SI20818B - N-heterocikliäśni derivati kot nos inhibitorji - Google Patents
N-heterocikliäśni derivati kot nos inhibitorji Download PDFInfo
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- SI20818B SI20818B SI200020040A SI200020040A SI20818B SI 20818 B SI20818 B SI 20818B SI 200020040 A SI200020040 A SI 200020040A SI 200020040 A SI200020040 A SI 200020040A SI 20818 B SI20818 B SI 20818B
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- Slovenia
- Prior art keywords
- amino
- methylpyrimidin
- imidazol
- acetamide
- alkyl
- Prior art date
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- 239000003112 inhibitor Substances 0.000 title claims abstract 4
- 150000001875 compounds Chemical class 0.000 claims abstract 14
- 238000000034 method Methods 0.000 claims abstract 8
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 40
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims 35
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 28
- -1 - (CH 2) n N (R 1) 2 Chemical group 0.000 claims 27
- 125000000217 alkyl group Chemical group 0.000 claims 22
- 125000003118 aryl group Chemical group 0.000 claims 16
- 229910052739 hydrogen Inorganic materials 0.000 claims 13
- 239000001257 hydrogen Substances 0.000 claims 13
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 12
- 125000000623 heterocyclic group Chemical group 0.000 claims 11
- 150000002431 hydrogen Chemical class 0.000 claims 11
- 125000001475 halogen functional group Chemical group 0.000 claims 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 5
- HBEDSQVIWPRPAY-UHFFFAOYSA-N 2,3-dihydrobenzofuran Chemical compound C1=CC=C2OCCC2=C1 HBEDSQVIWPRPAY-UHFFFAOYSA-N 0.000 claims 4
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 claims 4
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims 4
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 4
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 4
- 125000006626 methoxycarbonylamino group Chemical group 0.000 claims 4
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 claims 4
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 3
- 125000003545 alkoxy group Chemical group 0.000 claims 3
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims 3
- 125000001188 haloalkyl group Chemical group 0.000 claims 3
- 239000000203 mixture Substances 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- 206010007559 Cardiac failure congestive Diseases 0.000 claims 2
- 206010056370 Congestive cardiomyopathy Diseases 0.000 claims 2
- 201000010046 Dilated cardiomyopathy Diseases 0.000 claims 2
- 206010019280 Heart failures Diseases 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 230000005856 abnormality Effects 0.000 claims 2
- 201000006417 multiple sclerosis Diseases 0.000 claims 2
- AJFDBNQQDYLMJN-UHFFFAOYSA-N n,n-diethylacetamide Chemical compound CCN(CC)C(C)=O AJFDBNQQDYLMJN-UHFFFAOYSA-N 0.000 claims 2
- 210000000056 organ Anatomy 0.000 claims 2
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 1
- HIEWOWAWIPSVMZ-UHFFFAOYSA-N 2-[3-(2,3-dihydro-1,4-benzodioxin-6-ylmethylamino)propyl-(2-imidazol-1-yl-6-methylpyrimidin-4-yl)amino]-n-methylacetamide Chemical compound C=1C=C2OCCOC2=CC=1CNCCCN(CC(=O)NC)C(N=1)=CC(C)=NC=1N1C=CN=C1 HIEWOWAWIPSVMZ-UHFFFAOYSA-N 0.000 claims 1
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims 1
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 claims 1
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- 201000001320 Atherosclerosis Diseases 0.000 claims 1
- 201000006474 Brain Ischemia Diseases 0.000 claims 1
- 206010008120 Cerebral ischaemia Diseases 0.000 claims 1
- 206010009900 Colitis ulcerative Diseases 0.000 claims 1
- 208000011231 Crohn disease Diseases 0.000 claims 1
- 206010012289 Dementia Diseases 0.000 claims 1
- 208000007342 Diabetic Nephropathies Diseases 0.000 claims 1
- 208000032131 Diabetic Neuropathies Diseases 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 1
- 208000009329 Graft vs Host Disease Diseases 0.000 claims 1
- 208000001953 Hypotension Diseases 0.000 claims 1
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims 1
- 201000009906 Meningitis Diseases 0.000 claims 1
- 208000018737 Parkinson disease Diseases 0.000 claims 1
- 208000031481 Pathologic Constriction Diseases 0.000 claims 1
- 206010035664 Pneumonia Diseases 0.000 claims 1
- 208000013616 Respiratory Distress Syndrome Diseases 0.000 claims 1
- 206010040070 Septic Shock Diseases 0.000 claims 1
- 206010049771 Shock haemorrhagic Diseases 0.000 claims 1
- 208000000453 Skin Neoplasms Diseases 0.000 claims 1
- 208000006011 Stroke Diseases 0.000 claims 1
- 206010052779 Transplant rejections Diseases 0.000 claims 1
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims 1
- 201000006704 Ulcerative Colitis Diseases 0.000 claims 1
- 230000001154 acute effect Effects 0.000 claims 1
- 208000011341 adult acute respiratory distress syndrome Diseases 0.000 claims 1
- 201000000028 adult respiratory distress syndrome Diseases 0.000 claims 1
- 208000006673 asthma Diseases 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 206010008118 cerebral infarction Diseases 0.000 claims 1
- 230000001684 chronic effect Effects 0.000 claims 1
- 208000033679 diabetic kidney disease Diseases 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 208000024908 graft versus host disease Diseases 0.000 claims 1
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 1
- 230000036543 hypotension Effects 0.000 claims 1
- 239000007943 implant Substances 0.000 claims 1
- 208000014674 injury Diseases 0.000 claims 1
- 231100000516 lung damage Toxicity 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 1
- 239000002245 particle Substances 0.000 claims 1
- 244000052769 pathogen Species 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 208000037803 restenosis Diseases 0.000 claims 1
- 230000036303 septic shock Effects 0.000 claims 1
- 201000000849 skin cancer Diseases 0.000 claims 1
- 208000017520 skin disease Diseases 0.000 claims 1
- 230000000391 smoking effect Effects 0.000 claims 1
- 230000036262 stenosis Effects 0.000 claims 1
- 208000037804 stenosis Diseases 0.000 claims 1
- 201000000596 systemic lupus erythematosus Diseases 0.000 claims 1
- 230000008733 trauma Effects 0.000 claims 1
- 208000035408 type 1 diabetes mellitus 1 Diseases 0.000 claims 1
- 102000008299 Nitric Oxide Synthase Human genes 0.000 abstract 2
- 108010021487 Nitric Oxide Synthase Proteins 0.000 abstract 2
- 230000002194 synthesizing effect Effects 0.000 abstract 1
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- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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Abstract
Tukaj so opisani N-heterociklični derivati s formulo (Ya) pa tudi drugi N-heterocikli kot inhibitorji sintaze dušikovega oksida. V tem opisu so opisani tudi farmacevtski pripravki, ki vsebujejo te spojine, postopki za uporabo teh spojin kot inhibitorjev sintaze dušikovega oksida in postopki za sintetiziranje teh spojin.
Claims (13)
- -1- Sl20818 A/-HETEROCIKLIČNI DERIVATI KOT NOS INHIBITORJI Patentni zahtevki 1. Spojina s formulo (Ya), formulo (Yb) ali formulo (Yc): R4-(GH2), ^-(CH2)n'A N(Ya); R4-(CH2)m. /(CH2)n-A 7IT\ v ν' V N (Yb); N Ra R4-(CH2)m ^(GH2)n-A N N (Yc); Rs N nA\ N v kateri: n in m sta neodvisno celo število od 1 do 4; A je -C(0)0R1 ali -C(0)N(R1)R2; -2- vsak W je N ali CH; vsak R1 je neodvisno vodik, Ci-C8 alkil, aril ali aril Ci-C8 alkil; vsak R2 je neodvisno vodik, CrC20 alkil, -(CH2)n-N(R1)2, heterocikloalkil Ci-C8 alkil (po izbiri substituiran s Ci-C8 alkilom, halojem, Ci-C8 haloalkilom ali C-i-C8 alkoksijem), aril-Ci-C8 alkil (po izbiri substituiran s halojem, Ci-Ca alkilom, CrCe alkoksijem ali -N(R1)2); kadar je m celo število od 2 do 4, je lahko R1 2 ciano, heterociklil, hidroksi, -N(R1)R2, -N(R1)-C(0)-R1, -N(R1)-C(0)0R1, N(R1)-S(0),-R1 ali -N(R1)-C(0)-N(R1)2; kadar je m 1, je lahko R2 ciano ali heterociklil; R3 je vodik, halo, Ci-C8 alkil, aril, aril Ci-C8 alkil ali CrC8 haloalkil; t je celo število od 0 do 2; pri čemer se aril nanaša na fenilni ali naftilni radikal; kot enostavni stereoizomer ali njegova mešanica ali njegova farmacevtsko sprejemljiva sol.
- 2. Spojina po zahtevku 1 s formulo (Yc), v kateri: nje 1; m je 2 ali 3; A je -C(0)0R1 ali -C(0)N(R1)R2; vsak W je CH; R1 je vodik ali C-i-C8 alkil; in R2 je vodik, CrC20-alkil, -(CH2)n-N(R1)2, po izbiri substituirani heterociklil CrC8 alkil ali po izbiri substituiran aril-Ci-C8 alkil. 1 Spojina s formulo 3, v kateri je R2 -N(R1)R2, kjer je R1 vodik ali CrC8 alkil in R2 je heterociklil Ci-C8 alkil, ki ga izberemo iz skupine, ki jo sestavljata (1,3-benzodioksol-5-il)metil ali (1,4-benzodioksan-6-il)metil. 2 Spojina po zahtevku 4, izbrana iz skupine, ki jo sestavljajo: 3 2-[[3-[[(1,3-benzodioksol-5-il)metil](metil)amino]propil][2-(1 /-/-imidazol-1 -il)-6-metilpirimidin-4-il]amino]ocetna kislina, etil ester; 2-[[3-[[(1,3-benzodioksol-5-il)metil](metil)amino]propil][2-(1W-imidazol-1-il)-6- metilpirimidin-4-il]amino]-/\/,/N/-dietilacetamid; -3- 2-[[3-[[(1,3-benzodioksol-5-il)metil](metil)amino]propil][2-(1 H-imidazol-1-il)-6-metilpirimidin-4-il]amino]-A/-(2-dimetilaminoetil)acetamid; 2-[[3-[[(1,3-benzodioksol-5-il)metil](metil)amino]propil][2-(1 H-imidazol-1 -il)-6-metilpirimidin-4-il]amino]acetamid; 2-[[3-[(1,3-benzodioksol-5-il)metil]aminopropil][2-(1 H-imidazol-1 -il)-6-metilpirimidin-4-il]amino]-A/,A/-dietilacetamid; 2-[[3-[(1,3-benzodioksol-5-il)metil]aminopropil][2-(1 /-/-imidazol-1 -il)-6-metilpirimidin-4-il]amino]-/S/-metilacetamid; 2-[[3-[(1,4-benzodioksan-6-il)metil]aminopropil][2-(1 H-imidazol-1 -il)-6-metilpirimidin-4-li]amino]-A/-metilacetamid; 2-[[3-[(1,4-benzodioksan-6-il)metil]aminopropil][2-(1 H-imidazol-1-il)-6-metilpirimidin-4-il]amino]-/\/,A/-dietilacetamid; 2-[[3-[(1,4-benzodioksan-6-il)metil]aminopropil][2-(1 H-imidazol-1 -il)-6-metilpirimidin-4-il]amino]acetamid; in 2-[[3-[(1,3-benzodioksol-5-il)metil]aminopropil][2-(1 H-imidazol-1-il)-6-metilpirimidin-4-il]amino]acetamid.
- 5.Spojina po zahtevku 4, ki je: 2-[[3-[[(1,3-benzodioksol-5-il)metil](metil)amino]propil][2-(1 H-imidazol-1 -il)-6-metilpirimidin-4-il]amino]acetamid.
- 6. Spojina po zahtevku 2, v kateri je R4 heterociklil.
- 7. Spojina po zahtevku 6, izbrana iz skupine, ki jo sestavljajo: 2-[[piridin-3-ilmetil][2-(1 H-imidazol-1 -il)-6-metilpirimidin-4-il]amino]-A/-[2-(1,3-benzodioksol-5-il)etil]acetamid; 2-[[2-(1 H-imidazol-1 -il)-6-metilpirimidin-4-il][(1,3-benzodioksol-5-il)metil]amino]-A/-[2-(1,3-benzodioksol-5-il)etil]acetamid; in 2-[[2-(1 H-imidazol-1 -il)-6-metilpirimidin-4-il][2-(morfolin-4-il)etil]amino]-A/-[2-(1,3-benzodioksol-5-il)etil]acetamid. -4-
- 8. Spojina po zahtevku 2, v kateri je R4 hidroksi, ciano, -N(R1)R2, -N(R1)-C(0)-R1, -N(R1)-C(0)0R1, -N(R1)-S(0),-R1 ali -N(R1)-C(0)-N(R1)2, kjer sta vsak R1 in vsak R2 neodvisno vodik, C-i-Ce alkil ali aril Ci-Cs alkil.
- 9. Spojina po zahtevku 8, izbrana iz skupine, ki jo sestavljajo: 2-[[3-hidroksipropil][2-(1 H-imidazol-1-il)-6-metilpirimidin-4-il]amino]-A/-[2-(1,3-benzodioksol-5-il)etil]acetamid; 2-[[2-cianoetil][2-(1 H-imidazol-1 -il)-6-metilpirimidin-4-il]amino]-A/-[2-(1,3-benzodioksol-5-il)etil]acetamid; 2-[[3-(dimetilamino)propil][2-(1 H-imidazol-1-il)-6-metilpirimidin-4-il]amino]-A/-[2-(1,3-benzodioksol-5-il)etil]acetamid; 2-[[3-(acetilamino)propil][2-(1 H- imidazol-1 -il)-6-metilpirimidin-4-il]amino]-/\/-[2-(1,3-benzodioksol-5-il)etil]acetamid; 2-[[3-(metilsulfonilamino)propil][2-(1/-/-imidazol-1-il)-6-metilpirimidin-4-il]amino]-A/-[2- (1,3benzodioksol-5-il)etil]acetamid; 2-[[3-(metoksikarbonilamino)propil][2-(1H-imidazol-1-il)-6-metilpirimidin-4-il]amino]-N- [2(1,3-benzodioksol-5-il)etil]acetamid; 2-[[3-(fenilmetilamino)propil][2-(1 H-imidazol-1 -ii)-6-metilpirimidin-4-il]amino]-A/-[2-(1,3--benzodioksol-5-il)etil]acetamid; 2-[[3-aminopropil][2-(1 H-imidazol-1 -il)-6-metilpirimidin-4-il]amino]-A/-[2-(1,3-benzodioksol-5-il )etil]acetamid; 2-[[3-aminopropil][2-(1 H-imidazol-1-il)-6-metilpirimidin-4-il]amino]-A/-[2-(4-metoksifenil)etil]acetamid; 2-[[3-(metilsulfonilamino)propil][2-(1H-imidazol-1-il)-6-metilpirimidin-4-il]amino]-/\/-[2-(4- metoksifenil)etil]acetamid; 2-[[3-(metoksikarbonilamino)propil][2-(1H-imidazol-1-il)-6-metilpirimidin-4-il]amino]-/V- [2-(4metoksifenil)etil]acetamid; -5- 2-[[3-(fenilmetilamino)propil][2-(1/-/-imidazol-1-il)-6-metilpirimidin-4-il]amino]-/\/-[2-(4-metoksifenil)etil]acetamid; 2-[[3-(acetilamino)propil][2-(1/-/-imidazol-1-il)-6-metilpirimidin-4-il]amino]-/\/-[2-(4- metoksifenil)etil]acetamid; 2-[[3-aminopropil][2-(1 H- imidazol-1 -il)-6-metilpirimidin-4-il]amino]-A/-[2-(1,4-benzodioksan-6-il)etil]acetamid; 2-[[3-(metoksikarbonilamino)propil][2-(1H-imidazol-1-il)-6-metilpirimidin-4-il]amino]-A/- [2(1,4-benzodioksan-6-il)etil]acetamid; 2-[[3-(di(fenilmetil)amino)propil][2-(1H-imidazol-1-il)-6-metilpirimidin-4-il]amino]-/V-[2- (1,4-benzodioksan-6-il)etil]acetamid; 2-[[3-(acetilamino)propil][2-(1 H-imidazol-1 -il)-6-metilpirimidin-4-il]amino]-/V-[2-(1,4-benzodioksan-6-il)etil]acetamid; 2-[[3-(metilsulfonilamino)propil][2-(1H-imidazol-1-il)-6-metiipirimidin-4-il]amino)-/\/-[2- (1,4-benzodioksan-6-il)etil]acetamid; 2-[[3-(dimetilamino)propil][2-(1 H-imidazol-1 -il)-6-metilpirimidin-4-il]amino]-A/-[2-(1,4-benzodioksan-6-il)etil]acetamid; 2-[[3-(dimetilamino)propil][2-(1H-imidazol-1-il)-6-metilpirimidin-4-il]amino]-A/-[2-(4- metoksifenil)etil]acetamid; 2-[[3-(ureido)propil][2-(1/-/-imidazol-1-il)-6-metilpirimidin-4-il]amino]-A/-[2-(4- metoksifenil)etil]acetamid; 2-[[3-(fenilmetilamino)propil][2-(1 H- imidazol-1 -il)-6-metilpirimidin-4-ii]amino]-A/-[2-(1,4-benzodioksan-6-il)etil]acetamid; 2-[[3-(fenilmetilamino)propil][2-(1/-/-imidazol-1-il)-6-metilpirimidin-4-il]amino]-A/-[2-(2,3-dihidrobenzofuran-5-il)etil]acetamid; 2-[[3-aminopropil][2-(1 H-imidazol-1-il)-6-metilpirimidin-4-il]amino]-A/-[2-(2,3-dihidrobenzofuran-5-il)etil]acetamid; 2-[[3-(dimetilamino)propil][2-(1H-imidazol-1-il)-6-metilpirimidin-4-il]amino]-A/-[2-(2,3- dihidrobenzofuran-5-il)etil]acetamid; 2-[[3-(acetilamino)propil][2-(1 /-/-imidazol-1 -il)-6-metilpirimidin-4-il]amino]-A/-[2-(2,3-dihidrobenzofuran-5-il)etil]acetamid; -6- 2-[[3-(metoksikarbonilamino)propil][2-(1H-imidazol-1-il)-6-metilpirimidin-4-il]amino]-/\/- [2(2,3-dihidrobenzofuran-5-il)etil]acetamid; 2-[[3-(metilsulfonilamino)propil][2-(1/-/-imidazol-1-il)-6-metilpirimidin-4-iljamino]-A/-[2- (2,3-dihidrobenzofuran-5-il)etil]acetamid; 2-[[3-(ureido)propil][2-(1 H-imidazol-1 -il)-6-metilpirimidin-4-il)amino]-A/-[2-(1,4-benzodioksan-6-il)etil)acetamid; in 2-[[3-(ureido)propil][2-(1H-imidazol-1-il)-6-metilpirimidin-4-il]amino]-/\/-[2-(2I3- dihidrobenzofuran-5-il)etil]acetamid.
- 10. Farmacevtski pripravek, ki vsebuje spojino s formulo (Ya), formulo (Yb) ali formulo (Yc): -7- ^-(CH^ /-(CH2)n-A N N N (Ya); R5 \ / R4-(CH2)m .(CH2)n-A NR4-(CH2)m. .(GH2)„'A Nv kateri: n in m sta neodvisno celo število od 1 do 4; A je -C(0)0R1 ali -C(0)N(R1)R2; vsak W je N ali CH; vsak R1 je neodvisno vodik, C-i-C8 alkil, aril ali aril-Ci-C8 alkil; vsak R2 je neodvisno vodik, CrC2o alkil, -(CH2)n-N(R1)2, heterociklil CrC8 alkil (po izbiri substituiran s Ci-C8 alkilom, halojem, CrC8 haloalkilom ali Ci-C8 alkoksijem), aril-Cr C8 alkil (po izbiri substituiran s halojem, C-i-C8 alkilom, Ci-C8 alkoksijem ali -N(R1)2); kadar je m celo število od 2 do 4, je lahko R4 ciano, heterociklil, hidroksi, -N(R1)R2, -N(R1)-C(0)-R\ -N(R1)-C(0)0R1, N(R1)-S(0)rR1 ali -N(R1)-C(0)-N(R1)2; kadar je m 1, je lahko R4 ciano ali heterociklil; R5 je vodik, halo, Ci-C8 alkil, aril, aril CrC8 alkil ali Ci-Ce haloalkil; -8- t je celo število od 0 do 2; pri čemer se aril nanaša na fenilni ali naftilni radikal; kot enostavni stereoizomer ali njegova mešanica ali njegova farmacevtsko sprejemljiva sol in njegov farmacevtsko sprejemljiv ekscipient.
- 11. Postopek za izdelavo zdravila za zdravljenje stanja, ki je rezultat abnormalnosti v nastajanju dušikovega oksida, ki obsega dajanje terapevtsko učinkovite količine spojine s formulo (Ya), formulo (Yb) ali formulo (Yc): NNNv kateri: n in m sta neodvisno celo število od 1 do 4; -9- A je -C(0)0R1 ali -C(0)N(R1)R2; vsak W je N ali CH; vsak R1 je neodvisno vodik, Ci-Ce alkil, aril ali aril Ci-Ce alkil; vsak R2 je neodvisno vodik, C1-C20 alkil, -(CH2)n-N(R1)2, heterociklil Ci-Cs alkil (po izbiri substituiran s CrCe alkilom, halojem, CrCe haloalkilom ali CrCe alkoksijem), aril Ci-Ce alkil (po izbiri substituiran s halojem, CrCe alkilom, CrCe alkoksijem ali -N(R1)2); kadar je m celo število od 2 do 4, je lahko R4 ciano, heterociklil, hidroksi, -N(R1)R2, -N(R1)-C(0)-R\ -N(R1)-C(0)0R\ N(R1)-S(0)t-R1 ali -N(R1)-C(0)-N(R1)2; kadar je m 1, je lahko R4 ciano ali heterociklil; R5 je vodik, halo, CrCe alkil, aril, aril CrCe alkil ali CrCe haloalkil; t je celo število od 0 do 2; pri čemer se aril nanaša na fenilni ali naftilni radikal; kot enostavni stereoizomer ali njegova mešanica ali njegova farmacevtsko sprejemljiva sol.
- 12. Postopek po zahtevku 11, pri čemer je stanje, ki je rezultat abnormalnosti v nastajanju dušikovega oksida, izbrano iz skupine, ki jo sestavljajo multipla skleroza, kap ali cerebralna ishemija, Alzheimerjeva bolezen, demenca HIV, Parkinsonova bolezen, meningitis, dilatirana kardiomiopatija in kongestivno srčno popuščanje, ateroskleroza, restenoza ali stenoza vsadka, septični šok ali hipotenzija, hemoragični šok, astma, sindrom dihalne stiske pri odraslem, poškodba pljuč zaradi kajenja ali delcev, pljučnice povzročene s patogenimi organizmi, travme različnih etiologij, revmatoidni artritis in osteoartritis, glomerulonefritis, sistemski lupus eritematosus, vnetne bolezni črevesja, kot so ulcerozni kolitis in Crohnova bolezen, inzulinsko-odvisni diabetes melitus, diabetična nevropatija ali nefropatija, akutno ali kronično zavračanje presajenega organa, vaskulopatije presajenega organa, bolezen presadek-proti-gostiteIj, psoriaza in druge vnetne kožne bolezni ter rak.
- 13. Postopek po zahtevku 12, kjer je stanje multipla skleroza.
- 14. Postopek po zahtevku 12, kjer je stanje revmatoidni artritis.
- 15. Postopek po zahtevku 12, kjer je stanje dilatirana kardiomiopatija. -ΙΟ Ι 6. Postopek po zahtevku 12, kjer je stanje kongestivno srčno popuščanje.
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| US09/383,813 US6432947B1 (en) | 1997-02-19 | 1999-08-26 | N-heterocyclic derivatives as NOS inhibitors |
| PCT/US2000/023173 WO2001014371A1 (en) | 1999-08-26 | 2000-08-24 | N-heterocyclic derivatives as nos inhibitors |
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| WO2019183577A1 (en) | 2018-03-23 | 2019-09-26 | Carmot Therapeutics, Inc. | Modulators of g-protein coupled receptors |
| EP3628669A1 (en) | 2018-09-28 | 2020-04-01 | GenKyoTex Suisse SA | Novel compounds as nadph oxidase inhibitors |
| IL308392A (en) | 2021-05-13 | 2024-01-01 | Carmot Therapeutics Inc | G protein-coupled receptor modulators |
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| JPS6339875A (ja) | 1986-08-05 | 1988-02-20 | Nissin Food Prod Co Ltd | ピリミジン誘導体 |
| DE4118720A1 (de) | 1991-06-07 | 1992-12-10 | Bayer Ag | Substituierte imidazolinylpyrimidine |
| EP0548553A1 (en) * | 1991-11-25 | 1993-06-30 | Takeda Chemical Industries, Ltd. | Optically active azole compounds, their production and use |
| CA2131004A1 (en) * | 1992-02-28 | 1993-09-02 | Hideshi Kobayashi | S-triazine derivative and remedy for estrogen-dependent disease containing said derivative as effective component |
| TW279864B (sl) * | 1993-02-19 | 1996-07-01 | Janssen Pharmaceutica Nv | |
| US5593992A (en) | 1993-07-16 | 1997-01-14 | Smithkline Beecham Corporation | Compounds |
| EP0640599B1 (en) | 1993-08-26 | 1998-03-04 | Ono Pharmaceutical Co., Ltd. | 4-Aminopyrimidine derivatives |
| US5426110A (en) | 1993-10-06 | 1995-06-20 | Eli Lilly And Company | Pyrimidinyl-glutamic acid derivatives |
| US5629322A (en) | 1994-11-15 | 1997-05-13 | Merck & Co., Inc. | Cyclic amidine analogs as inhibitors of nitric oxide synthase |
| WO1996014842A1 (en) | 1994-11-15 | 1996-05-23 | Merck & Co., Inc. | Substituted heterocycles as inhibitors of nitric oxide synthase |
| BR9611157A (pt) * | 1995-11-01 | 1999-03-30 | Novartis Ag | Derivados de purina e processos para sua preparação |
| ZA977427B (en) | 1996-09-04 | 1998-03-02 | Dainippon Pharmaceutical Co | 2,4-disubstituted pyrimidine derivative, process for preparing the same, and a pharmaceutical composition containing the same. |
| PL335235A1 (en) * | 1997-02-19 | 2000-04-10 | Berlex Lab | N-heterocyclic derivatives as nos inhibitors |
| US6432947B1 (en) * | 1997-02-19 | 2002-08-13 | Berlex Laboratories, Inc. | N-heterocyclic derivatives as NOS inhibitors |
| US6172005B1 (en) * | 1997-03-11 | 2001-01-09 | E. I. Du Pont De Nemours And Company | Heteroaryl azole herbicides |
| US6525051B2 (en) | 2000-03-27 | 2003-02-25 | Schering Aktiengesellschaft | N-heterocyclic derivatives as NOS inhibitors |
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Effective date: 20090218 |
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