HRP20120667T2 - Derivat benzimidazola i njegova uporaba kao antagonista aii receptora - Google Patents
Derivat benzimidazola i njegova uporaba kao antagonista aii receptora Download PDFInfo
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- HRP20120667T2 HRP20120667T2 HRP20120667TT HRP20120667T HRP20120667T2 HR P20120667 T2 HRP20120667 T2 HR P20120667T2 HR P20120667T T HRP20120667T T HR P20120667TT HR P20120667 T HRP20120667 T HR P20120667T HR P20120667 T2 HRP20120667 T2 HR P20120667T2
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- 125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 title 1
- 239000002464 receptor antagonist Substances 0.000 title 1
- 229940044551 receptor antagonist Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 10
- 150000003839 salts Chemical class 0.000 claims 7
- 229940079593 drug Drugs 0.000 claims 6
- 239000003814 drug Substances 0.000 claims 6
- 230000032050 esterification Effects 0.000 claims 4
- 238000005886 esterification reaction Methods 0.000 claims 4
- YAPQBXQYLJRXSA-UHFFFAOYSA-N theobromine Chemical compound CN1C(=O)NC(=O)C2=C1N=CN2C YAPQBXQYLJRXSA-UHFFFAOYSA-N 0.000 claims 4
- -1 5-methyl-2-oxo-1,3-dioxol-4-yl Chemical group 0.000 claims 3
- 229940127291 Calcium channel antagonist Drugs 0.000 claims 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 3
- 125000000217 alkyl group Chemical group 0.000 claims 3
- 239000000480 calcium channel blocker Substances 0.000 claims 3
- 239000002934 diuretic Substances 0.000 claims 3
- 125000005843 halogen group Chemical group 0.000 claims 3
- 238000000034 method Methods 0.000 claims 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims 2
- JIVPVXMEBJLZRO-CQSZACIVSA-N 2-chloro-5-[(1r)-1-hydroxy-3-oxo-2h-isoindol-1-yl]benzenesulfonamide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC([C@@]2(O)C3=CC=CC=C3C(=O)N2)=C1 JIVPVXMEBJLZRO-CQSZACIVSA-N 0.000 claims 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims 2
- 150000008065 acid anhydrides Chemical class 0.000 claims 2
- 229960000528 amlodipine Drugs 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
- 229960001523 chlortalidone Drugs 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 claims 2
- 229960004559 theobromine Drugs 0.000 claims 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims 2
- NSVFSAJIGAJDMR-UHFFFAOYSA-N 2-[benzyl(phenyl)amino]ethyl 5-(5,5-dimethyl-2-oxido-1,3,2-dioxaphosphinan-2-yl)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylate Chemical compound CC=1NC(C)=C(C(=O)OCCN(CC=2C=CC=CC=2)C=2C=CC=CC=2)C(C=2C=C(C=CC=2)[N+]([O-])=O)C=1P1(=O)OCC(C)(C)CO1 NSVFSAJIGAJDMR-UHFFFAOYSA-N 0.000 claims 1
- BKYKPTRYDKTTJY-UHFFFAOYSA-N 6-chloro-3-(cyclopentylmethyl)-1,1-dioxo-3,4-dihydro-2H-1$l^{6},2,4-benzothiadiazine-7-sulfonamide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(S(N2)(=O)=O)=C1NC2CC1CCCC1 BKYKPTRYDKTTJY-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- JZUFKLXOESDKRF-UHFFFAOYSA-N Chlorothiazide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC2=C1NCNS2(=O)=O JZUFKLXOESDKRF-UHFFFAOYSA-N 0.000 claims 1
- VXLCNTLWWUDBSO-UHFFFAOYSA-N Ethiazide Chemical compound ClC1=C(S(N)(=O)=O)C=C2S(=O)(=O)NC(CC)NC2=C1 VXLCNTLWWUDBSO-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- KLDXJTOLSGUMSJ-JGWLITMVSA-N Isosorbide Chemical compound O[C@@H]1CO[C@@H]2[C@@H](O)CO[C@@H]21 KLDXJTOLSGUMSJ-JGWLITMVSA-N 0.000 claims 1
- CESYKOGBSMNBPD-UHFFFAOYSA-N Methyclothiazide Chemical compound ClC1=C(S(N)(=O)=O)C=C2S(=O)(=O)N(C)C(CCl)NC2=C1 CESYKOGBSMNBPD-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- UJEWTUDSLQGTOA-UHFFFAOYSA-N Piretanide Chemical compound C=1C=CC=CC=1OC=1C(S(=O)(=O)N)=CC(C(O)=O)=CC=1N1CCCC1 UJEWTUDSLQGTOA-UHFFFAOYSA-N 0.000 claims 1
- ABBQHOQBGMUPJH-UHFFFAOYSA-M Sodium salicylate Chemical compound [Na+].OC1=CC=CC=C1C([O-])=O ABBQHOQBGMUPJH-UHFFFAOYSA-M 0.000 claims 1
- FNYLWPVRPXGIIP-UHFFFAOYSA-N Triamterene Chemical compound NC1=NC2=NC(N)=NC(N)=C2N=C1C1=CC=CC=C1 FNYLWPVRPXGIIP-UHFFFAOYSA-N 0.000 claims 1
- 229960000571 acetazolamide Drugs 0.000 claims 1
- BZKPWHYZMXOIDC-UHFFFAOYSA-N acetazolamide Chemical compound CC(=O)NC1=NN=C(S(N)(=O)=O)S1 BZKPWHYZMXOIDC-UHFFFAOYSA-N 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 229940100198 alkylating agent Drugs 0.000 claims 1
- 239000002168 alkylating agent Substances 0.000 claims 1
- QJFSABGVXDWMIW-UHFFFAOYSA-N azilsartan medoxomil Chemical compound C=12N(CC=3C=CC(=CC=3)C=3C(=CC=CC=3)C=3NC(=O)ON=3)C(OCC)=NC2=CC=CC=1C(=O)OCC=1OC(=O)OC=1C QJFSABGVXDWMIW-UHFFFAOYSA-N 0.000 claims 1
- IIOPLILENRZKRV-UHFFFAOYSA-N azosemide Chemical compound C=1C=CSC=1CNC=1C=C(Cl)C(S(=O)(=O)N)=CC=1C1=NN=N[N]1 IIOPLILENRZKRV-UHFFFAOYSA-N 0.000 claims 1
- 229960004988 azosemide Drugs 0.000 claims 1
- 229950007003 benzylhydrochlorothiazide Drugs 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 1
- 229960004064 bumetanide Drugs 0.000 claims 1
- 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 1
- AVVIDTZRJBSXML-UHFFFAOYSA-L calcium;2-carboxyphenolate;dihydrate Chemical compound O.O.[Ca+2].OC1=CC=CC=C1C([O-])=O.OC1=CC=CC=C1C([O-])=O AVVIDTZRJBSXML-UHFFFAOYSA-L 0.000 claims 1
- 239000003054 catalyst Substances 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 229960003206 cyclopenthiazide Drugs 0.000 claims 1
- 229950003102 efonidipine Drugs 0.000 claims 1
- AVOLMBLBETYQHX-UHFFFAOYSA-N etacrynic acid Chemical compound CCC(=C)C(=O)C1=CC=C(OCC(O)=O)C(Cl)=C1Cl AVOLMBLBETYQHX-UHFFFAOYSA-N 0.000 claims 1
- 229960003199 etacrynic acid Drugs 0.000 claims 1
- 229960003883 furosemide Drugs 0.000 claims 1
- 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 1
- 229960002003 hydrochlorothiazide Drugs 0.000 claims 1
- 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 1
- 229960003313 hydroflumethiazide Drugs 0.000 claims 1
- 229960004569 indapamide Drugs 0.000 claims 1
- 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 1
- 229960002479 isosorbide Drugs 0.000 claims 1
- 229960003963 manidipine Drugs 0.000 claims 1
- ANEBWFXPVPTEET-UHFFFAOYSA-N manidipine Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OCCN2CCN(CC2)C(C=2C=CC=CC=2)C=2C=CC=CC=2)C1C1=CC=CC([N+]([O-])=O)=C1 ANEBWFXPVPTEET-UHFFFAOYSA-N 0.000 claims 1
- 229960003739 methyclothiazide Drugs 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 229960001783 nicardipine Drugs 0.000 claims 1
- 229960001597 nifedipine Drugs 0.000 claims 1
- 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 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 229960001085 piretanide Drugs 0.000 claims 1
- 239000011591 potassium Substances 0.000 claims 1
- 229910052700 potassium Inorganic materials 0.000 claims 1
- 229960004025 sodium salicylate Drugs 0.000 claims 1
- LXMSZDCAJNLERA-ZHYRCANASA-N spironolactone Chemical compound C([C@@H]1[C@]2(C)CC[C@@H]3[C@@]4(C)CCC(=O)C=C4C[C@H]([C@@H]13)SC(=O)C)C[C@@]21CCC(=O)O1 LXMSZDCAJNLERA-ZHYRCANASA-N 0.000 claims 1
- 229960002256 spironolactone Drugs 0.000 claims 1
- 239000003451 thiazide diuretic agent Substances 0.000 claims 1
- 229960001288 triamterene Drugs 0.000 claims 1
- 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 1
- 229960004813 trichlormethiazide Drugs 0.000 claims 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4164—1,3-Diazoles
- A61K31/4184—1,3-Diazoles condensed with carbocyclic rings, e.g. benzimidazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4245—Oxadiazoles
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- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
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Claims (9)
1. Postupak proizvodnje spoja formule (I):
[image]
gdje je R1 skupina predstavljena formulom:
[image]
pri čemu su R2, R3, R4, R5, R6, R7 i R8 svaki neovisno atom vodika ili C1-6 alkil, ili njegove soli, naznačen time, da obuhvaća sljedeće korake:
(1) reagiranje spoja formule (II):
[image]
ili njegove soli, sa sredstvom acilacije (III):
[image]
gdje X je atom halogena i R12 je alkil, alkoksi ili fenil opcijski supstituiran s atomom halogena, C1-6alkilom ili nitro skupinom, u prisutnosti baze za stvaranje smjese kiselog anhidrida te reagiranje smjese kiselog anhidrida s alkoholom (IV):
HO-R1 (IV)
gdje je R1 određen gore, u prisutnosti baze da se omogući esterifikacija,
(2) reagiranje spoja formule (II):
[image]
ili njegove soli, s tionil kloridom ili oksalil kloridom u prisutnosti katalizatora za stvaranje kiselog klorida i reagiranje kiselog klorida s alkoholom (IV):
HO-R1 (IV)
gdje je R1 određen gore, u prisutnosti baze da se omogući esterifikacija,
(3) reagiranje spoja formule (II):
[image]
ili njegove soli, sa sredstvom za alkilaciju (V):
X'-R1(V)
gdje X' je atom halogena i R1 je određen gore, ako je potrebno u prisutnosti baze da se omogući esterifikacija, ili
(4) reagiranje spoja formule (II):
[image]
ili njegove soli, s alkoholom (IV):
HO-R1 (IV)
gdje R1 je određen gore, u prisutnosti kondenzatora da se omogući esterifikacija.
2. Postupak prema zahtjevu 1, naznačen time, da R1 je skupina predstavljena formulom:
[image]
gdje R1 je određen u zahtjevu 1.
3. Postupak prema zahtjevu 1, naznačen time, da spoj je 5-metil-2-okso-1,3-dioksol-4-il)metil-2-etoksi-1-{[2'-(5-okso-4,5-dihidro-1,2,4-oksadiazol-3-il)bifenil-4-il]metil}-1H-benzimidazol-7-karboksilat-kalijevasol.
4. Lijek, naznačen time, da sadrži spoj formule (I):
[image]
gdje R1 je skupina predstavljena formulom:
[image]
pri čemu su R2, R3, R4, R5, R6, R7 i R8 svaki neovisno atom vodika ili C1-6 alkil, ili njegovu sol u kombinaciji s diuretičkim sredstvom, pri čemu je diuretičko sredstvo odabrano od sljedećih: teobromin i natrij salicilat, teobromin i kalcij salicilat, etiazid, ciklopentiazid, triklormetiazid, hidroklorotiazid, hidroflumetiazid, benzil hidroklorotiazid, penflutiazid, poli-5-tiazid, metiklotiazid, spironolakton, triamteren, acetazolamid, klortalidon, mefruzid, indapamid, azosemid, izosorbid, etakrinska kiselina, piretanid, bumetanid i furosemid.
5. Lijek prema zahtjevu 4, naznačen time, da diuretičko sredstvo je klortalidon.
6. Lijek, naznačen time, da sadrži spoj formule (I):
[image]
gdje R1 je skupina predstavljena formulom:
[image]
pri čemu su R2, R3, R4, R5, R6, R7 i R8 svaki neovisno atom vodika ili C1-6alkil, ili njegovu sol u kombinaciji s antagonistom kalcija, gdje je antagonist kalcija odabran od sljedećih: manidipin, nifedipin, amlodipin, efonidipin i nikardipin.
7. Lijek prema zahtjevu 6, naznačen time, da antagonist kalcija je amlodipin.
8. Lijek prema bilo kojem od zahtjeva 4 do 7, naznačen time, da spoj formule (I) je (5-metil-2-okso-1,3-dioksol-4-il)metil-2-etoksi-1-{[2'-(5-okso-4,5-dihidro-1,2,4-oksadiazol-3-il)bifenil-4-il]metil}-1H-benzimidazol-7-karboksilat.
9. Lijek prema bilo kojem od zahtjeva 4 do 7, naznačen time, da spoj formule (I) je (5-metil-2-okso-1,3 -dioksol-4-il)metil-2-etoksi-1-{[2'-(5-okso-4,5-dihidro-1,2,4-oksadiazol-3-il)bifenil-4-il]metil}-1H-benzimidazol-7-karboksilat-kalcijevasol.
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