN101973998A (zh) | 2001-12-20 | 2011-02-16 | Osi药物公司 | 吡咯并嘧啶A2b选择性拮抗剂化合物 |
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| JP2000516626A (ja) | 2000-12-12 |
| WO1998007726A1 (en) | 1998-02-26 |
| PT938486E (pt) | 2008-03-27 |
| CA2262421C (en) | 2007-10-02 |
| CA2262421A1 (en) | 1998-02-26 |
| US6180636B1 (en) | 2001-01-30 |
| DK0938486T3 (da) | 2008-07-07 |
| DE69738468T2 (de) | 2009-01-08 |
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