NO323553B1 - Fremgangsmate for tilvirkning og bruk av pyrrolopyrimidinon-derivater - Google Patents
Fremgangsmate for tilvirkning og bruk av pyrrolopyrimidinon-derivater Download PDFInfo
- Publication number
- NO323553B1 NO323553B1 NO20023823A NO20023823A NO323553B1 NO 323553 B1 NO323553 B1 NO 323553B1 NO 20023823 A NO20023823 A NO 20023823A NO 20023823 A NO20023823 A NO 20023823A NO 323553 B1 NO323553 B1 NO 323553B1
- Authority
- NO
- Norway
- Prior art keywords
- ch2ch2ch3
- pyrrolo
- dihydro
- ylsulfonyl
- pyrimidin
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 16
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- DXVAQZJPPDWTNY-UHFFFAOYSA-N pyrrolo[3,2-d]pyrimidin-2-one Chemical class O=C1N=CC2=NC=CC2=N1 DXVAQZJPPDWTNY-UHFFFAOYSA-N 0.000 title abstract description 3
- 230000008569 process Effects 0.000 title description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 20
- 125000005843 halogen group Chemical group 0.000 claims abstract description 15
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 1069
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 884
- 150000001875 compounds Chemical class 0.000 claims description 614
- 238000002360 preparation method Methods 0.000 claims description 249
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 232
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 202
- -1 hydrates) thereof Chemical class 0.000 claims description 152
- 239000000460 chlorine Substances 0.000 claims description 52
- 239000000203 mixture Substances 0.000 claims description 50
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 28
- FJTLWOWJNQINPG-UHFFFAOYSA-N 2-[2-ethoxy-5-(4-methylpiperazin-1-yl)sulfonylphenyl]-5-methyl-7-propyl-1h-pyrrolo[3,2-d]pyrimidin-4-one Chemical compound CCCC1=CN(C)C(C(N2)=O)=C1N=C2C(C(=CC=1)OCC)=CC=1S(=O)(=O)N1CCN(C)CC1 FJTLWOWJNQINPG-UHFFFAOYSA-N 0.000 claims description 21
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 18
- 150000003839 salts Chemical class 0.000 claims description 15
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 10
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 9
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 8
- FQUYSHZXSKYCSY-UHFFFAOYSA-N 1,4-diazepane Chemical compound C1CNCCNC1 FQUYSHZXSKYCSY-UHFFFAOYSA-N 0.000 claims description 7
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 7
- 150000003536 tetrazoles Chemical group 0.000 claims description 7
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 6
- VSLLATHRSSWKIO-UHFFFAOYSA-N 2-[2-ethoxy-5-[4-(3-fluoropropyl)piperazin-1-yl]sulfonylphenyl]-5-ethyl-7-propyl-1h-pyrrolo[3,2-d]pyrimidin-4-one Chemical compound CCCC1=CN(CC)C(C(N2)=O)=C1N=C2C(C(=CC=1)OCC)=CC=1S(=O)(=O)N1CCN(CCCF)CC1 VSLLATHRSSWKIO-UHFFFAOYSA-N 0.000 claims description 6
- ODJWZRHGGAYUGR-UHFFFAOYSA-N 2-[2-ethoxy-5-[4-(3-fluoropropyl)piperazin-1-yl]sulfonylphenyl]-5-methyl-7-propyl-1h-pyrrolo[3,2-d]pyrimidin-4-one Chemical compound CCCC1=CN(C)C(C(N2)=O)=C1N=C2C(C(=CC=1)OCC)=CC=1S(=O)(=O)N1CCN(CCCF)CC1 ODJWZRHGGAYUGR-UHFFFAOYSA-N 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 201000010099 disease Diseases 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- 125000004193 piperazinyl group Chemical group 0.000 claims description 6
- 238000011282 treatment Methods 0.000 claims description 6
- 206010002383 Angina Pectoris Diseases 0.000 claims description 5
- 206010019280 Heart failures Diseases 0.000 claims description 5
- 206010020772 Hypertension Diseases 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- 150000004820 halides Chemical group 0.000 claims description 5
- 201000001881 impotence Diseases 0.000 claims description 5
- TUACHMTXIBSUTC-UHFFFAOYSA-N 2-[2-ethoxy-5-(4-propan-2-ylpiperazin-1-yl)sulfonylphenyl]-5-methyl-7-propyl-1h-pyrrolo[3,2-d]pyrimidin-4-one Chemical compound CCCC1=CN(C)C(C(N2)=O)=C1N=C2C(C(=CC=1)OCC)=CC=1S(=O)(=O)N1CCN(C(C)C)CC1 TUACHMTXIBSUTC-UHFFFAOYSA-N 0.000 claims description 4
- MFKQFAQDTGMLFV-UHFFFAOYSA-N 2-[2-ethoxy-5-(4-propylpiperazin-1-yl)sulfonylphenyl]-5-methyl-7-propyl-1h-pyrrolo[3,2-d]pyrimidin-4-one Chemical compound C1CN(CCC)CCN1S(=O)(=O)C1=CC=C(OCC)C(C=2NC(=O)C=3N(C)C=C(CCC)C=3N=2)=C1 MFKQFAQDTGMLFV-UHFFFAOYSA-N 0.000 claims description 4
- JSIMDOXAAVNYGX-UHFFFAOYSA-N 2-[2-ethoxy-5-[4-(2-hydroxyethyl)piperazin-1-yl]sulfonylphenyl]-5-methyl-7-propyl-1h-pyrrolo[3,2-d]pyrimidin-4-one Chemical compound CCCC1=CN(C)C(C(N2)=O)=C1N=C2C(C(=CC=1)OCC)=CC=1S(=O)(=O)N1CCN(CCO)CC1 JSIMDOXAAVNYGX-UHFFFAOYSA-N 0.000 claims description 4
- URHNZNLBOBJKFB-UHFFFAOYSA-N 2-[2-ethoxy-5-[4-(3-fluoropropyl)piperazin-1-yl]sulfonylphenyl]-5-ethyl-7-(3-fluoropropyl)-1h-pyrrolo[3,2-d]pyrimidin-4-one Chemical compound C1=C(C=2NC(=O)C=3N(CC)C=C(CCCF)C=3N=2)C(OCC)=CC=C1S(=O)(=O)N1CCN(CCCF)CC1 URHNZNLBOBJKFB-UHFFFAOYSA-N 0.000 claims description 4
- GRUCRVOYOIRNJK-UHFFFAOYSA-N 2-[5-[4-(2-fluoroethyl)piperazin-1-yl]sulfonyl-2-propoxyphenyl]-5-methyl-7-propyl-1h-pyrrolo[3,2-d]pyrimidin-4-one Chemical compound C1=C(C=2NC(=O)C=3N(C)C=C(CCC)C=3N=2)C(OCCC)=CC=C1S(=O)(=O)N1CCN(CCF)CC1 GRUCRVOYOIRNJK-UHFFFAOYSA-N 0.000 claims description 4
- LLPKTRRLHVTFAL-UHFFFAOYSA-N 2-[5-[4-(2-hydroxyethyl)piperazin-1-yl]sulfonyl-2-propoxyphenyl]-5-methyl-7-propyl-1h-pyrrolo[3,2-d]pyrimidin-4-one Chemical compound C1=C(C=2NC(=O)C=3N(C)C=C(CCC)C=3N=2)C(OCCC)=CC=C1S(=O)(=O)N1CCN(CCO)CC1 LLPKTRRLHVTFAL-UHFFFAOYSA-N 0.000 claims description 4
- DJKLFULWPWSTCS-UHFFFAOYSA-N 2-[5-[4-(3-hydroxypropyl)piperazin-1-yl]sulfonyl-2-propoxyphenyl]-5-methyl-7-propyl-1h-pyrrolo[3,2-d]pyrimidin-4-one Chemical compound C1=C(C=2NC(=O)C=3N(C)C=C(CCC)C=3N=2)C(OCCC)=CC=C1S(=O)(=O)N1CCN(CCCO)CC1 DJKLFULWPWSTCS-UHFFFAOYSA-N 0.000 claims description 4
- OGGZBFFDKPIXRU-UHFFFAOYSA-N 5-methyl-2-[5-(4-methylpiperazin-1-yl)sulfonyl-2-propoxyphenyl]-7-propyl-1h-pyrrolo[3,2-d]pyrimidin-4-one Chemical compound C1=C(C=2NC(=O)C=3N(C)C=C(CCC)C=3N=2)C(OCCC)=CC=C1S(=O)(=O)N1CCN(C)CC1 OGGZBFFDKPIXRU-UHFFFAOYSA-N 0.000 claims description 4
- 206010003210 Arteriosclerosis Diseases 0.000 claims description 4
- 208000011775 arteriosclerosis disease Diseases 0.000 claims description 4
- 210000004204 blood vessel Anatomy 0.000 claims description 4
- 150000004677 hydrates Chemical class 0.000 claims description 4
- MIJFNYMSCFYZNY-UHFFFAOYSA-N mirodenafil Chemical compound C1=C(C=2NC=3C(CCC)=CN(CC)C=3C(=O)N=2)C(OCCC)=CC=C1S(=O)(=O)N1CCN(CCO)CC1 MIJFNYMSCFYZNY-UHFFFAOYSA-N 0.000 claims description 4
- 239000002243 precursor Substances 0.000 claims description 4
- 208000012201 sexual and gender identity disease Diseases 0.000 claims description 4
- 208000015891 sexual disease Diseases 0.000 claims description 4
- ICWLLWVOTYQYGL-UHFFFAOYSA-N 2-[1-[3-(5-methyl-4-oxo-7-propyl-1h-pyrrolo[3,2-d]pyrimidin-2-yl)-4-propoxyphenyl]sulfonylpiperidin-4-yl]acetic acid Chemical compound C1=C(C=2NC(=O)C=3N(C)C=C(CCC)C=3N=2)C(OCCC)=CC=C1S(=O)(=O)N1CCC(CC(O)=O)CC1 ICWLLWVOTYQYGL-UHFFFAOYSA-N 0.000 claims description 3
- VCEVXPFWXARWFX-UHFFFAOYSA-N 2-[1-[4-ethoxy-3-(5-methyl-4-oxo-7-propyl-1h-pyrrolo[3,2-d]pyrimidin-2-yl)phenyl]sulfonylpiperidin-4-yl]acetic acid Chemical compound CCCC1=CN(C)C(C(N2)=O)=C1N=C2C(C(=CC=1)OCC)=CC=1S(=O)(=O)N1CCC(CC(O)=O)CC1 VCEVXPFWXARWFX-UHFFFAOYSA-N 0.000 claims description 3
- HRMUWEKIUCWEKJ-UHFFFAOYSA-N 2-[2-ethoxy-5-(4-ethylpiperazin-1-yl)sulfonylphenyl]-5-ethyl-7-(3-fluoropropyl)-1h-pyrrolo[3,2-d]pyrimidin-4-one Chemical compound C1=C(C=2NC(=O)C=3N(CC)C=C(CCCF)C=3N=2)C(OCC)=CC=C1S(=O)(=O)N1CCN(CC)CC1 HRMUWEKIUCWEKJ-UHFFFAOYSA-N 0.000 claims description 3
- JHMMVYUDBXMOQC-UHFFFAOYSA-N 2-[2-ethoxy-5-(4-propan-2-ylpiperazin-1-yl)sulfonylphenyl]-5-ethyl-7-(3-fluoropropyl)-1h-pyrrolo[3,2-d]pyrimidin-4-one Chemical compound C1=C(C=2NC(=O)C=3N(CC)C=C(CCCF)C=3N=2)C(OCC)=CC=C1S(=O)(=O)N1CCN(C(C)C)CC1 JHMMVYUDBXMOQC-UHFFFAOYSA-N 0.000 claims description 3
- IREAERHSLFXXKN-UHFFFAOYSA-N 2-[2-ethoxy-5-(4-propan-2-ylpiperazin-1-yl)sulfonylphenyl]-5-ethyl-7-propyl-1h-pyrrolo[3,2-d]pyrimidin-4-one Chemical compound CCCC1=CN(CC)C(C(N2)=O)=C1N=C2C(C(=CC=1)OCC)=CC=1S(=O)(=O)N1CCN(C(C)C)CC1 IREAERHSLFXXKN-UHFFFAOYSA-N 0.000 claims description 3
- POSRUULABMZFQX-UHFFFAOYSA-N 2-[2-ethoxy-5-[4-(2-fluoroethyl)piperazin-1-yl]sulfonylphenyl]-5-methyl-7-propyl-1h-pyrrolo[3,2-d]pyrimidin-4-one Chemical compound CCCC1=CN(C)C(C(N2)=O)=C1N=C2C(C(=CC=1)OCC)=CC=1S(=O)(=O)N1CCN(CCF)CC1 POSRUULABMZFQX-UHFFFAOYSA-N 0.000 claims description 3
- KSAJOMXYMWSSNL-UHFFFAOYSA-N 2-[2-ethoxy-5-[4-(2-hydroxyethyl)piperazin-1-yl]sulfonylphenyl]-5-ethyl-7-(3-fluoropropyl)-1h-pyrrolo[3,2-d]pyrimidin-4-one Chemical compound C1=C(C=2NC(=O)C=3N(CC)C=C(CCCF)C=3N=2)C(OCC)=CC=C1S(=O)(=O)N1CCN(CCO)CC1 KSAJOMXYMWSSNL-UHFFFAOYSA-N 0.000 claims description 3
- BKNSVLUMNDNHBN-UHFFFAOYSA-N 2-[2-ethoxy-5-[4-(2-hydroxyethyl)piperazin-1-yl]sulfonylphenyl]-5-ethyl-7-propyl-1h-pyrrolo[3,2-d]pyrimidin-4-one Chemical compound CCCC1=CN(CC)C(C(N2)=O)=C1N=C2C(C(=CC=1)OCC)=CC=1S(=O)(=O)N1CCN(CCO)CC1 BKNSVLUMNDNHBN-UHFFFAOYSA-N 0.000 claims description 3
- PFXDCYNRZNMBSU-UHFFFAOYSA-N 2-[2-ethoxy-5-[4-(2h-tetrazol-5-ylmethyl)piperazin-1-yl]sulfonylphenyl]-5-methyl-7-propyl-1h-pyrrolo[3,2-d]pyrimidin-4-one Chemical compound CCCC1=CN(C)C(C(N2)=O)=C1N=C2C(C(=CC=1)OCC)=CC=1S(=O)(=O)N(CC1)CCN1CC1=NN=NN1 PFXDCYNRZNMBSU-UHFFFAOYSA-N 0.000 claims description 3
- BRYMONKFXAUHNH-UHFFFAOYSA-N 2-[2-ethoxy-5-[4-(3-fluoropropyl)piperazin-1-yl]sulfonylphenyl]-5,7-diethyl-1h-pyrrolo[3,2-d]pyrimidin-4-one Chemical compound C1=C(C=2NC(=O)C=3N(CC)C=C(CC)C=3N=2)C(OCC)=CC=C1S(=O)(=O)N1CCN(CCCF)CC1 BRYMONKFXAUHNH-UHFFFAOYSA-N 0.000 claims description 3
- DIAOTEHYNHEVSJ-UHFFFAOYSA-N 2-[2-ethoxy-5-[4-(3-fluoropropyl)piperazin-1-yl]sulfonylphenyl]-7-ethyl-5-methyl-1h-pyrrolo[3,2-d]pyrimidin-4-one Chemical compound C1=C(C=2NC(=O)C=3N(C)C=C(CC)C=3N=2)C(OCC)=CC=C1S(=O)(=O)N1CCN(CCCF)CC1 DIAOTEHYNHEVSJ-UHFFFAOYSA-N 0.000 claims description 3
- YGEVXUJCUZBZEO-UHFFFAOYSA-N 2-[5-[4-(3-fluoropropyl)piperazin-1-yl]sulfonyl-2-propoxyphenyl]-5-methyl-7-propyl-1h-pyrrolo[3,2-d]pyrimidin-4-one Chemical compound C1=C(C=2NC(=O)C=3N(C)C=C(CCC)C=3N=2)C(OCCC)=CC=C1S(=O)(=O)N1CCN(CCCF)CC1 YGEVXUJCUZBZEO-UHFFFAOYSA-N 0.000 claims description 3
- UXMPKPGEIPZCRK-UHFFFAOYSA-N 3-[1-[3-(5-methyl-4-oxo-7-propyl-1h-pyrrolo[3,2-d]pyrimidin-2-yl)-4-propoxyphenyl]sulfonylpiperidin-4-yl]propanoic acid Chemical compound C1=C(C=2NC(=O)C=3N(C)C=C(CCC)C=3N=2)C(OCCC)=CC=C1S(=O)(=O)N1CCC(CCC(O)=O)CC1 UXMPKPGEIPZCRK-UHFFFAOYSA-N 0.000 claims description 3
- JQDXYVPEEHFJSY-UHFFFAOYSA-N 3-[1-[4-ethoxy-3-(5-methyl-4-oxo-7-propyl-1h-pyrrolo[3,2-d]pyrimidin-2-yl)phenyl]sulfonylpiperidin-4-yl]propanoic acid Chemical compound CCCC1=CN(C)C(C(N2)=O)=C1N=C2C(C(=CC=1)OCC)=CC=1S(=O)(=O)N1CCC(CCC(O)=O)CC1 JQDXYVPEEHFJSY-UHFFFAOYSA-N 0.000 claims description 3
- ZRUMYMURBUPBRB-UHFFFAOYSA-N 5-ethyl-2-[5-(4-ethylpiperazin-1-yl)sulfonyl-2-propoxyphenyl]-7-(3-fluoropropyl)-1h-pyrrolo[3,2-d]pyrimidin-4-one Chemical compound C1=C(C=2NC(=O)C=3N(CC)C=C(CCCF)C=3N=2)C(OCCC)=CC=C1S(=O)(=O)N1CCN(CC)CC1 ZRUMYMURBUPBRB-UHFFFAOYSA-N 0.000 claims description 3
- YNRTZQZINSODAY-UHFFFAOYSA-N 5-ethyl-7-(3-fluoropropyl)-2-[5-[4-(2-hydroxyethyl)piperazin-1-yl]sulfonyl-2-propoxyphenyl]-1h-pyrrolo[3,2-d]pyrimidin-4-one Chemical compound C1=C(C=2NC(=O)C=3N(CC)C=C(CCCF)C=3N=2)C(OCCC)=CC=C1S(=O)(=O)N1CCN(CCO)CC1 YNRTZQZINSODAY-UHFFFAOYSA-N 0.000 claims description 3
- NYBQSRBDMFIPOA-UHFFFAOYSA-N 5-ethyl-7-(3-fluoropropyl)-2-[5-[4-(3-fluoropropyl)piperazin-1-yl]sulfonyl-2-propoxyphenyl]-1h-pyrrolo[3,2-d]pyrimidin-4-one Chemical compound C1=C(C=2NC(=O)C=3N(CC)C=C(CCCF)C=3N=2)C(OCCC)=CC=C1S(=O)(=O)N1CCN(CCCF)CC1 NYBQSRBDMFIPOA-UHFFFAOYSA-N 0.000 claims description 3
- LQISCLODZKORSE-UHFFFAOYSA-N 5-methyl-2-[2-propoxy-5-[4-[2-(2h-tetrazol-5-yl)ethyl]piperazin-1-yl]sulfonylphenyl]-7-propyl-1h-pyrrolo[3,2-d]pyrimidin-4-one Chemical compound C1=C(C=2NC(=O)C=3N(C)C=C(CCC)C=3N=2)C(OCCC)=CC=C1S(=O)(=O)N(CC1)CCN1CCC1=NN=NN1 LQISCLODZKORSE-UHFFFAOYSA-N 0.000 claims description 3
- ITXYIRNYVLGLJX-UHFFFAOYSA-N 7-(cyclopropylmethyl)-2-[2-ethoxy-5-[4-(3-fluoropropyl)piperazin-1-yl]sulfonylphenyl]-5-methyl-1h-pyrrolo[3,2-d]pyrimidin-4-one Chemical compound CCOC1=CC=C(S(=O)(=O)N2CCN(CCCF)CC2)C=C1C(NC(=O)C=1N(C)C=2)=NC=1C=2CC1CC1 ITXYIRNYVLGLJX-UHFFFAOYSA-N 0.000 claims description 3
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- HNEGJTWNOOWEMH-UHFFFAOYSA-N 1-fluoropropane Chemical group [CH2]CCF HNEGJTWNOOWEMH-UHFFFAOYSA-N 0.000 claims description 2
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-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/08—Vasodilators for multiple indications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Pulmonology (AREA)
- Ophthalmology & Optometry (AREA)
- Reproductive Health (AREA)
- Endocrinology (AREA)
- Urology & Nephrology (AREA)
- Gynecology & Obstetrics (AREA)
- Immunology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Vascular Medicine (AREA)
- Hospice & Palliative Care (AREA)
- Otolaryngology (AREA)
- Pregnancy & Childbirth (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrrole Compounds (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR20000007625A KR100358083B1 (ko) | 2000-02-17 | 2000-02-17 | 피롤로피리미디논 유도체와 이의 제조방법, 그리고 이의용도 |
PCT/KR2001/000227 WO2001060825A1 (en) | 2000-02-17 | 2001-02-15 | Pyrrolopyrimidinone derivatives, process of preparation and use |
Publications (3)
Publication Number | Publication Date |
---|---|
NO20023823D0 NO20023823D0 (no) | 2002-08-13 |
NO20023823L NO20023823L (no) | 2002-10-09 |
NO323553B1 true NO323553B1 (no) | 2007-06-11 |
Family
ID=19647449
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO20023823A NO323553B1 (no) | 2000-02-17 | 2002-08-13 | Fremgangsmate for tilvirkning og bruk av pyrrolopyrimidinon-derivater |
Country Status (23)
Country | Link |
---|---|
US (1) | US6962911B2 (es) |
EP (1) | EP1257553B1 (es) |
JP (1) | JP4845076B2 (es) |
KR (1) | KR100358083B1 (es) |
CN (1) | CN1312153C (es) |
AT (1) | ATE267829T1 (es) |
AU (2) | AU2001236140B9 (es) |
BR (1) | BRPI0108395B8 (es) |
CA (1) | CA2400268C (es) |
DE (1) | DE60103508T2 (es) |
DK (1) | DK1257553T3 (es) |
ES (1) | ES2222344T3 (es) |
HU (1) | HU230344B1 (es) |
IL (2) | IL151234A0 (es) |
MX (1) | MXPA02007942A (es) |
NO (1) | NO323553B1 (es) |
NZ (1) | NZ520842A (es) |
PL (1) | PL210796B1 (es) |
PT (1) | PT1257553E (es) |
RU (1) | RU2263676C2 (es) |
TR (1) | TR200402101T4 (es) |
WO (1) | WO2001060825A1 (es) |
ZA (1) | ZA200206587B (es) |
Families Citing this family (38)
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KR100358083B1 (ko) * | 2000-02-17 | 2002-10-25 | 에스케이케미칼주식회사 | 피롤로피리미디논 유도체와 이의 제조방법, 그리고 이의용도 |
EP1362858A1 (en) * | 2002-05-15 | 2003-11-19 | SK Chemicals Co., Ltd. | Pyrrolopyrimidinone derivates, process of preparation and use |
DE10229778A1 (de) * | 2002-07-03 | 2004-01-29 | Bayer Ag | Neue Verwendung von Imidazotriazinonen |
FR2842809A1 (fr) * | 2002-07-26 | 2004-01-30 | Greenpharma Sas | NOUVELLES PYRAZOLO[1,5-a]-1,3,5-TRIAZINES SUBSTITUEES ET LEURS ANALOGUES, COMPOSITIONS PHARMACEUTIQUES LES CONTENANT, UTILISATION A TITRE DE MEDICAMENT ET PROCEDES POUR LEUR PREPARATION |
CN100374441C (zh) * | 2003-06-06 | 2008-03-12 | 天津倍方科技发展有限公司 | 二氢吡咯[2,3-d]嘧啶-4-酮衍生物,其制备方法及其制药用途 |
TW200745106A (en) * | 2005-10-03 | 2007-12-16 | Astrazeneca Ab | Chemical compounds |
KR20080003599A (ko) * | 2006-07-03 | 2008-01-08 | 에스케이케미칼주식회사 | 피롤로피리미디논 유도체의 겐티세이트 염 및 이의제조방법 |
ES2610398T3 (es) * | 2006-07-03 | 2017-04-27 | Sk Chemicals, Co., Ltd. | Sales de derivados de pirrolopirimidinona y procedimiento para su preparación |
KR101002490B1 (ko) * | 2007-06-09 | 2010-12-17 | 동아제약주식회사 | 유데나필을 유효성분으로 함유하는 만성 심부전증 치료용약학적 조성물 |
MX358697B (es) | 2009-10-16 | 2018-08-31 | Melinta Therapeutics Inc | Compuestos antimicrobianos y metodos para fabricar y utilizar los mismos. |
US9193731B2 (en) | 2009-10-16 | 2015-11-24 | Melinta Therapeutics, Inc. | Antimicrobial compounds and methods of making and using the same |
JP6274723B2 (ja) | 2009-10-16 | 2018-02-07 | メリンタ セラピューティクス,インコーポレイテッド | 抗微生物性化合物および抗微生物性化合物の製造方法および使用方法 |
KR101377178B1 (ko) | 2010-04-05 | 2014-03-26 | 에스케이케미칼주식회사 | Pde5 억제제를 함유하는 피부 주름 개선용 조성물 |
CN102372730B (zh) * | 2010-08-19 | 2014-03-26 | 山东轩竹医药科技有限公司 | 桥环取代的磷酸二酯酶抑制剂 |
CN102134242B (zh) * | 2011-01-21 | 2013-08-28 | 浙江大德药业集团有限公司 | 一种用于治疗阳痿的快速长效的化合物 |
TWI490220B (zh) * | 2011-04-04 | 2015-07-01 | Sk Chemicals Co Ltd | 包含pde5抑制劑之用於減少皮膚皺紋之組成物 |
EA201391536A1 (ru) * | 2011-04-15 | 2014-08-29 | Мелинта Терапьютикс, Инк. | Противомикробные соединения и способы их получения и применения |
CN103826638B (zh) * | 2011-09-09 | 2015-11-25 | Sk化学公司 | 含有pde5 抑制剂的减少皮肤皱纹的组合物 |
US9750743B2 (en) | 2012-12-04 | 2017-09-05 | Aribio Inc. | Composition comprising phosphodiesterase type 5 inhibitor for inhibiting apoptosis of nerve cells |
WO2015035426A1 (en) | 2013-09-09 | 2015-03-12 | Melinta Therapeutics, Inc. | Antimicrobial compunds and methods of making and using the same |
MX2016003046A (es) | 2013-09-09 | 2016-09-08 | Melinta Therapeutics Inc | Compuestos antimicrobianos y métodos de fabricación y utilización de los mismos. |
JP2018507881A (ja) | 2015-03-11 | 2018-03-22 | メリンタ セラピューティクス,インコーポレイテッド | 抗微生物化合物ならびにこれらを作製および使用する方法 |
CN104744478B (zh) * | 2015-03-20 | 2016-08-24 | 中国人民解放军第二军医大学 | 一种防治辐射损伤的化合物、单晶及其制备方法和应用 |
US10570137B2 (en) * | 2015-11-16 | 2020-02-25 | Topadur Pharma Ag | 2-phenyl-3,4-dihydropyrrolo[2,1 -F] [1,2,4]triazinone derivatives as phosphodiesterase inhibitors and uses thereof |
BR112019024300A2 (pt) * | 2017-05-22 | 2020-06-16 | Topadur Pharma Ag | Ativadores de guanilato ciclase solúvel com modo duplo de ação e inibidores da fosfodiesterase e usos dos mesmos |
CN112566670A (zh) | 2018-08-06 | 2021-03-26 | 尼科斯股份有限公司 | 一氧化氮释放第5型磷酸二酯酶抑制剂 |
JP2022509815A (ja) | 2018-11-28 | 2022-01-24 | トパデュール ファルマ アーゲー | 新規の二重作用型可溶性グアニル酸シクラーゼ活性化剤およびホスホジエステラーゼ阻害剤とその使用法 |
KR102271305B1 (ko) | 2020-05-21 | 2021-06-30 | 주식회사 아리바이오 | 치매 예방 및 치료용 조성물 |
WO2021245192A1 (en) | 2020-06-04 | 2021-12-09 | Topadur Pharma Ag | Novel dual mode of action soluble guanylate cyclase activators and phosphodiesterase inhibitors and uses thereof |
CN111825593B (zh) * | 2020-08-19 | 2023-04-07 | 上海成澄科技有限公司 | 3-氨基吡咯-2-甲酰胺类化合物的合成方法 |
KR102272907B1 (ko) | 2020-11-05 | 2021-07-05 | 주식회사 아리바이오 | 치매 예방 및 치료용 조성물 |
KR102272910B1 (ko) | 2021-01-28 | 2021-07-06 | 주식회사 아리바이오 | 당뇨병을 동반한 치매 예방 및 치료용 조성물 |
KR20220140960A (ko) | 2021-04-12 | 2022-10-19 | 주식회사 아리바이오 | 당뇨병을 동반한 치매 예방 및 치료용 조성물 |
KR20220146095A (ko) | 2021-04-23 | 2022-11-01 | 주식회사 아리바이오 | Pde5 억제제와 글루코코르티코이드 수용체 길항제 병용투여를 통한 치매 예방 및 치료용 조성물 |
KR102311224B1 (ko) | 2021-04-23 | 2021-10-13 | 주식회사 아리바이오 | Pde5 억제제와 글루코코르티코이드 수용체 길항제 병용투여를 통한 치매 예방 및 치료용 조성물 |
WO2023052407A1 (en) | 2021-09-29 | 2023-04-06 | Topadur Pharma Ag | Topical compositions of 2-phenyl-3,4-dihydropyrrolo[2,l-f] [1,2,4]triazinone derivatives and uses thereof |
WO2023166013A1 (en) | 2022-03-02 | 2023-09-07 | Topadur Pharma Ag | Topical compositions and uses therof |
KR20230129639A (ko) * | 2022-03-02 | 2023-09-11 | 연세대학교 산학협력단 | 이중작용 pde5 억제제/질산유기에스터의 국소 혈류 증진을 위한 경피 투약 형태 |
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JPS5761734B2 (es) * | 1973-09-27 | 1982-12-25 | Takeda Chemical Industries Ltd | |
JPS5761734A (en) * | 1980-10-02 | 1982-04-14 | Teijin Ltd | Spun like fabric |
GB9013750D0 (en) * | 1990-06-20 | 1990-08-08 | Pfizer Ltd | Therapeutic agents |
GB9301192D0 (en) * | 1993-06-09 | 1993-06-09 | Trott Francis W | Flower shaped mechanised table |
JP3713783B2 (ja) * | 1995-01-20 | 2005-11-09 | 大正製薬株式会社 | 1H−ピラゾロ[3,4−d]ピリミジン−4−オン誘導体 |
SK285991B6 (sk) * | 1997-04-25 | 2008-01-07 | Pfizer Inc. | Pyrazolopyrimidinóny, spôsob a medziprodukty na ich výrobu, ich použitie a farmaceutické a veterinárne kompozície na ich báze |
EA200000969A1 (ru) * | 1998-04-20 | 2001-06-25 | Пфайзер Инк. | ИНГИБИТОРЫ цГМБ ФДЭ5 НА ОСНОВЕ ПИРАЗОЛПИРИМИДИНОНА ДЛЯ ЛЕЧЕНИЯ ПОЛОВЫХ ДИСФУНКЦИЙ |
KR100358083B1 (ko) * | 2000-02-17 | 2002-10-25 | 에스케이케미칼주식회사 | 피롤로피리미디논 유도체와 이의 제조방법, 그리고 이의용도 |
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2000
- 2000-02-17 KR KR20000007625A patent/KR100358083B1/ko active IP Right Grant
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2001
- 2001-02-15 ES ES01908397T patent/ES2222344T3/es not_active Expired - Lifetime
- 2001-02-15 IL IL15123401A patent/IL151234A0/xx unknown
- 2001-02-15 US US10/204,327 patent/US6962911B2/en not_active Expired - Lifetime
- 2001-02-15 JP JP2001560209A patent/JP4845076B2/ja not_active Expired - Lifetime
- 2001-02-15 DE DE60103508T patent/DE60103508T2/de not_active Expired - Lifetime
- 2001-02-15 CN CNB018075002A patent/CN1312153C/zh not_active Expired - Lifetime
- 2001-02-15 AU AU2001236140A patent/AU2001236140B9/en not_active Expired
- 2001-02-15 EP EP01908397A patent/EP1257553B1/en not_active Expired - Lifetime
- 2001-02-15 MX MXPA02007942A patent/MXPA02007942A/es active IP Right Grant
- 2001-02-15 DK DK01908397T patent/DK1257553T3/da active
- 2001-02-15 WO PCT/KR2001/000227 patent/WO2001060825A1/en active IP Right Grant
- 2001-02-15 CA CA002400268A patent/CA2400268C/en not_active Expired - Lifetime
- 2001-02-15 RU RU2002124872/04A patent/RU2263676C2/ru active
- 2001-02-15 PT PT01908397T patent/PT1257553E/pt unknown
- 2001-02-15 NZ NZ520842A patent/NZ520842A/en not_active IP Right Cessation
- 2001-02-15 PL PL358188A patent/PL210796B1/pl unknown
- 2001-02-15 AU AU3614001A patent/AU3614001A/xx active Pending
- 2001-02-15 BR BRPI0108395A patent/BRPI0108395B8/pt not_active IP Right Cessation
- 2001-02-15 TR TR2004/02101T patent/TR200402101T4/xx unknown
- 2001-02-15 HU HU0300527A patent/HU230344B1/hu unknown
- 2001-02-15 AT AT01908397T patent/ATE267829T1/de active
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2002
- 2002-08-13 IL IL151234A patent/IL151234A/en active IP Right Grant
- 2002-08-13 NO NO20023823A patent/NO323553B1/no not_active IP Right Cessation
- 2002-08-16 ZA ZA200206587A patent/ZA200206587B/xx unknown
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