RU2000131690A - NITRATE SALTS OF HYPOTENSIC MEDICINES - Google Patents
NITRATE SALTS OF HYPOTENSIC MEDICINESInfo
- Publication number
- RU2000131690A RU2000131690A RU2000131690/04A RU2000131690A RU2000131690A RU 2000131690 A RU2000131690 A RU 2000131690A RU 2000131690/04 A RU2000131690/04 A RU 2000131690/04A RU 2000131690 A RU2000131690 A RU 2000131690A RU 2000131690 A RU2000131690 A RU 2000131690A
- Authority
- RU
- Russia
- Prior art keywords
- methyl
- dihydro
- residue
- dimethyl
- ethyl
- Prior art date
Links
- 150000002823 nitrates Chemical class 0.000 title claims 16
- 239000003814 drug Substances 0.000 title claims 5
- 125000004432 carbon atoms Chemical group C* 0.000 claims 27
- -1 1H-benzimidazol-2-yl Chemical group 0.000 claims 22
- METKIMKYRPQLGS-GFCCVEGCSA-N (R)-atenolol Chemical compound CC(C)NC[C@@H](O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-GFCCVEGCSA-N 0.000 claims 15
- 229960002274 Atenolol Drugs 0.000 claims 15
- 229910052799 carbon Inorganic materials 0.000 claims 15
- 150000001875 compounds Chemical class 0.000 claims 14
- 229910052739 hydrogen Inorganic materials 0.000 claims 14
- 125000003118 aryl group Chemical group 0.000 claims 9
- AKLNLVOZXMQGSI-UHFFFAOYSA-N Bufetolol Chemical compound CC(C)(C)NCC(O)COC1=CC=CC=C1OCC1OCCC1 AKLNLVOZXMQGSI-UHFFFAOYSA-N 0.000 claims 8
- 229950009385 Bufetolol Drugs 0.000 claims 8
- 125000000623 heterocyclic group Chemical group 0.000 claims 8
- 229910052717 sulfur Inorganic materials 0.000 claims 8
- 239000000203 mixture Substances 0.000 claims 7
- 150000003254 radicals Chemical class 0.000 claims 7
- XSDQTOBWRPYKKA-UHFFFAOYSA-N Amiloride Chemical compound NC(=N)NC(=O)C1=NC(Cl)=C(N)N=C1N XSDQTOBWRPYKKA-UHFFFAOYSA-N 0.000 claims 5
- 239000002083 C09CA01 - Losartan Substances 0.000 claims 5
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N Furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 claims 5
- 229960004773 Losartan Drugs 0.000 claims 5
- KJJZZJSZUJXYEA-UHFFFAOYSA-N Losartan Chemical compound CCCCC1=NC(Cl)=C(CO)N1CC1=CC=C(C=2C(=CC=CC=2)C=2[N]N=NN=2)C=C1 KJJZZJSZUJXYEA-UHFFFAOYSA-N 0.000 claims 5
- IENZQIKPVFGBNW-UHFFFAOYSA-N Prazosin Chemical compound N=1C(N)=C2C=C(OC)C(OC)=CC2=NC=1N(CC1)CCN1C(=O)C1=CC=CO1 IENZQIKPVFGBNW-UHFFFAOYSA-N 0.000 claims 5
- VCKUSRYTPJJLNI-UHFFFAOYSA-N Terazosin Chemical compound N=1C(N)=C2C=C(OC)C(OC)=CC2=NC=1N(CC1)CCN1C(=O)C1CCCO1 VCKUSRYTPJJLNI-UHFFFAOYSA-N 0.000 claims 5
- JBMKAUGHUNFTOL-UHFFFAOYSA-N Aldoclor Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC2=C1NC=NS2(=O)=O JBMKAUGHUNFTOL-UHFFFAOYSA-N 0.000 claims 4
- MAEIEVLCKWDQJH-UHFFFAOYSA-N Bumetanide Chemical compound CCCCNC1=CC(C(O)=O)=CC(S(N)(=O)=O)=C1OC1=CC=CC=C1 MAEIEVLCKWDQJH-UHFFFAOYSA-N 0.000 claims 4
- 229960001222 Carteolol Drugs 0.000 claims 4
- LWAFSWPYPHEXKX-UHFFFAOYSA-N Carteolol Chemical compound N1C(=O)CCC2=C1C=CC=C2OCC(O)CNC(C)(C)C LWAFSWPYPHEXKX-UHFFFAOYSA-N 0.000 claims 4
- JZUFKLXOESDKRF-UHFFFAOYSA-N Dichlothiazide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC2=C1NCNS2(=O)=O JZUFKLXOESDKRF-UHFFFAOYSA-N 0.000 claims 4
- HSUGRBWQSSZJOP-RTWAWAEBSA-N Diltiazem Chemical compound C1=CC(OC)=CC=C1[C@H]1[C@@H](OC(C)=O)C(=O)N(CCN(C)C)C2=CC=CC=C2S1 HSUGRBWQSSZJOP-RTWAWAEBSA-N 0.000 claims 4
- SMANXXCATUTDDT-UHFFFAOYSA-N Flunarizinum Chemical compound C1=CC(F)=CC=C1C(C=1C=CC(F)=CC=1)N1CCN(CC=CC=2C=CC=CC=2)CC1 SMANXXCATUTDDT-UHFFFAOYSA-N 0.000 claims 4
- SGUAFYQXFOLMHL-UHFFFAOYSA-N Labetalol Chemical compound C=1C=C(O)C(C(N)=O)=CC=1C(O)CNC(C)CCC1=CC=CC=C1 SGUAFYQXFOLMHL-UHFFFAOYSA-N 0.000 claims 4
- AQCHWTWZEMGIFD-UHFFFAOYSA-N Metolazone Chemical compound CC1NC2=CC(Cl)=C(S(N)(=O)=O)C=C2C(=O)N1C1=CC=CC=C1C AQCHWTWZEMGIFD-UHFFFAOYSA-N 0.000 claims 4
- HYIMSNHJOBLJNT-UHFFFAOYSA-N Nifedipine Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1C1=CC=CC=C1[N+]([O-])=O HYIMSNHJOBLJNT-UHFFFAOYSA-N 0.000 claims 4
- UIAGMCDKSXEBJQ-UHFFFAOYSA-N Nimodipine Chemical compound COCCOC(=O)C1=C(C)NC(C)=C(C(=O)OC(C)C)C1C1=CC=CC([N+]([O-])=O)=C1 UIAGMCDKSXEBJQ-UHFFFAOYSA-N 0.000 claims 4
- FNYLWPVRPXGIIP-UHFFFAOYSA-N Triurene Chemical compound NC1=NC2=NC(N)=NC(N)=C2N=C1C1=CC=CC=C1 FNYLWPVRPXGIIP-UHFFFAOYSA-N 0.000 claims 4
- SGTNSNPWRIOYBX-UHFFFAOYSA-N Verapamil Chemical compound C1=C(OC)C(OC)=CC=C1CCN(C)CCCC(C#N)(C(C)C)C1=CC=C(OC)C(OC)=C1 SGTNSNPWRIOYBX-UHFFFAOYSA-N 0.000 claims 4
- 125000000468 ketone group Chemical group 0.000 claims 4
- REZGGXNDEMKIQB-UHFFFAOYSA-N 1,4-Dihydro-5-(2-propoxyphenyl)-7H-1,2,3-triazolo[4,5-d]pyrimidin-7-one Chemical compound CCCOC1=CC=CC=C1C1=NC(=O)C2=NNNC2=N1 REZGGXNDEMKIQB-UHFFFAOYSA-N 0.000 claims 3
- TZDPJNSHSWMCPN-UHFFFAOYSA-N 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid Chemical compound OC(=O)C1=C(C)NC(C)=C(C(O)=O)C1C1=CC=CC([N+]([O-])=O)=C1 TZDPJNSHSWMCPN-UHFFFAOYSA-N 0.000 claims 3
- PAZJSJFMUHDSTF-UHFFFAOYSA-N Alprenolol Chemical class CC(C)NCC(O)COC1=CC=CC=C1CC=C PAZJSJFMUHDSTF-UHFFFAOYSA-N 0.000 claims 3
- RZTAMFZIAATZDJ-UHFFFAOYSA-N Felodipine Chemical compound CCOC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1C1=CC=CC(Cl)=C1Cl RZTAMFZIAATZDJ-UHFFFAOYSA-N 0.000 claims 3
- 229960003883 Furosemide Drugs 0.000 claims 3
- ZBBHBTPTTSWHBA-UHFFFAOYSA-N Nicardipine Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OCCN(C)CC=2C=CC=CC=2)C1C1=CC=CC([N+]([O-])=O)=C1 ZBBHBTPTTSWHBA-UHFFFAOYSA-N 0.000 claims 3
- 229960001783 Nicardipine Drugs 0.000 claims 3
- 229960001597 Nifedipine Drugs 0.000 claims 3
- PVHUJELLJLJGLN-UHFFFAOYSA-N Nitrendipine Chemical class CCOC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1C1=CC=CC([N+]([O-])=O)=C1 PVHUJELLJLJGLN-UHFFFAOYSA-N 0.000 claims 3
- 229960001289 Prazosin Drugs 0.000 claims 3
- 229960001693 Terazosin Drugs 0.000 claims 3
- YAPQBXQYLJRXSA-UHFFFAOYSA-N Theobromine Chemical compound CN1C(=O)NC(=O)C2=C1N=CN2C YAPQBXQYLJRXSA-UHFFFAOYSA-N 0.000 claims 3
- NGBFQHCMQULJNZ-UHFFFAOYSA-N Torsemide Chemical compound CC(C)NC(=O)NS(=O)(=O)C1=CN=CC=C1NC1=CC=CC(C)=C1 NGBFQHCMQULJNZ-UHFFFAOYSA-N 0.000 claims 3
- 229960002576 amiloride Drugs 0.000 claims 3
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 3
- 229910052760 oxygen Inorganic materials 0.000 claims 3
- 125000001424 substituent group Chemical group 0.000 claims 3
- HMJIYCCIJYRONP-UHFFFAOYSA-N (+-)-Isradipine Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OC(C)C)C1C1=CC=CC2=NON=C12 HMJIYCCIJYRONP-UHFFFAOYSA-N 0.000 claims 2
- TWBNMYSKRDRHAT-RCWTXCDDSA-N (S)-timolol hemihydrate Chemical compound O.CC(C)(C)NC[C@H](O)COC1=NSN=C1N1CCOCC1.CC(C)(C)NC[C@H](O)COC1=NSN=C1N1CCOCC1 TWBNMYSKRDRHAT-RCWTXCDDSA-N 0.000 claims 2
- HGLLQAPXHCAZBP-UHFFFAOYSA-N 1,3-dimethyl-7-(morpholin-4-ylmethyl)purine-2,6-dione Chemical compound C1=2C(=O)N(C)C(=O)N(C)C=2N=CN1CN1CCOCC1 HGLLQAPXHCAZBP-UHFFFAOYSA-N 0.000 claims 2
- BQXQGZPYHWWCEB-UHFFFAOYSA-N 1-(9H-carbazol-4-yloxy)-3-(propan-2-ylamino)propan-2-ol Chemical compound N1C2=CC=CC=C2C2=C1C=CC=C2OCC(O)CNC(C)C BQXQGZPYHWWCEB-UHFFFAOYSA-N 0.000 claims 2
- QQUGAJMOSWOMFG-UHFFFAOYSA-N 2-(2-aminoethoxymethyl)-4-(2-chlorophenyl)-6-methyl-1,4-dihydropyridine-3,5-dicarboxylic acid Chemical compound OC(=O)C1=C(COCCN)NC(C)=C(C(O)=O)C1C1=CC=CC=C1Cl QQUGAJMOSWOMFG-UHFFFAOYSA-N 0.000 claims 2
- YRZQHIVOIFJEEE-UHFFFAOYSA-N 2-N-(4-chlorophenyl)-1,3,5-triazine-2,4-diamine Chemical compound NC1=NC=NC(NC=2C=CC(Cl)=CC=2)=N1 YRZQHIVOIFJEEE-UHFFFAOYSA-N 0.000 claims 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 2
- FXNYSZHYMGWWEZ-UHFFFAOYSA-N 6-amino-3-methyl-1-(2-methylprop-2-enyl)pyrimidine-2,4-dione Chemical compound CC(=C)CN1C(N)=CC(=O)N(C)C1=O FXNYSZHYMGWWEZ-UHFFFAOYSA-N 0.000 claims 2
- VGLGVJVUHYTIIU-UHFFFAOYSA-N 6-chloro-1,1-dioxo-3-(prop-2-enylsulfanylmethyl)-3,4-dihydro-2H-1$l^{6},2,4-benzothiadiazine-7-sulfonamide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC2=C1NC(CSCC=C)NS2(=O)=O VGLGVJVUHYTIIU-UHFFFAOYSA-N 0.000 claims 2
- VXLCNTLWWUDBSO-UHFFFAOYSA-N 6-chloro-3-ethyl-1,1-dioxo-3,4-dihydro-2H-1$l^{6},2,4-benzothiadiazine-7-sulfonamide Chemical compound ClC1=C(S(N)(=O)=O)C=C2S(=O)(=O)NC(CC)NC2=C1 VXLCNTLWWUDBSO-UHFFFAOYSA-N 0.000 claims 2
- WRYZEGZNBYOMLE-UHFFFAOYSA-N 6-hydrazinylpyridazine-3-carboxamide Chemical compound NNC1=CC=C(C(N)=O)N=N1 WRYZEGZNBYOMLE-UHFFFAOYSA-N 0.000 claims 2
- HTIQEAQVCYTUBX-UHFFFAOYSA-N Amlodipine Chemical compound CCOC(=O)C1=C(COCCN)NC(C)=C(C(=O)OC)C1C1=CC=CC=C1Cl HTIQEAQVCYTUBX-UHFFFAOYSA-N 0.000 claims 2
- NDTSRXAMMQDVSW-UHFFFAOYSA-N Benzthiazide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(S(N2)(=O)=O)=C1N=C2CSCC1=CC=CC=C1 NDTSRXAMMQDVSW-UHFFFAOYSA-N 0.000 claims 2
- BWSSMIJUDVUASQ-UHFFFAOYSA-N Benzylhydrochlorothiazide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(S(N2)(=O)=O)=C1NC2CC1=CC=CC=C1 BWSSMIJUDVUASQ-UHFFFAOYSA-N 0.000 claims 2
- 229960003588 Bevantolol Drugs 0.000 claims 2
- HXLAFSUPPDYFEO-UHFFFAOYSA-N Bevantolol Chemical compound C1=C(OC)C(OC)=CC=C1CCNCC(O)COC1=CC=CC(C)=C1 HXLAFSUPPDYFEO-UHFFFAOYSA-N 0.000 claims 2
- HQIRNZOQPUAHHV-UHFFFAOYSA-N Bupranolol Chemical compound CC1=CC=C(Cl)C(OCC(O)CNC(C)(C)C)=C1 HQIRNZOQPUAHHV-UHFFFAOYSA-N 0.000 claims 2
- 229960002155 Chlorothiazide Drugs 0.000 claims 2
- JIVPVXMEBJLZRO-UHFFFAOYSA-N Chlortalidone Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C2(O)C3=CC=CC=C3C(=O)N2)=C1 JIVPVXMEBJLZRO-UHFFFAOYSA-N 0.000 claims 2
- DERZBLKQOCDDDZ-JLHYYAGUSA-N Cinnarizine Chemical compound C1CN(C(C=2C=CC=CC=2)C=2C=CC=CC=2)CCN1C\C=C\C1=CC=CC=C1 DERZBLKQOCDDDZ-JLHYYAGUSA-N 0.000 claims 2
- RINBGYCKMGDWPY-UHFFFAOYSA-N Epitizide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC2=C1NC(CSCC(F)(F)F)NS2(=O)=O RINBGYCKMGDWPY-UHFFFAOYSA-N 0.000 claims 2
- ZCKKHYXUQFTBIK-KTKRTIGZSA-N Etozoline Chemical compound O=C1N(C)C(=C/C(=O)OCC)/SC1N1CCCCC1 ZCKKHYXUQFTBIK-KTKRTIGZSA-N 0.000 claims 2
- 229960003580 Felodipine Drugs 0.000 claims 2
- NMKSAYKQLCHXDK-UHFFFAOYSA-N Fendiline Chemical compound C=1C=CC=CC=1C(C)NCCC(C=1C=CC=CC=1)C1=CC=CC=C1 NMKSAYKQLCHXDK-UHFFFAOYSA-N 0.000 claims 2
- DMDGGSIALPNSEE-UHFFFAOYSA-N Hydroflumethiazide Chemical compound C1=C(C(F)(F)F)C(S(=O)(=O)N)=CC2=C1NCNS2(=O)=O DMDGGSIALPNSEE-UHFFFAOYSA-N 0.000 claims 2
- 229960004569 Indapamide Drugs 0.000 claims 2
- NDDAHWYSQHTHNT-UHFFFAOYSA-N Indapamide Chemical compound CC1CC2=CC=CC=C2N1NC(=O)C1=CC=C(Cl)C(S(N)(=O)=O)=C1 NDDAHWYSQHTHNT-UHFFFAOYSA-N 0.000 claims 2
- ZDXUKAKRHYTAKV-UHFFFAOYSA-N Lercanidipine Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OC(C)(C)CN(C)CCC(C=2C=CC=CC=2)C=2C=CC=CC=2)C1C1=CC=CC([N+]([O-])=O)=C1 ZDXUKAKRHYTAKV-UHFFFAOYSA-N 0.000 claims 2
- 229960004294 Lercanidipine Drugs 0.000 claims 2
- ZBIAKUMOEKILTF-UHFFFAOYSA-N Lidoflazine Chemical compound CC1=CC=CC(C)=C1NC(=O)CN1CCN(CCCC(C=2C=CC(F)=CC=2)C=2C=CC(F)=CC=2)CC1 ZBIAKUMOEKILTF-UHFFFAOYSA-N 0.000 claims 2
- JQSAYKKFZOSZGJ-UHFFFAOYSA-N Lomerizine Chemical compound COC1=C(OC)C(OC)=CC=C1CN1CCN(C(C=2C=CC(F)=CC=2)C=2C=CC(F)=CC=2)CC1 JQSAYKKFZOSZGJ-UHFFFAOYSA-N 0.000 claims 2
- NXWGWUVGUSFQJC-UHFFFAOYSA-N Mepindolol Chemical compound CC(C)NCC(O)COC1=CC=CC2=C1C=C(C)N2 NXWGWUVGUSFQJC-UHFFFAOYSA-N 0.000 claims 2
- RLWRMIYXDPXIEX-UHFFFAOYSA-N Muzolimine Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(C)N1N=C(N)CC1=O RLWRMIYXDPXIEX-UHFFFAOYSA-N 0.000 claims 2
- 229960000715 Nimodipine Drugs 0.000 claims 2
- OMCPLEZZPVJJIS-UHFFFAOYSA-N Nipradilol Chemical compound C1C(O[N+]([O-])=O)COC2=C1C=CC=C2OCC(O)CNC(C)C OMCPLEZZPVJJIS-UHFFFAOYSA-N 0.000 claims 2
- 229950000754 Nipradilol Drugs 0.000 claims 2
- 229960005425 Nitrendipine Drugs 0.000 claims 2
- IFFPICMESYHZPQ-UHFFFAOYSA-N Prenylamine Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)CCNC(C)CC1=CC=CC=C1 IFFPICMESYHZPQ-UHFFFAOYSA-N 0.000 claims 2
- HRSANNODOVBCST-UHFFFAOYSA-N Pronethalol Chemical group C1=CC=CC2=CC(C(O)CNC(C)C)=CC=C21 HRSANNODOVBCST-UHFFFAOYSA-N 0.000 claims 2
- AQHHHDLHHXJYJD-UHFFFAOYSA-N Proprasylyt Chemical compound C1=CC=C2C(OCC(O)CNC(C)C)=CC=CC2=C1 AQHHHDLHHXJYJD-UHFFFAOYSA-N 0.000 claims 2
- AGMMTXLNIQSRCG-UHFFFAOYSA-N Quinethazone Chemical compound NS(=O)(=O)C1=C(Cl)C=C2NC(CC)NC(=O)C2=C1 AGMMTXLNIQSRCG-UHFFFAOYSA-N 0.000 claims 2
- BNRNXUUZRGQAQC-UHFFFAOYSA-N Sildenafil Chemical compound CCCC1=NN(C)C(C(N2)=O)=C1N=C2C(C(=CC=1)OCC)=CC=1S(=O)(=O)N1CCN(C)CC1 BNRNXUUZRGQAQC-UHFFFAOYSA-N 0.000 claims 2
- NXQMNKUGGYNLBY-UHFFFAOYSA-N Toliprolol Chemical compound CC(C)NCC(O)COC1=CC=CC(C)=C1 NXQMNKUGGYNLBY-UHFFFAOYSA-N 0.000 claims 2
- 229950000245 Toliprolol Drugs 0.000 claims 2
- 229960001288 Triamterene Drugs 0.000 claims 2
- LMJSLTNSBFUCMU-UHFFFAOYSA-N Trichlormethiazide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC2=C1NC(C(Cl)Cl)NS2(=O)=O LMJSLTNSBFUCMU-UHFFFAOYSA-N 0.000 claims 2
- RKUQLAPSGZJLGP-UHFFFAOYSA-N Xibenolol Chemical compound CC1=CC=CC(OCC(O)CNC(C)(C)C)=C1C RKUQLAPSGZJLGP-UHFFFAOYSA-N 0.000 claims 2
- GYKFWCDBQAFCLJ-RTWAWAEBSA-N [(2S,3S)-8-chloro-5-[2-(dimethylamino)ethyl]-2-(4-methoxyphenyl)-4-oxo-2,3-dihydro-1,5-benzothiazepin-3-yl] acetate Chemical compound C1=CC(OC)=CC=C1[C@H]1[C@@H](OC(C)=O)C(=O)N(CCN(C)C)C2=CC=C(Cl)C=C2S1 GYKFWCDBQAFCLJ-RTWAWAEBSA-N 0.000 claims 2
- 229960000528 amlodipine Drugs 0.000 claims 2
- HDWIHXWEUNVBIY-UHFFFAOYSA-N bendroflumethiazidum Chemical compound C1=C(C(F)(F)F)C(S(=O)(=O)N)=CC(S(N2)(=O)=O)=C1NC2CC1=CC=CC=C1 HDWIHXWEUNVBIY-UHFFFAOYSA-N 0.000 claims 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- 229960004064 bumetanide Drugs 0.000 claims 2
- 229960000330 bupranolol Drugs 0.000 claims 2
- 229960004634 carazolol Drugs 0.000 claims 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 2
- 229960004166 diltiazem Drugs 0.000 claims 2
- 229940079593 drugs Drugs 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 229960002003 hydrochlorothiazide Drugs 0.000 claims 2
- 125000002346 iodo group Chemical group I* 0.000 claims 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
- 229960004427 isradipine Drugs 0.000 claims 2
- 229960001632 labetalol Drugs 0.000 claims 2
- 229960003134 mepindolol Drugs 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 229960002817 metolazone Drugs 0.000 claims 2
- 125000001624 naphthyl group Chemical group 0.000 claims 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N oxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 2
- 239000001301 oxygen Substances 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 229960003310 sildenafil Drugs 0.000 claims 2
- 239000011780 sodium chloride Substances 0.000 claims 2
- 229960004605 timolol Drugs 0.000 claims 2
- 229960005461 torasemide Drugs 0.000 claims 2
- 229960002070 torsemide Drugs 0.000 claims 2
- 229960001722 verapamil Drugs 0.000 claims 2
- 229950001124 xibenolol Drugs 0.000 claims 2
- 229950005371 zaprinast Drugs 0.000 claims 2
- KOHIRBRYDXPAMZ-YHBROIRLSA-N (1R,1'R)-2,2'-iminobis{1-[(2R,2'S)-6-fluoro-3,4-dihydro-2H-chromen-2-yl]ethanol} Chemical compound C1CC2=CC(F)=CC=C2O[C@H]1[C@H](O)CNC[C@@H](O)[C@H]1OC2=CC=C(F)C=C2CC1 KOHIRBRYDXPAMZ-YHBROIRLSA-N 0.000 claims 1
- PWWYQZOIPIJRJV-UHFFFAOYSA-N 1,2-dihydrophthalazine Chemical compound C1=CC=C2CNN=CC2=C1 PWWYQZOIPIJRJV-UHFFFAOYSA-N 0.000 claims 1
- MXRGZXBFSKSZPH-UHFFFAOYSA-N 1-(2-hydroxypropyl)-3,7-dimethylpurine-2,6-dione Chemical compound O=C1N(CC(O)C)C(=O)N(C)C2=C1N(C)C=N2 MXRGZXBFSKSZPH-UHFFFAOYSA-N 0.000 claims 1
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- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
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- AQNDDEOPVVGCPG-UHFFFAOYSA-N esmolol Chemical group COC(=O)CCC1=CC=C(OCC(O)CNC(C)C)C=C1 AQNDDEOPVVGCPG-UHFFFAOYSA-N 0.000 claims 1
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- VKQFCGNPDRICFG-UHFFFAOYSA-N methyl 2-methylpropyl 2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OCC(C)C)C1C1=CC=CC=C1[N+]([O-])=O VKQFCGNPDRICFG-UHFFFAOYSA-N 0.000 claims 1
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- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 1
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims 1
- RONWGALEIBILOG-VMJVVOMYSA-N quinine sulfate Chemical compound [H+].[H+].[O-]S([O-])(=O)=O.C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21.C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 RONWGALEIBILOG-VMJVVOMYSA-N 0.000 claims 1
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- 0 C[C@](*)(C*)C(C)=NC1NC1 Chemical compound C[C@](*)(C*)C(C)=NC1NC1 0.000 description 7
Claims (15)
Класс (Alb):
RA1 = -CH2OH,
R1= H, Cl;
RA1 II = (СH2)3-СН3, -O-СН2-СН3;
RA1 III = Н, свободная валентность;
RA1 IV = свободная валентность;
или RA1 = -О и RA1 III = свободная валентность образуют с атомом углерода в 5 положении кето группу,
или RA1 IV, RA1 III, RA1 I и атомы углерода в 4 и 5 положении гетероциклического кольца формулы (A1b) образуют ароматическое кольцо, содержащее СООН группу (IХс),
или RA1 I, RA1 IV и атом углерода в 4 положении гетероциклического кольца формулы (Alb) образуют следующее насыщенное кольцо, имеющее пять атомов углерода:
когда RA1 III = свободная валентность и RA1 IV = свободная валентность является двойной связью между атомами углерода в 4 и 5 положениях гетероциклического кольца формулы (Alb),
Класс (Alc):
Предшественник класса (Alc) известен как вальзартан;
Класс (А2):
1(2Н)-фталазинонгидразон (гидралазин); 6-(1-пиперидинил)-2,4-пиримидиндиамин-3-оксид (миноксидил); 1-[[3-(4,7-дигидро-1-метил-7-оксо-3-пропил-1Н-пиразол[4,3-d] пиримидин-5-ил)-4-этоксифенил] сульфонил] -4-метилпиперазин (силденафил), 2-(2-пропилоксифенил)-8-азапурин-6-он (запринаст);
Класс (А3):
RB1 VI = H
RB1 VII = H
RB1 I и RB1 II равны или отличны друг от друга и означают H, СН3,
RB1 III = H, CH3,
-CH2-CH2-YB1 (XIe),
в формуле (XId)t = 0,1;
в формуле (Xle) YB1 может иметь следующие значения:
в формуле (XIf)Z = H, -ОСН3;
в формуле (A3):
XB1 = -О-, -S-;
n и m равны или отличны друг от друга и составляют 0, 1;
-CH2-CH(OH)-CH2-NH-CH(CH3)2 (XIr),
в формуле (ХIр):
S1= Н, CN, ОСН3, СН3, -СН2-СН3, -О-CH2-СОNН-СН3, -СОСН3, -СО-(СН2)2-СН3, -O-СН2-СН= СН2, -СН2-СН= СН2, циклопентил или
S2= Н, СН3, Сl, -SOСH3, -CONH2;
S3 = H, F, Cl, ОН, NO2, -CH2-CO-NH2, - (СН2)2-ОСН3, -NH-СОСН3,
-СН2-O-СН2-СН2-O-СН(СН3)2, -СН2-СН2-СООСН3, -NH-CO-N(С2Н5)2,
-NН-СО-(СН2)2-СН3, -NH-SO2-СН3, -NH-CO-NH-[циклогексил] , -СН2-СН2-O-СН2-[циклопропил] ; S4 = H, Cl, -СН2-СН2- или
S1, S2 и атомами углерода во 2 и 3 положениях ароматического кольца из шести атомов углерода вышеупомянутого радикала (XIp) образуют следующее кольцо:
где (*) атом, расположенный рядом с ароматическим кольцом формулы XIpVII
В = -CH2-, -NH-, -СН-СН-, (*)-CO-CH2-;
А = -О-, (*)-СН2-СH(ОН)-, (*)-O-CH2-, (*)-S-CH2-, -CH2-СН2, -CH2-,
W1 = H, свободная валентность;
W2 = свободная валентность, H, OH, -CH3, -ONO2, -O;
или А является третичным углеродным атомом и одновременно W1 означает свободную валентность, чтобы образовать двойную связь -СН= СН- между А и атомом углерода в 1' положении;
или W1, W2 атом углерода в 1' положении и А образуют ароматическое кольцо, имеющее шесть атомов углерода, согласно следующей формуле:
когда W2 = -О и W1 = свободная валентность с атомом углерода в 1' положении радикала (XIpVII) образуется кетонная группа;
или когда в формуле (ХIр) S4 = -СН2-СН2-, и в формуле (A3) XB1 является кислород, m = n = 1 и RB1 VII = свободная валентность, образуется следующее кольцо с атомами углерода в 1 и 6 положении ароматического кольца радикала (ХIр):
или когда в формуле (A3) n = m = 1, оба RB1 VII и RB1 VI = свободная валентность, S4 и атомы углерода в 1 и 6 положении ароматического кольца формулы (XIp), S1 является -СН2-СН3, вместе с атомом углерода -| C| n- и XB1 = кислород формулы (A3) образуют следующее кольцо:
и, кроме того, следующие соединения:
2-гидрокси-5-[1-гидрокси-2-[(1-метил-3-фенилпропил)амино] этил] бензамид(лабеталол), 1-(4-амино-6,7-диметокси-2-хиназолинил)-4-[(тетрагидро-2-фуранил)карбонил] пиперазин (теразосин), 1-(4-амино-6,7-диметокси-2-хиназолинил)-4-(2-фуранилкарбонил)пиперазин(празосин);
исключая в формуле (A3) соединения, полученные, когда заместители указанной формулы имеют следующие значения:
RB1 I = RB1 II = RB1 III = CH3; RB1 V = H; n = 1; m = 1
RB1 VI = RB1 VII = H, XB1 = 0; RB1 IV = радикал XIp, где
S1 = S2 = S4 = H, S3= -NH-CO-NH-[циклогексил] (талинол);
RB1 I = RB1 II = CH3; n = 1; RB1 III = RB1 V = RB1 VII = RB1 VII = H;
XB1 VI = 0; RB1 IV является ароматическим кольцом (XIp)
с S2 = S3 = S4 = H, S1 = -СН2-СН-СН 2(альпренолол)
Класс (А4):
(А4а) β-[(2-метилпропокси)метил] -N-фенил-N-(фенилметил)-1-пирролидинэтанамин(бепридил), (2S-цис)-3-(ацетилокси)-8-хлор-5-[2-(диметиламино)этил] -2,3-дигидро-2-(4-метоксифенил)-1,5-бензотиазепин-4(5Н)-он(клентиазем), (2S-цис)-3-(ацетилокси)-5-[2-(диметиламино)этил] -2,3-дигидро-2-(4-метоксифенил)-1,5-бензотиазепин-4(5Н)-он (дилтиазем), γ-фенил-N-(1-фенилэтил) бензол-пропанамин (фендилин), α-[3-[[2-(3,4-диметоксифенил)этил] метиламина] пропил] -3,4,5-триметокси-α-(1-метилэтил)-бензолацетонитрил (галлопамил), (1S-цис)метоксиуксусная кислота-2-[2[[3-(1Н-бензимидазол-2-ил)пропил] метиламино] этил] -6-фтор-1,2,3,4-тетрагидро-1-(1-метилэтил)-2-нафталиновый эфир (мибефрадил), N-(1-метил-2-фенилэтил)-γ-фенилбензолпропанамин (прениламин), (R)-2-[2-[3-[[2-(1,3-бензодиоксол-5-илокси)этил] метиламино] пропокси] -5-метоксифенил] -4-метил-2Н-1,4-бензотиазин-3(4Н)-он (семотиадил), N-(1,1-диметилэтил) -α-метил-γ-фенилбензолпропан-амин (теродилин), α-[3-[[2-(3,4-диметоксифенил)-этил] метил-амино] пропил] -3,4-диметокси-α-(1-метилэтил)-бензолацетонитрил (верапамил);
(А4b) 3-этил-5-метиловый эфир 2-[(2-аминоэтокси)метил] -4-(2-хлорфенил)-1,4-дигидро-6-метил-3,5-пиридиндикарбоновой кислоты (амлодипин), метил-2-оксопропиловый эфир 1,4-дигидро-2,6-диметил-4-(2-нитрофенил)-3,5-пиридиндикарбоновой кислоты (аранидипин), метил-1-(фенилметил)-3-пирролидиниловый эфир [S-(R*, R*)] -1,4-дигидро-2,6-диметил-4-(3-нитрофенил)-3,5-пиридиндикарбоновой кислоты (барнидипин), метил-1-(фенилметил)-3-пиперидиниловый эфир (R*, R*)-±-1,4-дигидро-2,6-диметил-4-(3-нитрофенил)-3,5-пиридиндикарбоновой кислоты (бенидипин), 2-метоксиэтил-3-фенил-2-пропениловый эфир (Е)-±-1,4-дигидро-2,6-диметил-4-(3-нитрофенил)-3,5-пиридиндикарбоновой кислоты (цильнидипин), 2[фенил(фенилметил)амино] этиловый эфир 5-(5,5-диметил-1,3,2-диоксафосфоринан-2-ил)-1,4-дигидро-2,6-диметил-4-(3-нитрофенил)-3-пиридин карбоновой кислоты Р-оксид (эфонидипин), 2[[4-фторфенил)метил] метиламино] этил-1-метилэтиловый эфир ±-4-(1, 3-бензодиоксол-4-ил)-1,4-дигидро-2,6-диметил-3,5-пиридиндикарбоновой кислоты (эльгодипин), этилметиловый эфир 4-(2,3-дихлорфенил)-1,4-дигидро-2,6-диметил-3,5-пиридиндикарбоновой кислоты (фелодипин), 5-метил-3-(1-метил)-этиловый эфир 4-(4-бензофуразанил)-1,4-дигидро-2,6-диметил-3,5-пиридиндикарбоновой кислоты (исрадипин), диэтиловый эфир (Е)-4-[2-[3-(1,1-диметилэтокси)-3-оксо-1-пропенил] фенил] -1,4-дигидро-2,6-диметил-3,5-пиридиндикарбоновой кислоты (лацидипин), 2-[(3,3-дифенилпропил)метиламине] -1,1-диметилэтилметиловый эфир 1,4-дигидро-2,6-диметил-4-(3-нитрофенил)-3,5-пиридиндикарбоновой кислоты (лерканидипин), 2-[4-(дифенилметил)-1-пиперазинил] -этилметиловый эфир 1,4-дигидро-2,6-диметил-4-(3-нитрофенил)-3,5-пиридиндикарбоновой кислоты (манидипин), метил-2-[метил(фенилметил)-амино] этиловый эфир 1,4-дигидро-2,6-диметил-4-(3-нитрофенил)-3,5-пиридиндикарбоновой кислоты (никардипин), диметиловый эфир 1, 4-дигидро-2,6-диметил-4-(2-нитрофенил)-3,5-пиридиндикарбоновой кислоты (нифедипин), 3-метил-5-(1-метилэтил) эфир 2-циано-1,4-дигидро-6-метил-4-(3-нитрофенил)-3,5-пиридиндикарбоновой кислоты (нильвадипин), 2-метоксиэтил-1-метилэтиловый эфир 1,4-дигидро-2,6-диметил-4-(3-нитрофенил)-3,5-пиридиндикарбоновой кислоты (нимодипин), метил-2-метилпропиловый эфир 1,4-дигидро-2,6-диметил-4-(2-нитрофенил)-3,5-пиридиндикарбоновой кислоты (низольдипин), этилметиловый эфир 1,4-дигидро-2,6-диметил-4-(3-нитрофенил)-3,5-пиридиндикарбоновой кислоты (нитрендипин);
(А4с) 1-(дифенилметил)-4-(3-фенил-2-пропенил)пиперазин (циннаризин), (Е)-1-[бис(4-фторфенил)метил] -4-(3-фенил-2-пропенил) пиперазин (флунаризин), 4-[4,4-бис(4-фторфенил)бутил] -N-(2,6-диметилфенил)-1-пиперазинацетамид (лидофлазин), 1-[бис(4-фторфенил)метил] -4-[(2,3,4-триметоксифенил)метил] пиперазин (ломеризин);
(A4d) N, N-диметил-3-[[1-(фенилметил)-циклогептил] окси] -1-пропанамин (бенциклан), 1-[2-[2-(диэтиламино)этокси] фенил] -3-фенил-1-пропанон (этафенон), 3,4-диметокси-N-метил-N-[3-[4-[[2-(1-метилэтил)-1-индолизинил] сульфонил] фенокси] -пропил] бензолэтанамин (фантофарон);
Класс (А7):
(А7а) 6-хлор-3,4-дигидро-3-[(2-пропенилтио)метил] -2Н-1,2,4-бензотиадиазин-7-сульфонамид 1,1-диоксид(альтиазид), 3,4-дигидро-3- (фенилметил)-6-(трифторметил)-2Н-1,2,4-бензотиадиазин-7-сульфонамид 1,1-диоксид (бендрофлуметиазид), (6-хлор-3-[[(фенилметил)тио] метил] -2Н-1,2,4-бензотиадиазин-7-сульфонамид-1,1-диоксид (бензтиазид), 6-хлор-3,4-дигидро-3-(фенилметил)-2Н-1,2,4-бензотиадиазин-7-сульфонамид 1,1-диоксид (бензилгид-рохлортиазид), 6-хлор-3,4-дигидро-3-(2-метилропил)-2Н-1,2,4-бензотиадиазин-7-сульфонамид 1,1-диоксид (бутиазид), 6-хлор-2Н-1,2,4-бензотиадиазин-7-сульфонамид 1,1-диоксид (хлортиазид), 2-хлор-5-(2,3-дигидро-1-гидрокси-3-оксо-1Н-изоиндол-1-ил)бензобесульфонамид (хлорталидон), 6-хлор-3-(циклопентилметил)-3,4-дигидро-2Н-1,2,4-бензотиадиазин-7-сульфонамид 1,1-диоксид (циклопентиазид), 3-бицикло[2,2,1] -гепт-5-ен-2-ил-6-хлор-3,4-дигидро-2Н-1,2,4-бензотиадиазин-7-сульфонамид 1,1-диоксид (циклотиазид), 6-хлор-3,4-дигидро-3-[[(2,2,2-трифторэтил)тио] метил] -2Н-1,2,4-бензотиадиазин-7-сульфонамид 1,1-диоксид (эпитиазид), 6-хлор-3-этил-3,4-дигидро-2Н-1,2,4-бензотиадиазин-7-сульфонамид 1,1-диоксид (этиазид), 7-хлор-1,2,3,4-тетрагидро-4-оксо-2-фенил-6-хиназолинсульфонамид (фенхизон), 3-(аминосульфонил)-4-хлор-N-(2,3-дигидро-2-метил-1Н-индол-1-ил)бензамид (индапамид), 6-хлор-3,4-дигидро-2Н-1,2,4-бензотиадиазин-7-сульфонамид 1,1-диоксид (гидрохлортиазид), 3,4-дигидро-6-(трифторметил)-2Н-1,2,4-бензотиадиазин-7-сульфонамид 1,1-диоксид (гидрофлуметиазид), 6-хлор-3-(хлорметил)-3,4-дигидро-2-метил-2Н-1,2,4-бензотиадиазин-7-сульфонамид 1,1-диоксид (метиклотиазид), 3,4-дигидро-6-метил-2Н-1-бензотиопиран-7-сульфонамид 1,1-диоксид (метикран), 7-хлор-1,2,3,4-тетрагидро-2-метил-3-(2-метилфенил)-4-оксо-6-хиназолинсульфонамид (метолазон), 6-хлор-3-[(4-фторфенил)-метил] -3,4-дигидро-2Н-1,2,4-бензотиадиазин-7-сульфонамид 1,1-диоксид (парафлутизид), 6-хлор-3,4-дигидро-2-метил-3-[[(2,2,2-трифторэтил) тио] метил] -2Н-1,2,4-бензотиадиазин-7-сульфонамид 1,1-диоксид (политиазид), 7-хлор-2-этил-1,2,3,4-тетрагидро-4-оксо-6-хиназолинсульфонамид (хинетазон), 6-хлор-3,4-дигидро-3-трихлорметил-2Н-1,2,4-бензотиадиазин-7-сульфонамид 1,1-диоксид (теклотиазид), 6-хлор-3-(дихлорметил)-3,4-дигидро-2Н-1,2,4-бензотиадиазин-7-сульфонамид 1,1-диоксид (трихлорметиазид);
(А7b) 3,7-дигидро-1,3-диметил-7-(4-морфолинилметил)-1Н-пурин-2,6-дион(7-морфолинометилтеофиллин), 3,7-дигидро-1-(2-гидроксипропил)-3,7-диметил-1Н-пурин-2,6-дион(протеобромин), 3,7-дигидро-3,7-диметил-1Н-пурин-2,6-дион (теобромин);
(А7с) 6-амино-3-этил-1-(2-пропенил)-2,4-(1Н, 3Н)-пиримидиндион (аминометрадин), 6-амино-3-метил-1-(2-метил-2-пропенил)-2,4-(1Н, 3Н)-пиримидиндион (амизометрадин);
(A7d) N-фенил-1,3,5-триазин-2,4-диамин (аманозин), 3,5-диамино-N-(аминоиминометил)-6-хлорпиразинкарбоксамид (амилорид), N-(4-хлорфенил)-1,3,5-триазин-2,4-диамин (хлоразанил), этиловый эфир [3-метил-4-оксо-5-(1-пиперидинил)-2-тиазолидинилиден] уксусной кислоты (этозолин), 6-гидразино-3-пиридазинкарбоксамид(гидракарбазин), 5-амино-2[1-(3,4-дихлорфенил)этил] -2,4-дигидро-3Н-пиразол-3-он(музолимин), 2-(2,2-дициклогексилэтил) пиперидин (пергекселин), 3-(аминосульфонил)-5-(бутиламино)-4-феноксибензойная кислота (буметанид), 5-(аминосульфонил)-4-хлор-2-[(2-фуранилметил)-амино] бензойная кислота (фуросемид), N-[[(1-метилэтил)амино] карбонил] -4-[(3-метилфенил)амино] -3-пиридинсульфонамид(торасемид).1. Nitrate salts of compounds selected from the following classes:
Class (Alb):
R A1 = -CH 2 OH,
R 1 = H, Cl;
R A1 II = (CH 2 ) 3 -CH 3 , -O-CH 2 -CH 3 ;
R A1 III = H, free valence;
R A1 IV = free valence;
or R A1 = -O and R A1 III = free valence form with a carbon atom in the 5 position keto group,
or R A1 IV , R A1 III , R A1 I and carbon atoms in the 4 and 5 positions of the heterocyclic ring of formula (A1b) form an aromatic ring containing a COOH group (ICC),
or R A1 I , R A1 IV and a carbon atom in the 4 position of the heterocyclic ring of the formula (Alb) form the following saturated ring having five carbon atoms:
when R A1 III = free valence and R A1 IV = free valence is a double bond between carbon atoms in 4 and 5 positions of the heterocyclic ring of formula (Alb),
Class (Alc):
The predecessor of the class (Alc) is known as valsartan;
Class (A2):
1 (2H) -phthalazine nongidrazone (hydralazine); 6- (1-piperidinyl) -2,4-pyrimidinediamine-3-oxide (minoxidil); 1 - [[3- (4,7-dihydro-1-methyl-7-oxo-3-propyl-1H-pyrazole [4,3-d] pyrimidin-5-yl) -4-ethoxyphenyl] sulfonyl] -4 -methyl piperazine (sildenafil), 2- (2-propyloxyphenyl) -8-azapurin-6-one (zaprinast);
Class (A3):
R B1 VI = H
R B1 VII = H
R B1 I and R B1 II are equal or different from each other and mean H, CH 3 ,
R B1 III = H, CH 3 ,
-CH 2 -CH 2 -Y B1 (XIe),
in the formula (XId) t = 0.1;
in the formula (Xle) Y B1 can have the following meanings:
in the formula (XIf), Z = H, -OCH 3 ;
in the formula (A3):
X B1 = -O-, -S-;
n and m are equal or different from each other and are 0, 1;
—CH 2 —CH (OH) —CH 2 —NH — CH (CH 3 ) 2 (XIr),
in the formula (XIr):
S 1 = H, CN, OCH 3 , CH 3 , —CH 2 —CH 3 , —O — CH 2 —COHH — CH 3 , —COCH 3 , —CO— (CH 2 ) 2 —CH 3 , —O- CH 2 -CH = CH 2 , -CH 2 -CH = CH 2 , cyclopentyl or
S 2 = H, CH 3 , Cl, -SOCH 3 , -CONH 2 ;
S 3 = H, F, Cl, OH, NO 2 , —CH 2 —CO — NH 2 , - (CH 2 ) 2 —OCH 3 , —NH-COCH 3 ,
—CH 2 —O — CH 2 —CH 2 —O — CH (CH 3 ) 2 , —CH 2 —CH 2 —COOCH 3 , —NH — CO — N (C 2 H 5 ) 2 ,
-NH-CO- (CH 2 ) 2 -CH 3 , -NH-SO 2 -CH 3 , -NH-CO-NH- [cyclohexyl], -CH 2 -CH 2 -O-CH 2 - [cyclopropyl]; S 4 = H, Cl, —CH 2 —CH 2 - or
S 1 , S 2 and carbon atoms in 2 and 3 positions of the aromatic ring of six carbon atoms of the above-mentioned radical (XIp) form the following ring:
where (*) is an atom located near the aromatic ring of formula XIp VII
B = -CH 2 -, -NH-, -CH-CH-, (*) -CO-CH 2 -;
A = —O—, (*) —CH 2 —CH (OH) -, (*) —O — CH 2 -, (*) —S — CH 2 -, —CH 2 —CH 2 , —CH 2 - ,
W 1 = H, free valence;
W 2 = free valence, H, OH, -CH 3 , -ONO 2 , -O;
or A is a tertiary carbon atom and at the same time W 1 means the free valence to form a double bond -CH = CH- between A and the carbon atom in the 1 'position;
or W 1 , W 2 a carbon atom in the 1 ′ position and A form an aromatic ring having six carbon atoms according to the following formula:
when W 2 = -O and W 1 = free valence with a carbon atom in the 1 ′ position of the radical (XIp VII ) a ketone group is formed;
or when in formula (XIp) S 4 = -CH 2 -CH 2 -, and in formula (A3) X B1 is oxygen, m = n = 1 and R B1 VII = free valence, the next ring with carbon atoms in 1 is formed and 6 position of the aromatic ring of the radical (XIp):
or when in formula (A3) n = m = 1, both R B1 VII and R B1 VI = free valence, S 4 and carbon atoms in 1 and 6 position of the aromatic ring of formula (XIp), S 1 is -CH 2 -CH 3 , together with the carbon atom - | C | n - and X B1 = oxygen of formula (A3) form the following ring:
and, in addition, the following compounds:
2-hydroxy-5- [1-hydroxy-2 - [(1-methyl-3-phenylpropyl) amino] ethyl] benzamide (labetalol), 1- (4-amino-6,7-dimethoxy-2-quinazolinyl) - 4 - [(tetrahydro-2-furanyl) carbonyl] piperazine (terazosin), 1- (4-amino-6,7-dimethoxy-2-quinazolinyl) -4- (2-furanylcarbonyl) piperazine (prazosin);
excluding in formula (A3) the compounds obtained when the substituents of the specified formula have the following meanings:
R B1 I = R B1 II = R B1 III = CH 3 ; R B1 V = H; n = 1; m = 1
R B1 VI = R B1 VII = H, X B1 = 0; R B1 IV = radical XI p , where
S 1 = S 2 = S 4 = H, S 3 = -NH-CO-NH- [cyclohexyl] (talinol);
R B1 I = R B1 II = CH 3 ; n = 1; R B1 III = R B1 V = R B1 VII = R B1 VII = H;
X B1 VI = 0; R B1 IV is an aromatic ring (XI p )
with S 2 = S 3 = S 4 = H, S 1 = -CH 2 -CH-CH 2 (alprenolol)
Class (A4):
(A4a) β - [(2-methylpropoxy) methyl] -N-phenyl-N- (phenylmethyl) -1-pyrrolidine ethanamine (bepridyl), (2S-cis) -3- (acetyloxy) -8-chloro-5- [ 2- (dimethylamino) ethyl] -2,3-dihydro-2- (4-methoxyphenyl) -1,5-benzothiazepin-4 (5H) -one (Clentiazem), (2S-cis) -3- (acetyloxy) - 5- [2- (dimethylamino) ethyl] -2,3-dihydro-2- (4-methoxyphenyl) -1,5-benzothiazepin-4 (5H) -one (diltiazem), γ-phenyl-N- (1- phenylethyl) benzene-propanamine (fendilin), α- [3 - [[2- (3,4-dimethoxyphenyl) ethyl] methylamine] propyl] -3,4,5-trimethoxy-α- (1-methylethyl) -benzeneacetonitrile ( gallopamyl), (1S-cis) methoxyacetic acid-2- [2 [[3- (1H-benzimidazol-2-yl) propyl] methylamino] ethyl] -6-f torus-1,2,3,4-tetrahydro-1- (1-methylethyl) -2-naphthalene ester (mibefradyl), N- (1-methyl-2-phenylethyl) -γ-phenylbenzenepropanamine (prenyl amine), (R) -2- [2- [3 - [[2- (1,3-benzodioxol-5-yloxy) ethyl] methylamino] propoxy] -5-methoxyphenyl] -4-methyl-2H-1,4-benzothiazin-3 ( 4H) -one (semothiadyl), N- (1,1-dimethylethyl) -α-methyl-γ-phenylbenzenepropane-amine (terodilin), α- [3 - [[2- (3,4-dimethoxyphenyl) -ethyl] methyl amino] propyl] -3,4-dimethoxy-α- (1-methylethyl) -benzeneacetonitrile (verapamil);
(A4b) 3-ethyl-5-methyl ester 2 - [(2-aminoethoxy) methyl] -4- (2-chlorophenyl) -1,4-dihydro-6-methyl-3,5-pyridinedicarboxylic acid (amlodipine), 1,4-dihydro-2,6-dimethyl-4- (2-nitrophenyl) -3,5-pyridinedicarboxylic acid methyl aryl-2-oxopropyl ester (aranidipine), methyl 1- (phenylmethyl) -3-pyrrolidinyl ether [S - (R *, R *)] -1,4-dihydro-2,6-dimethyl-4- (3-nitrophenyl) -3,5-pyridinedicarboxylic acid (barnidipine), methyl-1- (phenylmethyl) -3- (R *, R *) - ± -1,4-dihydro-2,6-dimethyl-4- (3-nitrophenyl) -3,5-pyridinedicarboxylic acid piperidinyl ester (benidipine), 2-methoxyethyl-3-phenyl 2-Propenyl ester (E) - ± -1,4-dihydr -2,6-dimethyl-4- (3-nitrophenyl) -3,5-pyridinedicarboxylic acid (cilidipine), 2 [phenyl (phenylmethyl) amino] 5- (5,5-dimethyl-1,3,2-ethyl ester) dioxaphosphorinan-2-yl) -1,4-dihydro-2,6-dimethyl-4- (3-nitrophenyl) -3-pyridine carboxylic acid P-oxide (etonidipine), 2 [[[4-fluorophenyl) methyl] methylamino] ethyl-1-methyl ethyl ester ± -4- (1, 3-benzodioxol-4-yl) -1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylic acid (elgodipin), ethyl methyl ester 4- (2 , 3-dichlorophenyl) -1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylic acid (felodipine), 5-methyl-3- (1-methyl) -ethyl ester 4- (4-benzofurazanyl) - 1,4-dihydro-2,6-d methyl-3,5-pyridinedicarboxylic acid (isradipine), (E) -4- [2- [3- (1,1-dimethylethoxy) -3-oxo-1-propenyl] phenyl] -1,4-dihydro diethyl ether -2,6-dimethyl-3,5-pyridinedicarboxylic acid (lacidipine), 2 - [(3,3-diphenylpropyl) methylamine] -1,1-dimethyl ethyl methyl 1,4-dihydro-2,6-dimethyl-4- (3-nitrophenyl) -3,5-pyridinedicarboxylic acid (lercanidipine), 2- [4- (diphenylmethyl) -1-piperazinyl] ethyl 1,4-dihydro-2,6-dimethyl-4- (3-nitrophenyl) ) -3,5-pyridinedicarboxylic acid (manipipine), methyl-2- [methyl (phenylmethyl) -amino] ethyl ester 1,4-dihydro-2,6-dimethyl-4- (3-nitrophenyl) -3,5- pyridi dicarboxylic acid (nicardipine), 1, 4-dihydro-2,6-dimethyl-4- (2-nitrophenyl) -3,5-pyridinedicarboxylic acid dimethyl ester (nifedipine), 3-methyl-5- (1-methylethyl) ether 2-cyano-1,4-dihydro-6-methyl-4- (3-nitrophenyl) -3,5-pyridinedicarboxylic acid (nilvadipine), 2-methoxyethyl-1-methyl ethyl ester 1,4-dihydro-2,6- dimethyl-4- (3-nitrophenyl) -3,5-pyridinedicarboxylic acid (nimodipine), 1,4-dihydro-2,6-dimethyl-4- (2-nitrophenyl) -3,5- methyl methyl-2-methylpropyl ether pyridine dicarboxylic acid (nizoldipine), 1,4-dihydro-2,6-dimethyl-4- (3-nitrophenyl) -3,5-pyridinedicarboxylic ethyl methyl ester acids (nitrendipine);
(A4c) 1- (diphenylmethyl) -4- (3-phenyl-2-propenyl) piperazine (cinnarizine), (E) -1- [bis (4-fluorophenyl) methyl] -4- (3-phenyl-2- propenyl) piperazine (flunarizin), 4- [4,4-bis (4-fluorophenyl) butyl] -N- (2,6-dimethylphenyl) -1-piperazine acetamide (lidoflazin), 1- [bis (4-fluorophenyl) methyl ] -4 - [(2,3,4-trimethoxyphenyl) methyl] piperazine (lomerizine);
(A4d) N, N-dimethyl-3 - [[1- (phenylmethyl) -cycloheptyl] oxy] -1-propanamine (benciclan), 1- [2- [2- (diethylamino) ethoxy] phenyl] -3-phenyl -1-propanone (etaphenone), 3,4-dimethoxy-N-methyl-N- [3- [4 - [[2- (1-methylethyl) -1-indolizinyl] sulfonyl] phenoxy] propyl] benzene ethanamine (phantofaron );
Class (A7):
(A7a) 6-chloro-3,4-dihydro-3 - [(2-propenylthio) methyl] -2H-1,2,4-benzothiadiazine-7-sulfonamide 1,1-dioxide (althiazide), 3,4- dihydro-3- (phenylmethyl) -6- (trifluoromethyl) -2H-1,2,4-benzothiadiazine-7-sulfonamide 1,1-dioxide (bendroflumethiazide), (6-chloro-3 - [[(phenylmethyl) thio] methyl] -2H-1,2,4-benzothiadiazine-7-sulfonamide-1,1-dioxide (benzthiazide), 6-chloro-3,4-dihydro-3- (phenylmethyl) -2H-1,2,4- Benzothiadiazine-7-sulfonamide 1,1-dioxide (benzylhydrochlorothiazide), 6-chloro-3,4-dihydro-3- (2-methylpropyl) -2H-1,2,4-benzothiadiazin-7-sulfonamide 1,1 -dioxide (butiazid), 6-chloro-2H-1,2,4-benzothiadiazine-7-sulfonamide 1,1-dioxide (chlortia id), 2-chloro-5- (2,3-dihydro-1-hydroxy-3-oxo-1H-isoindol-1-yl) benzobesulfonamide (chlorthalidone), 6-chloro-3- (cyclopentylmethyl) -3,4 -dihydro-2H-1,2,4-benzothiadiazin-7-sulfonamide 1,1-dioxide (cyclopentyazide), 3-bicyclo [2.2.1] -hept-5-ene-2-yl-6-chloro 3,4-dihydro-2H-1,2,4-benzothiadiazine-7-sulfonamide 1,1-dioxide (cyclothiazide), 6-chloro-3,4-dihydro-3 - [[(2,2,2-trifluoroethyl ) thio] methyl] -2H-1,2,4-benzothiadiazine-7-sulfonamide 1,1-dioxide (epithiazide), 6-chloro-3-ethyl-3,4-dihydro-2H-1,2,4- Benzothiadiazine-7-sulfonamide 1,1-dioxide (ethiazide), 7-chloro-1,2,3,4-tetrahydro-4-oxo-2-phenyl-6-quinazoline sulfonamide (fenhizone), 3- (am Osulfonyl) -4-chloro-N- (2,3-dihydro-2-methyl-1H-indole-1-yl) benzamide (indapamide), 6-chloro-3,4-dihydro-2H-1,2,4 -benzothiadiazine-7-sulfonamide 1,1-dioxide (hydrochlorothiazide), 3,4-dihydro-6- (trifluoromethyl) -2H-1,2,4-benzothiadiazine-7-sulfonamide 1,1-dioxide (hydroflumethiazide), 6 -chloro-3- (chloromethyl) -3,4-dihydro-2-methyl-2H-1,2,4-benzothiadiazine-7-sulfonamide 1,1-dioxide (methiclothiazide), 3,4-dihydro-6-methyl -2H-1-benzothiopyran-7-sulfonamide 1,1-dioxide (methicrane), 7-chloro-1,2,3,4-tetrahydro-2-methyl-3- (2-methylphenyl) -4-oxo-6 -quinazolin sulfonamide (metolazone), 6-chloro-3 - [(4-fluorophenyl) -methyl] -3,4-dihydro-2H-1,2,4-benzot adiazin-7-sulfonamide 1,1-dioxide (paraflutizide), 6-chloro-3,4-dihydro-2-methyl-3 - [[(2,2,2-trifluoroethyl) thio] methyl] -2N-1, 2,4-benzothiadiazine-7-sulfonamide 1,1-dioxide (polythiazide), 7-chloro-2-ethyl-1,2,3,4-tetrahydro-4-oxo-6-quinazoline sulfonamide (quintazone), 6-chloro -3,4-dihydro-3-trichloromethyl-2H-1,2,4-benzothiadiazine-7-sulfonamide 1,1-dioxide (texloziaz), 6-chloro-3- (dichloromethyl) -3,4-dihydro-2H -1,2,4-benzothiadiazine-7-sulfonamide 1,1-dioxide (trichloromethiazide);
(A7b) 3,7-dihydro-1,3-dimethyl-7- (4-morpholinylmethyl) -1H-purin-2,6-dione (7-morpholinomethyltheophylline), 3,7-dihydro-1- (2-hydroxypropyl -3,7-dimethyl-1H-purine-2,6-dione (proteobromin), 3,7-dihydro-3,7-dimethyl-1H-purine-2,6-dione (theobromine);
(A7c) 6-amino-3-ethyl-1- (2-propenyl) -2,4- (1H, 3H) -pyrimidinedione (aminometradin), 6-amino-3-methyl-1- (2-methyl-2 -propenyl) -2,4- (1H, 3H) -pyrimidinedione (amisometradine);
(A7d) N-phenyl-1,3,5-triazin-2,4-diamine (amanosin), 3,5-diamino-N- (aminoiminomethyl) -6-chloropyrazinecarboxamide (amiloride), N- (4-chlorophenyl) -1,3,5-triazin-2,4-diamine (chlorazanil), [3-methyl-4-oxo-5- (1-piperidinyl) -2-thiazolidinylidene] acetic acid ethyl ester (etozoline), 6-hydrazino -3-pyridazinecarboxamide (hydracarbazine), 5-amino-2 [1- (3,4-dichlorophenyl) ethyl] -2,4-dihydro-3H-pyrazol-3-one (muzolimine), 2- (2,2- dicyclohexylethyl) piperidine (perhexeline), 3- (aminosulfonyl) -5- (butylamino) -4-phenoxybenzoic acid (bumetanide), 5- (aminosulfonyl) -4-chloro-2 - [(2-furanylmethyl) -amino] benzoic acid ota (Furosemide), N - [[(1-methylethyl) amino] carbonyl] -4 - [(3-methylphenyl) amino] -3-pyridinesulfonamide (Torasemide).
(А4) (2S-цис)-3-(ацетилокси)-5-[2-(диметиламино)этил] -2,3-дигидро-2-(4-метоксифенил)-1,5-бензотиазепин-4(5Н)-он (дилтиазем), α-[3-[[2-(3,4-диметоксифенил)этил] -метиламино] пропил] -3,4-диметокси-α-(1-метилэтил)-бензолацетонитрил(верапамил);
(А4b) 3-этил-5-метиловый эфир 2-[(2-аминоэтокси)метил] -4-(2-хлорфенил)-1,4-дигидро-6-метил-3,5-пиридиндикарбоновой кислоты (амлодипин), этилметиловый эфир 4-(2,3-дихлорфенил)-1,4-дигидро-2,6-диметил-3,5-пиридиндикарбоновой кислоты (фелодипин), 5-метил-3-(1-метил)этиловый эфир 4-(4-бензофуразанил)-1,4-дигидро-2,6-диметил-3,5-пиридиндикарбоновой кислоты (исрадипин), лерканидипин, метил-2[метил(фенилметил)амино] этиловый эфир 1,4-дигидро-2,6-диметил-4-(3-нитро-фенил)-3,5-пиридиндикарбоновой кислоты (никардипин), диметиловый эфир 1,4-дигидро-2,6-диметил-4-(2-нитрофенил)-3,5-пиридиндикарбоновой кислоты (нифедипин), 2-метоксиэтил-1-метилэтиловый эфир 1,4-дигидро-2,6-диметил-4-(3-нитрофенил)-3,5-пиридиндикарбоновой кислоты (нимодипин), метил-2-метилпропиловый эфир 1,4-дигидро-2,6-диметил-4-(2-нитрофенил)-3,5-пиридиндикарбоновой кислоты (нисолдипин), этилметиловый эфир 1,4-дигидро-2,6-диметил-4-(3-нитрофенил)-3,5-пиридиндикарбоновой кислоты (нитрендипин);
(А4с) (Е)-1-[бис(4-фторфенил)метил] -4-(3-фенил-2-пропенил)пиперазин (флунаризин).4. Nitrate salts according to claim 1 of the following compounds of class
(A4) (2S-cis) -3- (acetyloxy) -5- [2- (dimethylamino) ethyl] -2,3-dihydro-2- (4-methoxyphenyl) -1,5-benzothiazepin-4 (5H) -one (diltiazem), α- [3 - [[2- (3,4-dimethoxyphenyl) ethyl] methylamino] propyl] -3,4-dimethoxy-α- (1-methylethyl) benzene acetonitrile (verapamil);
(A4b) 3-ethyl-5-methyl ester 2 - [(2-aminoethoxy) methyl] -4- (2-chlorophenyl) -1,4-dihydro-6-methyl-3,5-pyridinedicarboxylic acid (amlodipine), 4- (2,3-dichlorophenyl) -1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylic acid ethyl methyl ester (felodipine), 4- (1-methyl) ethyl ester ( 4-benzofurazanil) -1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylic acid (isradipine), lercanidipine, methyl-2 [methyl (phenylmethyl) amino] ethyl ester 1,4-dihydro-2,6 -dimethyl-4- (3-nitrophenyl) -3,5-pyridinedicarboxylic acid (nicardipine), 1,4-dihydro-2,6-dimethyl-4- (2-nitrophenyl) -3,5-pyridine dimethyl ester rboxylic acid (nifedipine), 1,4-dihydro-2,6-dimethyl-4- (3-nitrophenyl) -3,5-pyridinedicarboxylic acid (2-methoxyethyl-1-methylethyl ester) (methyl-2-methylpropyl ester) 1,4-dihydro-2,6-dimethyl-4- (2-nitrophenyl) -3,5-pyridinedicarboxylic acid (nisoldipine), 1,4-dihydro-2,6-dimethyl-4- (3-nitrophenyl ethyl methyl ester -3,5-pyridinedicarboxylic acid (nitrendipine);
(A4c) (E) -1- [bis (4-fluorophenyl) methyl] -4- (3-phenyl-2-propenyl) piperazine (flunarizin).
(А7а) 6-хлор-2Н-1,2,4-бензотиадиазин-7-сульфонамид-1,1-диоксид(хлортиазид), 2-хлор-5-(2,3-дигидро-1-гидрокси-3-оксо-1Н-изоиндол-1-ил)бензобесульфонамид (хлорталидон), 6-хлор-3,4-дигидро-2Н-1,2,4-бензотиадиазин-7-сульфонамид 1,1-диоксид(гидрохлортиазид), 3-(аминосульфонил)-4-xnop-N-(2,3-дигидро-2-метил-1Н-индол-1-ил)бензамид (индапамид), 7-хлор-1,2,3,4-тетрагидро-2-метил-3-(2-метилфенил)-4-оксо-6-хиназолинсульфонамид(метолазон), 7-хлор-2-этил-1,2,3,4-тетрагидро-4-оксо-6-хиназолинсульфонамид (хинетазон) ;
(A7d) 3,5-диамино-N-(аминоиминометил)-6-хлорпиразинкарбоксамид (амилорид), 6-фенил-2,4,7-птеридинтриамин (триамтерен), 3-(аминосульфонил)-5-(бутиламино)-4-феноксибензойная кислота (буметанид), 5-(аминосульфонил)-4-хлор-2-[(2-фуранилметил)амино] бензойная кислота (фуросемид), N-[[(1-метилэтил)амино] -карбонил] -4-[(3-метилфенил)амино] -3-пиридинсульфонамид (торасемид).5. Nitrate salts according to claim 1 of the following compounds of class (A7):
(A7a) 6-chloro-2H-1,2,4-benzothiadiazine-7-sulfonamide-1,1-dioxide (chlorothiazide), 2-chloro-5- (2,3-dihydro-1-hydroxy-3-oxo -1H-isoindol-1-yl) benzobesulphonamide (chlorothalidone), 6-chloro-3,4-dihydro-2H-1,2,4-benzothiadiazine-7-sulfonamide 1,1-dioxide (hydrochlorothiazide), 3- (aminosulphonyl ) -4-xnop-N- (2,3-dihydro-2-methyl-1H-indol-1-yl) benzamide (indapamide), 7-chloro-1,2,3,4-tetrahydro-2-methyl- 3- (2-methylphenyl) -4-oxo-6-quinazolin sulfonamide (metolazone), 7-chloro-2-ethyl-1,2,3,4-tetrahydro-4-oxo-6-quinazolin sulfonamide (quine tazone);
(A7d) 3,5-diamino-N- (aminoiminomethyl) -6-chloropyrazinecarboxamide (amiloride), 6-phenyl-2,4,7-pteridine triamine (triamterene), 3- (aminosulfonyl) -5- (butylamino) -4 -phenoxybenzoic acid (bumetanide), 5- (aminosulfonyl) -4-chloro-2 - [(2-furanylmethyl) amino] benzoic acid (furosemide), N - [[[(1-methylethyl) amino] -carbonyl] -4- [(3-methylphenyl) amino] -3-pyridinesulfonamide (torasemide).
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1998
- 1998-06-19 IT IT1998MI001408A patent/IT1301759B1/en active IP Right Grant
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1999
- 1999-06-15 CA CA002335356A patent/CA2335356A1/en not_active Abandoned
- 1999-06-15 KR KR10-2000-7014179A patent/KR100460714B1/en not_active IP Right Cessation
- 1999-06-15 AU AU45139/99A patent/AU770387B2/en not_active Ceased
- 1999-06-15 ES ES99927990T patent/ES2234265T3/en not_active Expired - Lifetime
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- 1999-06-15 HU HU0102719A patent/HUP0102719A3/en unknown
- 1999-06-15 JP JP2000555885A patent/JP2002518492A/en active Pending
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- 1999-06-15 CN CN99807516A patent/CN1315945A/en active Pending
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- 1999-06-15 AT AT99927990T patent/ATE282600T1/en not_active IP Right Cessation
- 1999-06-15 US US09/719,164 patent/US6645965B1/en not_active Expired - Fee Related
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- 1999-06-15 EP EP99927990A patent/EP1087953B1/en not_active Expired - Lifetime
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