ME00381B - Tri-peptidi kao inhibitori hepatitisa c - Google Patents
Tri-peptidi kao inhibitori hepatitisa cInfo
- Publication number
- ME00381B ME00381B MEP-2008-585A MEP58508A ME00381B ME 00381 B ME00381 B ME 00381B ME P58508 A MEP58508 A ME P58508A ME 00381 B ME00381 B ME 00381B
- Authority
- ME
- Montenegro
- Prior art keywords
- alkyl
- group
- substituted
- amino
- optionally substituted
- Prior art date
Links
- 239000003112 inhibitor Substances 0.000 title claims 2
- 208000006454 hepatitis Diseases 0.000 title 1
- 231100000283 hepatitis Toxicity 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims abstract 182
- 125000003368 amide group Chemical group 0.000 claims abstract 92
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract 88
- 150000001875 compounds Chemical class 0.000 claims abstract 79
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract 57
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract 55
- 150000001408 amides Chemical class 0.000 claims abstract 54
- 125000003118 aryl group Chemical group 0.000 claims abstract 54
- 150000002148 esters Chemical class 0.000 claims abstract 53
- 150000003839 salts Chemical class 0.000 claims abstract 53
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract 50
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 47
- 125000002252 acyl group Chemical group 0.000 claims abstract 31
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims abstract 30
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims abstract 24
- 229910052736 halogen Inorganic materials 0.000 claims abstract 21
- 125000005843 halogen group Chemical group 0.000 claims abstract 19
- 150000002367 halogens Chemical group 0.000 claims abstract 15
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims abstract 14
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims abstract 11
- 125000004001 thioalkyl group Chemical group 0.000 claims abstract 10
- 125000001188 haloalkyl group Chemical group 0.000 claims abstract 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract 8
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract 8
- 125000004966 cyanoalkyl group Chemical group 0.000 claims abstract 7
- 229910052799 carbon Inorganic materials 0.000 claims abstract 6
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims abstract 5
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims abstract 3
- AEOCXXJPGCBFJA-UHFFFAOYSA-N ethionamide Chemical compound CCC1=CC(C(N)=S)=CC=N1 AEOCXXJPGCBFJA-UHFFFAOYSA-N 0.000 claims abstract 3
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 3
- 230000003287 optical effect Effects 0.000 claims abstract 3
- 229920006395 saturated elastomer Polymers 0.000 claims abstract 3
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims abstract 2
- 125000003277 amino group Chemical group 0.000 claims 44
- 125000003545 alkoxy group Chemical group 0.000 claims 41
- -1 hydroxy, carboxyl Chemical group 0.000 claims 33
- 125000000753 cycloalkyl group Chemical group 0.000 claims 25
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 22
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 9
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 7
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 6
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 5
- 102220470957 Amiloride-sensitive sodium channel subunit delta_R21A_mutation Human genes 0.000 claims 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 4
- 125000004432 carbon atom Chemical group C* 0.000 claims 4
- 239000003795 chemical substances by application Substances 0.000 claims 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 4
- 238000002360 preparation method Methods 0.000 claims 4
- 125000001391 thioamide group Chemical group 0.000 claims 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 4
- 229920002554 vinyl polymer Polymers 0.000 claims 4
- 125000003342 alkenyl group Chemical group 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- 238000000034 method Methods 0.000 claims 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 125000006239 protecting group Chemical group 0.000 claims 3
- 125000006083 1-bromoethyl group Chemical group 0.000 claims 2
- 125000005999 2-bromoethyl group Chemical group 0.000 claims 2
- 125000005979 2-naphthyloxy group Chemical group 0.000 claims 2
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical group NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims 2
- 241000124008 Mammalia Species 0.000 claims 2
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims 2
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical group [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
- 208000010710 hepatitis C virus infection Diseases 0.000 claims 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 2
- 229940079322 interferon Drugs 0.000 claims 2
- 239000000543 intermediate Substances 0.000 claims 2
- 108090000765 processed proteins & peptides Proteins 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- 125000004963 sulfonylalkyl group Chemical group 0.000 claims 2
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims 1
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
- PAJPWUMXBYXFCZ-UHFFFAOYSA-N 1-aminocyclopropanecarboxylic acid Chemical group OC(=O)C1(N)CC1 PAJPWUMXBYXFCZ-UHFFFAOYSA-N 0.000 claims 1
- TXHAHOVNFDVCCC-UHFFFAOYSA-N 2-(tert-butylazaniumyl)acetate Chemical compound CC(C)(C)NCC(O)=O TXHAHOVNFDVCCC-UHFFFAOYSA-N 0.000 claims 1
- 239000004471 Glycine Substances 0.000 claims 1
- 241000711549 Hepacivirus C Species 0.000 claims 1
- 208000005176 Hepatitis C Diseases 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 102000014150 Interferons Human genes 0.000 claims 1
- 108010050904 Interferons Proteins 0.000 claims 1
- 102000005741 Metalloproteases Human genes 0.000 claims 1
- 108010006035 Metalloproteases Proteins 0.000 claims 1
- 108060004795 Methyltransferase Proteins 0.000 claims 1
- 102220479492 NAD(+) hydrolase SARM1_R22A_mutation Human genes 0.000 claims 1
- IWUCXVSUMQZMFG-AFCXAGJDSA-N Ribavirin Chemical compound N1=C(C(=O)N)N=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](CO)O1 IWUCXVSUMQZMFG-AFCXAGJDSA-N 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- 125000002015 acyclic group Chemical group 0.000 claims 1
- 125000001931 aliphatic group Chemical group 0.000 claims 1
- 125000005907 alkyl ester group Chemical group 0.000 claims 1
- DKNWSYNQZKUICI-UHFFFAOYSA-N amantadine Chemical compound C1C(C2)CC3CC2CC1(N)C3 DKNWSYNQZKUICI-UHFFFAOYSA-N 0.000 claims 1
- 229960003805 amantadine Drugs 0.000 claims 1
- 150000001413 amino acids Chemical class 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 239000012752 auxiliary agent Substances 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 239000003638 chemical reducing agent Substances 0.000 claims 1
- 230000008878 coupling Effects 0.000 claims 1
- 238000010168 coupling process Methods 0.000 claims 1
- 238000005859 coupling reaction Methods 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000001301 oxygen Chemical group 0.000 claims 1
- 150000003148 prolines Chemical class 0.000 claims 1
- 230000010076 replication Effects 0.000 claims 1
- 229960000329 ribavirin Drugs 0.000 claims 1
- HZCAHMRRMINHDJ-DBRKOABJSA-N ribavirin Natural products O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1N=CN=C1 HZCAHMRRMINHDJ-DBRKOABJSA-N 0.000 claims 1
- 229910052717 sulfur Chemical group 0.000 claims 1
- 239000011593 sulfur Chemical group 0.000 claims 1
- 238000003786 synthesis reaction Methods 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 150000003573 thiols Chemical class 0.000 claims 1
- 125000004665 trialkylsilyl group Chemical group 0.000 claims 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P13/00—Preparation of nitrogen-containing organic compounds
- C12P13/02—Amides, e.g. chloramphenicol or polyamides; Imides or polyimides; Urethanes, i.e. compounds comprising N-C=O structural element or polyurethanes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/08—Tripeptides
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- A61K38/16—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
- A61K38/17—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
- A61K38/19—Cytokines; Lymphokines; Interferons
- A61K38/21—Interferons [IFN]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/16—Antivirals for RNA viruses for influenza or rhinoviruses
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- 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
- C07D207/04—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 no double bonds between ring members or between ring members and non-ring members
- C07D207/10—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 no 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
- C07D207/16—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
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- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
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- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
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- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/08—Tripeptides
- C07K5/0802—Tripeptides with the first amino acid being neutral
- C07K5/0804—Tripeptides with the first amino acid being neutral and aliphatic
- C07K5/0806—Tripeptides with the first amino acid being neutral and aliphatic the side chain containing 0 or 1 carbon atoms, i.e. Gly, Ala
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- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/08—Tripeptides
- C07K5/0802—Tripeptides with the first amino acid being neutral
- C07K5/0804—Tripeptides with the first amino acid being neutral and aliphatic
- C07K5/0808—Tripeptides with the first amino acid being neutral and aliphatic the side chain containing 2 to 4 carbon atoms, e.g. Val, Ile, Leu
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- C07K5/08—Tripeptides
- C07K5/0802—Tripeptides with the first amino acid being neutral
- C07K5/0804—Tripeptides with the first amino acid being neutral and aliphatic
- C07K5/081—Tripeptides with the first amino acid being neutral and aliphatic the side chain containing O or S as heteroatoms, e.g. Cys, Ser
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- C12P41/00—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture
- C12P41/003—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture by ester formation, lactone formation or the inverse reactions
- C12P41/005—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture by ester formation, lactone formation or the inverse reactions by esterification of carboxylic acid groups in the enantiomers or the inverse reaction
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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Abstract
Racemati, dijastereoizomeri i optički izomeri jedinjenja formule (I) u kojoj B jeste H, grupa C6 ili C10 aril, C7-16 aralkil; Het ili (niži alkil)-Het, svaka od njih eventualno supstituisana sa c1-6 alkilom; C1-6 alkoksi; C1-6 alkanoil; hidroksi; hidroksialkil; halogena; halogenoalkil; nitro; cijana;, cijanoalkil; amino eventualno supstituisana sa C1-6 alkilom; amido; ili (niži alkil) amid; ili, B jeste acil derivat formule R4-C(O)-; karboksil formule R4-0-C(O)-; amid formule R4-N(R5)-C(O)-; tioamid formule R4-N (R5)-C(S)-; ili sulfonil formule R4-SO2; R5 je H ili C1-6 alkil; aY jeste H ili C1-6 alkil; R3 jeste C1-8 alkil, C3-7 cikloalkil, ili C4-10 alkilcikloalkil, sve eventualno supstituisane sa grupom hidroksi, C1-6 alkoksi, C1-6 tioalkil, amida, (niži alkil) amid, C6 ili C10 aril, ili C7-16 aralkil; R2 jeste CH2 –R20, NH –R20, O –R20 ili S –R20, gde R20 jeste zasićena ili nezasićena C3-7 cikloalkil ili C4-10 (alkilcikloalkil) grupa, sve eventualno mono-, di- ili tri-supstituisane sa R21, ili, R20 jeste C6 ili C10 aril ili C17-14 aralkil grupa, eventualno supstituisane, ili, R20 jeste Het ili (niži alkil)-Het, obe eventualno supstituisane, Het ili (niži alkil)-Het; karboksil; karboksi(niži alkil); C6 ili C10 aril, C7-14 aralkil ili Het, a pomenute aril, aralkil ili Het su eventualno supstituisani; a R 1 je H; C1-6 alkil, C3-7 cikloalkil, C2-6 alkenil, ili C2-6 alkinil, sve eventualno supstituisane sa halogenom; ili njegova farmaceutski prihvatljiva 20 so ili estar.
Claims (79)
1.Jedinjenje formule (I), njegovi racemati, dijastereoizomeri i optički izomeri formule u kojoj B je H, grupa C6 ili C10 aril, C7.1B aralkil; Het ili (niži alkil)-Het, svaka od njih eventualno supstituisana sa C^g alkilom; C^.g alkoksi; Cj.g alkanoil; hidroksi; hidroksialkil; halogeno; halogenoalkil; nitro; cijano; cijanoalkil; amino grupa eventualno supstituisana sa C].6 alkilom; amido; ili (niži alkil)amid; ili, B je karboksil formule R4-0-C(0)-; amid formule R4-N(Rs)-C(0)-; tioamid formule R4-N(R5)-C(S)-; ili sulfonil formule Rj-SC^gde R4 je grupa, (i) C^o alkil eventualno supstituisana sa grupom karboksil, C^g alkanoil, hidroksi, C]_6 alkoksi, amino eventualno mono- ili di-supstituisanom sa Ci_6 alkilom, amido ili (niži alkil)amid; (ii)C3.7 cikloalkil, C3.7 cikloalkoksi, ili C440 alkilcikloalkil, sve eventualno supstituisane sa grupom hidroksi, karboksil, (C^g alkoksi)karbonil, amino eventualno mono- ili di-supstituisanom sa Q.g alkilom, amido, ili (niži alkil)amid; (iii)amino eventualno mono- ili di-supstituisana sa Cj.g alkilom; amido; ili (niži alkil)amid; (iv)Cg ili Cjo aril ili C7.16 aralkil, sve eventualno supstituisane sa grupom C^g alkil, hidroksi, amido, (niži alkil)amid, ili amino eventualno mono- ili di-supstituisanom sa Cj.g alkilom; ili (v)Het ili (niži alkil)-Het, obe eventualno supstituisane sa grupom C^g alkil, hidroksi, amido, (niži alkil) amid, ili amino eventualno mono- ili di-supstituisanom sa Cj.g alkilom; R5 je H ili Cj.6 alkil; ili B je acil derivat formule I?4-C(0)-; gde R4 je grupa, (i) C^o alkil eventualno supstituisana sa grupom karboksil, Cj.g alkanoil, hidroksi, C^g alkoksi, ili amino eventualno mono- ili di-supstituisanom sa Ci_g alkilom; (ii)C3.7 cikloalkil, C3.7 cikloalkoksi, ili C^o alkilcikloalkil, sve eventualno supstituisane sa grupom hidroksi, karboksil, alkoksi) karbonil, ili amino eventualno mono- ili di-supstituisanom sa Cj.g alkilom; (iii)amino eventualno mono- ili di-supstituisana sa Ci_g alkilom; (iv)C6 ili C10 aril ili C7.16 aralkil, sve eventualno supstituisane sa grupom Ci„6 alkil, hidroksi, ili amino eventualno mono- ili di- supstituisanom sa Ci_6 alkilom; ili (v)Het ili (niži alkil)-Het, obe eventualno supstituisane sa grupom alkil, hidroksi, ili amino eventualno mono- ili di-supstituisanom sa Ci_6 alkilom; uz uslov, da kada B jeste amid ili tioamid, R4 nije cikloalkoksi grupa; a Y je H ili Cj.g alkil grupa; R3 je C^g alkil, C3.7 cikloalkil, ili C440 alkilcikloalkil, sve eventualno supstituisane sa grupom hidroksi, Cj.g alkoksi, Cj.g tioalkil, amido, (niži alkil) amido, Cg ili C10 aril, ili C7.16 aralkil; R2 je CH2 -R2o» NH -R20,0 -R20 ili S -R20, gde R20 jeste zasićena ili nezasićena C3.7 cikloalkil ili C4_10 (alkilcikloalkil) grupa, od kojih su sve eventualno mono- , di- ili tri-supstituisane sa R21, ili, R2o je C6 ili C10 aril ili C7.14 aralkil grupa, sve eventualno mono-, di- ili tri- supstituisane sa R2i, ili, R2o je Het ili (niži alkil)-Het, obe eventualno mono-, di- ili tri- supstituisane sa R2i, gde je svaka R24 nezavisno, grupa C4.g alkil; C4.6 alkoksi; niži tioalkil; sulfonil; N02; OH; SH; halogeno; halogenoalkil; amino eventualno mono- ili di-supstituisana sa grupom Cj.g alkil, C6 ili Cio aril, C7.14 aralkil, Het ili (niži alkil)-Het; amido eventualno mono-supstituisana sa grupom Cj.g alkil, C6 ili C10 aril, C7.]4 aralkil, Het ili (niži alkil)-Het; karboksil; karboksi(niži alkil); C6 ili C4o aril, C7.i4 aralkil ili Het, a pomenute aril, aralkil ili Het grupe su eventualno supstituisane sa R22; gde R22 je grupa C^g alkil; C3.7 cikloalkil; C^g alkoksi; amino eventualno mono- ili di-supstituisana sa C4.g alkilom; sulfonil; (niži alkil) sulfonil; N02; OH; SH; halogeno; halogenoalkil; karboksil; amid; (niži alkil) amid; ili Het eventualno supstituisan sa Ci_6 alkilom, R1 je H; grupa Cj.6 alkil, C3.7 cikloalkil, alkenil, ili C2.g alkinil, sve eventualno supstituisane sa halogenom; gde (niži) alkil, ili sam ili u kombinaciji sa drugim substituentom, označava ađklični, pravi ili razgranati lanac alkil supstituenata koji sadrže od 1 do 6 atoma ugljenika; amino aralkil, ili sam ili u kombinaciji sa drugim radikalom, označava amino grupu supstituisanu sa C746 aralkil grupom; (niži alkil)amid, ili sam ili u kombinaciji sa drugim radikalom, označava mono supstituisani amid sa Cj.g alkilom; karboksi (niži) alkil, ili sam ili u kombinaciji sa drugim radikalom, označava karboksilnu grupu (COOH) povezanu sa (nižom) alkil grupom kao što je gore definisano; Het je monovalentni radikal izveden uklanjanjem vodonika iz peto-, šesto- ili sedmočlanog zasićenog ili ne zasićenog (uključujući aromatičnog) heterocikla koji sadrži od jednog do četiri heteroatoma odabrana od azota, kiseonika ili sumpora, ili heterocikla kao što je gore definisano spojenog na jedan iE više drugih cikE; i (niži alkil)-Het je heterociklični radikal kao stoje gore definisano za Het vezan preko ravne iE razgranate alkil grupe, gde alkil kao što je gore definisano sadrži od 1 do 6 atoma ugljenika; iE njegova farmaceutski prihvatljiva so iE estar.
2.Jedinjenje formule I, prema zahtevu 1, iE njegova farmaceutski prihvatljiva so iE estar, gde Bje grupa C6 ili Cj0 aril, C7„16 aralkil, sve eventualno supstituisane sa grupom Ci_6 alkil, Cj.g alkoksi, C]_6 alkanoil, hiđroksi, hidroksialkil, halogeno, halogenoalkil, nitro, cijano, cijanoalkil, amido, (niži alkil) amido, iE amino, eventualno supstituisana sa C^g alkilom; iE B je grupa Het iE(niži alkil)-Het, sve eventualno supstituisane sa grupom Cw alkil, Cw alkoksi, Cw alkanoil, hiđroksi, hidroksialkil, halogeno, halogenoaEđl, nitro, cijano, cijanoaUdl, amido, (niži alkil) amido, iE amino grupa eventualno supstituisana sa C^g alkilom.
3.Jedinjenje formule I, prema zahtevu 1, iE njegova farmaceutski prihvatljiva so iE estar, gde B je R4-SO2, gde R4 jeste alkil; amido; (niži alkil) amid; C6 iE Cjo aril, C744 aralkil iE Het, sve eventualno supstituisane sa alkilom.
4.Jedinjenje formule I, prema zahtevu 1, iE njegova farmaceutski prihvatljiva so iE estar, gde B je acil derivat formule R4*C(0)-, gde je R4 grupa (i)C^o alkil eventualno supstituisana sa grupom karboksil, hiđroksi ili C]_6 alkoksi, ili amino grupom eventualno mono- ili di-supstituisanom sa Cj.g alkilom; (ii)C3.7 cikloalkil, ili C440 alkilcikloalkil, obe eventualno supstituisane sa grupom hiđroksi, karboksil, (Ci.g alkoksi)karbonil, ili amino grupom eventualno mono- ili di-supstituisanom sa Cj.g alkilom; (iv)C6 ili Cio aril ili C7_16 aralkil, sve eventualno supstituisane sa grupom Ci_6 alkil, hiđroksi, ili amino grupom eventualno supstituisanom sa C^g alkilom; (v)Het ili (niži alkil)-Het, obe eventualno supstituisane sa grupom Ci_6 alkil, hiđroksi, ili amino grupa eventualno supstituisana sa C^g alkilom.
5.Jedinjenje formule I, prema zahtevu 1, ili njegova farmaceutski prihvatljiva so ili estar, gde Bje karboksil formule I?4-0-C(0)-, gde je R4 grupa (i)Ci_i0 alkil eventualno supstituisana sa grupom karboksil, Ci.g alkanoil, hiđroksi, C].6 alkoksi, amino eventualno mono- ili di- supstituisanom sa grupom C^g alkil, amido ili (niži alkil) amid; (ii)C3.7 cikloalkil, C^o alkilcikloalkil, sve eventualno supstituisane sa grupom karboksil, (Cj.g alkoksi) karbonil, amino eventualno mono- ili di- supstituisanom sa grupom C^g alkil, amido ili (niži alkil)amid; (iv)C6 ili Cio aril ili C7_16 aralkil, eventualno supstituisane sa grupom Ci_g alkil, hiđroksi, amido, (niži alkil) amido, ili amino grupom eventualno mono- ili di-supsti-tuisanom sa C^g alkilom; ili (v)Het ili (niži alkil)-Het, obe eventualno supstituisane sa grupom Ci_6 alkil, hiđroksi, amino eventualno mono- ili di-supstituisanom sa grupom Cj.g alkil, amido ili (niži alkil) amido.
6.Jedinjenje formule I, prema zahtevu 1, ili njegova farmaceutski prihvatljiva so ili estar, gde B je amid formule R4-N(Rs)-C(0)-, gde je R* grupa (0 C1-10 alkil eventualno supstituisana sa grupom karboksil, Ci.g alkanoil, hiđroksi, Cj.g alkoksi, amido, (niži alkil) amido, ili amino grupom eventualno mono- ili di-supstituisanom sa C^g alkilom; (ii)C3.7 cikloalkil ili C^o alkilcikloalkil, sve eventualno supstituisane sa grupom karboksil, (C^g alkoksi)karbonil, amido, (niži alkil) amido, ili amino grupom even-tualno mono- ili di-supstituisanom sa C^g alkilom; (iii)amino eventualno mono- ili di-supstituisana sa Ci_3 alkilom; (iv)Cg ili Cjo aril ili C7.16 aralkil, sve eventualno supstituisane sa grupom C^g alkil, hiđroksi, amido, (niži alkil) amid, ili amino grupom eventualno supstituisanom sa C^g alkilom; ili (v) Het ili (niži alkil)-Het, obe eventualno supstituisane sa grupom Ci_6 alkil, hidroksi, amino eventualno supstituisanom sa grupom Cj.g alkil, amido ili (niži alkil) amid; a Rsje H ili metil grupa.
7.Jedinjenje formule I, prema zahtevu 1, ili njegova farmaceutski prihvatljiva so ili estar, gde B je tioamid formule Rj-NH-CfS)-, gde je R4 grupa (i)C140 alkil eventualno supstituisan sa grupom karboksil, Cj.g alkanoil ili Cj.g alkoksi; (ii)C3.7 cikloalkil ili C^io alkilcikloalkil, sve supstituisane sa grupom karboksil, (Ci_g alkoksi)karbonil, amino ili amido.
8.Jedinjenje formule I, prema zahtevu 2, ili njegova farmaceutski prihvatljiva so ili estar, gde B je grupa Cg ili Cjo aril eventualno supstituisana sa grupom Cj.g alkil, Ci_6 alkoksi, Ci_g alkanoil, hidroksi, hidroksialkil, halogeno, halogenoalkil, nitro, cijano, cijanoalkil, amido, (niži alkil) amid, ili amino grupom eventualno mono- ili di-supstituisanom sa Ci_g alkilom.
9.Jedinjenje formule I, prema zahtevu 2, ili njegova farmaceutski prihvatljiva so ili estar, gde B je Het grupa, eventualno supstituisana sa grupom Cj.g alkil, Cj. 6 alkoksi, C^g alkanoil, hidroksi, halogeno, amido, (niži alkil) amid, ili amino grupom eventualno mono- ili di- supstituisanom sa Ci_6 alkilom.
10.Jedinjenje formule I, prema zahtevu 4, ili njegova farmaceutski prihvatljiva so ili estar, gde B je acil derivat formule R4-C(0)- gde je R4 grupa (i)C140 alkil eventualno supstituisana sa grupom karboksil, hidroksi ili Cj.g alkoksi; ili (ii)C3.7 cikloalkil ili C^o alkilcikloalkil, obe eventualno supstituisane sa grupom hidroksil, karboksil, (C^g alkoksi)karbonil, ili (iv)Cg ili Cio aril Hi C7.16 aralkil, sve eventualno supstituisane sa grupom Ci_6 alkil, hidroksi, ili (v)Het, eventualno supstituisana sa grupom C^g alkil, hidroksi, amido ili amino.
11.Jedinjenje formule I, prema zahtevu 5, ili njegova farmaceutski prihvatljiva so ili estar, gde B je karboksil formule Ri-O-CfO)-, gde je Rj grupa (0 C1-10 alkil eventualno supstituisan sa grupom karboksil, Ci_6 alkanoil, hidroksi, Ci_6 alkoksi ili amido, (niži alkil)amid, amino grupom eventualno mono- ili di-supstituisanom sa Cj.g alkilom; (ii) C3.7 cikloalkil, C440 alkilcikloalkil, sve eventualno supstituisane sa grupom karboksil, (Cj.g alkoksi)karbonil, amido, (niži alkil)amid, amino grupom eventualno mono- ili di-supstituisanom sa C^g alkilom, ili (iv) C6 ili Cio aril Hi C7.16 aralkil, sve eventualno supstituisane sa grupom Ci_6 alkil, hidroksi, amino grupom eventualno supstituisanom sa C^e alkilom; ili (v) Het ili (niži alkil)-Het, obe eventualno supstituisane sa grupom Cj.g alkil, hidroksi, amido, ili amino grupom eventualno mono-supstituisanom sa Cj.g alkilom.
12.Jedinjenje formule I, prema zahtevu 6, ili njegova farmaceutski prihvatljiva so ili estar, gde B je amid formule R4-N(R5)-C(0)-, gde je R4 grupa (i)C|.10 alkil eventualno supstituisana sa grupom karboksil, C^g alkanoil, hidroksi, Cx.g alkoksi, amido, (niži alkil)amid, amino grupom eventualno mono- ili di-supstituisanom sa Cs_6 alkilom; (ii)C3.7 cikloalkil ili C4.10 alkilcikloalkil, sve eventualno supstituisane sa grupom karboksil, (C^g alkoksi)karbonil, amido, (niži alkil)amid, amino grupom eventualno mono- ili di-supstituisanom sa Cj.g alkilom; (iii)amino grupa eventualno mono- ili di-supstituisana sa Ci_3 alkilom, ili (iv)Cg ili C10 aril ili C7.16 aralkil, sve eventualno supstituisane sa grupom Ci_g alkil, hidroksi, amino ili amido eventualno supstituisanom sa Cj.g alkilom; ili (v)Het eventualno supstituisan sa grupom Ci.6 alkil, hidroksi, amino ili amido, a R5 je H.
13.Jedinjenje formule I, prema zahtevu 7, ili njegova farmaceutski prihvatljiva so ili estar, gde B je tioamid formule Rj-NH-CtS)-; gde je R4 grupa (i) CM0 alkil; ili (ii) C3.7 cikloalkil.
14.Jedinjenje formule I, prema zahtevu 12, ili njegova farmaceutski prihvatljiva so ili estar, gde B je amid formule R4-NH-C (0)-, gde je R4 grupa (0 C1-10 alkil eventualno supstituisana sa grupom karboksil, Cj.g alkanoil, hidroksi, alkoksi, amido, (niži alkil) amid, amino grupom eventualno mono- ili di-supstituisanom sa Cj.g alkilom; (ii) Cg.7 cikloalkil ili C440 alkilcikloalkil, sve eventualno supstituisane sa grupom karboksil, (Cj.g alkoksi)karbonil, amido, (niži alkil)amid, amino grupom eventualno mono- ili di- supstituisanom sa C^g alkilom; (iv) Cg ili C10 aril ili C7.16 aralkil eventualno supstituisana sa grupom Ci_g alkil, hidroksi, amino ili amido.
15.Jedinjenje formule I, prema zahtevu 1, ili njegova farmaceutski prihvatljiva so ili estar, gde Bje
16.Jedinjenje formule I, prema zahtevu 1, ili njegova farmaceutski prihvatljiva so ili estar, gde Y je H ili metil.
17.Jedinjenje formule I, prema zahtevu 16, ili njegova farmaceutski prihvatljiva so ili estar, gde Y je H.
18.Jedinjenje formule I, prema zahtevu 1, ili njegova farmaceutski prihvatljiva so ili estar, gde R3 je grupa Cj.g alkil, C3.7 cikloalkil, ili C440 alkilcikloalkil, sve eventualno supstituisane sa grupom hidroksi, C4_g alkoksi, C4.g tioalkil, acetamido, Cg ili C4o aril ili C7.ig aralkil.
19.Jedinjenje formule 1, prema zahtevu 18, ili njegova farmaceutski prihvatljiva so ili estar, gde R3 je bočni lanac fe/r-butil-glicina (Tbg), Ile, Val, Chg ili:
20.Jedinjenje formule I, prema zahtevu 19, ili njegova farmaceutski prihvatljiva so ili estar, gde R3 je bočni lanac Tbg, Chg ili Val.
21.Jedinjenje formule I, prema zahtevu 1, ili njegova farmaceutski prihvatljiva so ili estar, gde R2 je S-R20 ili O-R20, gde R2o jeste C6 ili Cjo aril, C7.16 aralkil, Het ili -CH2-Het, sve grupe eventualno mono-, di- ili tri-supstituisane sa R2i, gde R2i je grupa C4_6 alkil; C^g alkoksi; niži tioalkil; amino eventualno mono- ili di-supstituisane sa grupom Ci_6 alkil, amido eventualno mono- supstituisan sa grupom Cj.g alkil, C6 ili C10 aril, C7_14 aralkil, Het ili (niži alkil)-Het grupom; N02; OH; halogeno; trifluorometil; karboksil; C6 ili C4o aril, C7_i4 aralkil, ili Het, a pomenute aril, aralkil ili Het eventualno su supstituisane sa R22, gde R22 je grupa C|.fi alkil; Cg_7 cikloalkil; C^g alkoksi; amino eventualno mono- ili di-supstituisane sa C^g alkilom; (niži alkil) amid; sulfonilalkil; N02; OH; halogeno; trifluorometil; karboksil ili Het.
22.Jedinjenje formule I, prema zahtevu 21, ili njegova farmaceutski prihvatljiva so ili estar, gde R24 jeste grupa Cj.g alkil; Cj.g alkoksi; amino; di-(niži alkil)amino; (niži alkil)amid; C6 ili C10 aril, ili Het, a pomenute aril ili Het eventualno su supstituisane sa R22, gde R22 jeste grupa C^g alkil; C3_7 cikloalkil; C^g alkoksi; amino; mono- ili di(niži alkil)amino; amido; (niži alkil)amid; halogeno; trifluoromelil ili Het.
23.Jedinjenje formule I, prema zahtevu 22, ili njegova farmaceutski prihvatljiva so ili estar, gde R22 jeste grupa C^g alkil; Ci_g alkoksi; halogeno; amino eventualno mono- ili di- supstituisana sa nižim alkilom; amido; (niži alkil)amid; ili Het.
24.Jedinjenje formule I, prema zahtevu 1, ili njegova farmaceutski prihvatljiva so ili estar, gde R22 jeste grupa metil; etil; izopropil, terc-butil; metoksi; hloro; amino eventualno mono- ili di-supstituisana sa nižim alkilom; amido, (niži alkil) amid; ili (niži alkil) 2-tiazol.
25.Jedinjenje formule I, prema zahtevu 21, ili njegova farmaceutski prihvatljiva so ili estar, gde R2 je odabran iz grupe koju čine:
26.Jedinjenje formule I, prema zahtevu 21, ili njegova farmaceutski prihvatljiva so ili estar, gde R2 je grupa 1-naftilmetoksi; 2-naftilmetoksi; benziloksi, 1- naftiloksi; 2-naftiloksi; ili hinolinoksi, nesupstituisana, mono- ili di- supstituisana sa R21 kao što je definisano u zahtevu 21.
27.Jedinjenje formule I, prema zahtevu 26, ili njegova farmaceutski prihvatljiva so ili estar, gde R2 je grupa 1-naftilmetoksi; ili hinolinoksi, nesupstituisana, mono- ili di-supstituisana sa R21 kao što je definisano u zahtevu 21.
28.Jedinjenje formule I, prema zahtevu 27, ili njegova farmaceutski prihvatljiva so ili estar, gde R2 je odabran iz grupe koja se sastoji od:
29.Jedinjenje formule I, prema zahtevu 26, ili njegova farmaceutski prihvatljiva so ili estar, gde R2 je: gde je R21A grupa Ci_6 alkil; Ci.g alkoksi; niži tioalkil; halogeno; amino eventualno mono-supstituisana sa C].g alkilom; ili Cg ili Cjo aril, C745 aralkil, ili Het, a pomenuti aril, aralkil ili Het eventualno su supstituisani sa R22, gde je R22 grupa alkil, C^g alkoksi, amido, (niži alkil)amid, amino eventualno mono- ili di-supstituisana sa C^g alkilom, ili Het; a R21B je grupa C^g alkil, Cj.g alkoksi, amino, difC^g alkil)amino, (niži alkil) amid, NO2, OH, halogeno, trifluorometil ili karboksil.
30.Jedinjenje formule I, prema zahtevu 29, ili njegova farmaceutski prihvatljiva so ili estar, gde je R21A grupa Cg ili C10 aril ili Het, sve eventualno supstituisane sa R22 kao što je definisano u zahtevu 29.
31.Jedinjenje formule I, prema zahtevu 30, ili njegova farmaceutski prihvatljiva so ili estar, gde je R21A odabran iz grupe koju čine:
32.Jedinjenje formule I, prema zahtevu 29, ili njegova farmaceutski prihvatljiva so ili estar, gde R2 je: gde R22A je C^g alkil; C^g alkoksi; ili halogeno; a R2ib je Cj.g alkil, C^g alkoksi, amino, di(niži alkil) amino, (niži alkil)amid, N02, OH, halogeno, trifluorometil, ili karboksil grupa.
33.Jedinjenje formule I, prema zahtevu 29, ili njegova farmaceutski prihvatljiva so ili estar, gde R2 je: gde je R22B grupa C^g alkil, amino grupa eventualno mono-supstituisana sa grupom C^g alkil, amido, ili (niži alkil) amidom; a R21B je grupa Cj.g alkil, C^g alkoksi, amino, di(niži alkil)amino, (niži alkil)amid, NO2, OH, halogeno, trifluorometil ili karboksil.
34.Jedinjenje formule I, prema zahtevu 32 ili 33, ili njegova farmaceutski prihvatljiva so ili estar, gde R21B je grupa Ci_6 alkoksi, ili di (niži alkil) amino.
35.Jedinjenje formule I, prema zahtevu 32 ili 33, ili njegova farmaceutski prihvatljiva so ili estar, gde R21B je metoksi.
36.Jedinjenje formule I, prema zahtevu 1, ili njegova farmaceutski prihvatljiva so ili estar, gde P1 je ciklobutil ili ciklopropil prsten, oba eventualno supstituisana sa Ri, gde Ri je H, Cw alkil, C3.5 cikloalkil, ili C2.4 alkenil, sve eventualno supstituisane sa halogenom.
37.Jedinjenje formule I, prema zahtevu 36, ili njegova farmaceutski prihvatljiva so ili estar, gde P1 je ciklopropil a Rj je etil, vinil, ciklopropil, 1 ili 2-bromoetil ili 1 ili 2-bromovinil.
38.Jedinjenje formule I, prema zahtevu 37, ili njegova farmaceutski prihvatljiva so ili estar, gde Ri je vinil.
39.Jedinjenje formule I, prema zahtevu 37, ili njegova farmaceutski prihvatljiva so ili estar, gde je Rj na ugljeniku 2 orijentisan syn u odnosu na karbonil u položaju 1, prikazano pomoću radikala:
40.Jedinjenje formule I, prema zahtevu 37, ili njegova farmaceutski prihvatljiva so ili estar, gde je Ri u položaju 2 orijentisan anti u odnosu na karbonil u položaju 1, prikazano pomoću radikala:
41.Jedinjenje formule I, prema zahtevu 37, ili njegova farmaceutski prihvatljiva so ili estar, gde ugljenik 1 ima R konfiguraciju:
42.Optički izomer jedinjenja formule I, prema zahtevu 41, ili njegova farmaceutski prihvatljiva so ili estar, gde pomenuti Ri supstituent i karbonil jesu u syn orijentaciji sa sledećom apsolutnom konfiguracijom:
43.Jedinjenje formule I, prema zahtevu 42, ili njegova farmaceutski prihvatljiva so ili estar, gde Ri je etil, stoga asimetrični atomi ugljenika u položajima 1 i 2 imaju R,R konfiguraciju.
44.Jedinjenje formule I, prema zahtevu 42, ili njegova farmaceutski prihvatljiva so ili estar, gde Rj je vinil, stoga asimetrični atomi ugljenika u položajima 1 i 2 imaju R,S konfiguraciju.
45.Jedinjenje formule I, prema zahtevu 1, ili njegova farmaceutski prihvatljiva so ili estar, gde B je grupa Cq ili Cjo aril ili Cy.16 aralkil, sve eventualno supstituisane sa grupom Cj.6 alkil, C^6 alkoksi, Cj_6 alkanoil, hidroksi, hiđroksialkil, halogeno, halogenoalkil, nitro, cijano, cijanoalkil, amido, (niži alkil) amido, ili amino grupom eventualno supstituisanom sa Ci_6 alkilom; ili Het ili (niži alkil)-Het, sve eventualno supstisuisane sa grupom Cj.g alkil, Cj_6 alkoksi, Cj.6 alkanoil, hidroksi, hiđroksialkil, halogeno, halogenoalkil, nitro, cijano, cijanoalkil, amido, (niži alkil) amido, ili amino eventualno supstituisanom sa Ci.g alkilom; ili B je R4-SO2 gde je R4 prvenstveno grupa amido; (niži alkil)amid; C6 ili Cjo aril, C744 aralkil ili Het, sve eventualno supstituisane sa Ci_g alkilom, ili B je acil derivat formule R4 -C(O)- gde R4 jeste grupa (i)alkil eventualno supstituisana sa grupom karboksil, hidroksi ili C^.g alkoksi, ili amino grupom eventualno mono- ili di-supstituisanom sa C1.6 alkilom; (ii)C3.7 cikloalkil ili C440 alkilcikloalkil, obe eventualno supstituisane sa grupom hidroksi, karboksil, (C^g alkoksi) kabonil, ili amino grupom eventualno mono- ili di-supstituisanom sa C^g alkilom; (iv)Cg ili Cio aril ili C7_ig aralkil, sve eventualno supstituisane sa grupom Ci_g alkil, hidroksi, ili amino grupom eventualno supstituisanom sa C^g alkilom; (v)Het ili (niži alkil)-Het, obe eventualno supstituisane sa grupom Ci.g alkil, hidroksi, amino grupom eventualno supstituisanom sa grupom Ci_6 alkil, ili amino grupa eventualno supstituisana sa C^g alkilom, ili B je karboksil formule R4 -O-C(O)-, gde R4 jeste grupa (i)Cno alkil eventualno supstituisana sa grupom karboksil, Ci.6 alkanoil, hidroksi, C^g alkoksi, amino grupom eventualno mono- ili di-supstituisanom sa grupom Ci_6 alkil, amido ili (niži alkil) amid; (ii)C3.7 cikloalkil, C440 alkilcikloalkil, sve eventualno supstituisane sa grupom karboksil, (Cj.g alkoksi) karbonil, amino grupom eventualno mono- ili di-supstituisanom sa grupom C^g alkil, amido ili (niži alkil) amid; (iv)Cg ili Cio aril ili C740 aralkil, eventualno supstituisane sa grupom Ci„6 alkil, hidroksi, amido, (niži alkil)amido, ili amino grupom eventualno mono- ili di-supstituisanom sa C^g alkilom; ili (v)Het ili (niži alkil)-Het, obe eventualno supstituisane sa grupom Ci.g alkil, hidroksi, amino grupom eventualno mono- ili di-supstituisanom sa grupom C^g alkil, amido ili (niži alkil) amido, ili B je amid formule R4-N(Rg)-C(0)-, gde R4 je grupa (i)Cj.io alkil eventualno supstituisana sa grupom karboksil, Ci.g alkanoil, hidroksi, Ci_6 alkoksi, amido, (niži alkil)amido, ili amino grupom eventualno mono- ili di-supstituisanom sa C^g alkilom; (ii)C3.7 cikloalkil ili C440 alkilcikloalkil, sve eventualno supstituisane sa grupom karboksil, (C^g alkoksi) karbonil, amido, (niži alkil) amido, ili amino grupom eventualno mono- ili di-supstituisanom sa C^g alkilom; (iii)amino eventualno mono- ili di-supstituisana sa C^ alkilom; (iv)C6 ili C10 aril ili C7.16 aralkil, sve eventualno supstituisane sa grupom Ci_6 alkil, hidroksi, amido, (niži alkil)amid, ili amino grupom eventualno supstituisanom sa Ci_g alkilom; ili (v)Het ili (niži alkil)-Het, obe eventualno supstituisane sa grupom C^g alkil, hidroksi, amino grupom eventualno supstituisanom sa grupom Cj.g alkil, amido ili (niži alkil)amid; a R5 je H ili metil grupa, ili B je tioamid formule R4-NH-C(S)-, gde R4 je grupa (i)C'i40 alkil eventualno supstituisana sa grupom karboksil, Cj_6 alkanoil ili C1.6 alkoksi; (ii)C3.7 cikloalkil ili C440 alkilcikloalkil, sve supstituisane sa grupom karboksil, (Cj.g alkoksi)karbonil, amino ili amido; Y jeste H ili metil grupa; R3 je grupa C4.g alkil, C3.7 cikloalkil, ili C^o alkilcikloalkil, sve eventualno supstituisane sa grupom hidroksi, C].g alkoksi, C^g tioalkil, acetamido, Cg ili C10 aril ili C7.16 aralkil; R2 je S-R2o ili O-R20, gde R20 jeste prvenstveno C6 ili C10 aril, C^g aralkil, Het ili -CH2-Het, sve grupe eventualno mono-, di- ili tri-supstituisane sa R21, gde R21 je grupa Ci_6 alkil; C^g alkoksi; niži tioalkil; amino ili amido eventualno mono- ili di-supstituisane sa grupom Cj.g alkil, C6 ili C10 aril, C7.16 aralkil, Het ili (niži alkil)-Het; NO2; OH; halogeno; trifluorometil; karboksil; C6 ili Cio aril, C7.ig aralkil, ili Het, a pomenute aril, aralkil ili Het eventualno su supstituisane sa R22, gde R22 je grupa C^g alkil; C3.7 cikloalkil; C^g alkoksi; amino; mono- ili di-(niži alkil)amino; (niži alkil)amid; sulfonilalkil; NO2; OH; halogeno; trifluorometil; karboksil ili Het; ili R2 je odabran iz grupe koja se sastoji od: ili R2 je 1-naftilmetoksi; 2-naftilmetoksi; benziloksi, 1-naftiloksi; 2-naftiloksi; ili hinolinoksi, nesupstituisana, mono- ili di-supstituisana sa R21 kao što je gore definisano; a P1 segment je ciklobutil ili ciklopropil prsten, oba eventualno supstituisana sa Ri, gde Ri je grupa C^ alkil, C3.5 cikloalkil ili C2.4 alkenil eventualno supstituisana sa halogenom, a pomenuti Rx na ugljeniku 2 orijentisan je syn u odnosu na karbonil u položaju 1, što je prikazano pomoću radikala: ili njegova farmaceutski prihvatljiva so ili estar.
46. Jedinjenje formule I, prema zahtevu 45, ili njegova farmaceutski prihvatljiva so ili estar, gde je B grupa Cg ili C1() aril, eventualno supstituisane sa grupom Ci_6 alkil, Ci.6 alkoksi, C^g alkanoil, hidroksi, hidroksialkil, halogeno, halogenoalkil, nitro, cijano, cijanoalkil, amido, (niži alkil)amid, ili amino grupom eventualno mono- ili di-supstituisanom sa Ci_g alkilom; ili B je Het eventualno supstituisan sa grupom C].g alkil, Ci_g alkoksi, Cj.g alkanoil, hidroksi, halogeno, amido, (niži alkil) amid, ili amino grupom eventualno mono- ili di-supstituisanom sa C^g alkilom; ili B je R4-SO2 gde R4 je C6 ili C10 aril, C744 aralkil ili Het svi eventualno supstituisani sa C^g alkilom; amido; (niži alkil) amid; B je acil derivat formule R4 -C (0)- gde je R4 grupa (i)C],10 alkil eventualno supstituisana sa grupom karboksil, hidroksi ili C]_6 alkoksi; ili (ii)C3.7 cikloalkil ili C440 alkilcikloalkil, obe eventualno supstituisane sa grupom hidroksi, karboksil, (Cj.g alkoksi)kabonil; ili (iv)C6 ili Cio aril ili C7.16 aralkil, sve eventualno supstituisane sa grupom Ci.6 alkil, hidroksi; ili (v)Het eventualno supstituisan sa grupom Cj.g alkil, hidroksi ili amino; ili B je karboksil formule R4 -O-C(O)-, gde je R4 grupa (i)Cj.jo alkil eventualno supstituisan sa grupom karboksil, Cj.g alkanoil, hidroksi, C^g alkoksi, ili amido, (niži alkil)amid, amino eventualno mono- ili di-supstituisanom sa C^g alkilom; (ii)C3.7 cikloalkil, C440 alkilcikloalkil, sve eventualno supstituisane sa grupom karboksil, (C^g alkoksi)karbonil, amido, (niži alkil) amid, amino eventualno mono- ili di-supstituisanom sa Cj.g alkilom; ili (iv) Cg ili Cio aril ili C745 aralkil, sve eventualno supstituisane sa grupom Ci_6 alkil, hidroksi, amino eventualno supstituisanom sa Ci.g alkilom; ili (v) Het ili (niži alkil)-Het, obe eventualno supstituisane sa grupom Ci.q alkil, hidroksi, amido, ili amino eventualno mono-supstituisanom sa Ci_6 alkilom; ili B je amid formule R4-N (R5)-C(0)-, gde je R4 grupa 0) C1-10 alkil eventualno supstituisana sa grupom karboksil, Ci_g alkanoil, hidroksi, C^g alkoksi, amido, (niži alkil) amid, amino eventualno mono- ili di-supstituisanom sa C^g alkilom; (ii) C3.7 cikloalkil ili C440 alkilcikloalkil, sve eventualno supstituisane sa grupom karboksil, (Ci_6 alkoksi) karbonil, amido, (niži alkil)amid, amino eventualno mono- ili di-supstituisanom sa Cj.g alkilom; a R5 je H ili metil; ili R4 je (iii) amino eventualno mono- ili di-supstituisana sa C^ alkilom; ili (iv)C6 ili Cio anl ili C7.16 aralkil, sve eventualno supstituisane sa grupom C^g alkil, hidroksi, amino ili amido eventualno supstituisanom sa C^g alkilom; ili (v)Het eventualno supstituisan sa grupom C^g alkil, hidroksi, amino ili amido; ili Bje tioamid formule R4-NH-C(S)-, gde je R4 grupa (i) CM0 alkil; ili (ii) C3.7 cikloalkil; ili YjeH; R3 je bočni lanac u terc-butilglicinu (Tbg), Ile, Val, Chg, ili: R2 je 1-naftilmetoksi; ili hinolinoksi, nesupstituisan, mono- ili di-supstituisan sa R21, kao što je definisano gore, ili R2 je: gde R2iAje grupa C^g alkil; C]_6 alkoksi; C6, C10 aril ili Het; niži tioalkil; halogeno; amino eventualno mono-supstituisana sa C^g alkilom; ili Cg, Cio aril» C7.ig aralkil ili Het, eventualno supstituisan sa R22 gde R22 je Ci_6 alkil, C^g alkoksi, amido, (niži alkil) amid, amino eventualno mono- ili di- supstituisana sa C^g alkilom, ili Het; P1 je ciklopropil prsten u kome ugljenik 1 ima R konfiguraciju, a R1 je etil, vinil, ciklopropil, 1 ili 2-bromoetil ili 1 ili 2-bromovinil.
47.Jedinjenje formule I, prema zahtevu 46, ili njegova farmaceutski prihvatljiva so ili estar, gde B je amid formule R4 -NH-C(O)- gde je R* grupa (i)C1-10 alkil eventualno supstituisana sa grupom karboksil, Ci_6 alkanoil, hidroksi, C}.g alkoksi, amido, (niži alkil) amid, amino eventualno mono- ili di-supstituisanom sa C^.g alkilom; (ii)C3.7 cikloalkil ili C440 alkilcikloalkil, sve eventualno supstituisane sa grupom karboksil, (Ci_g alkoksi)karbonil, amido, (niži alkil) amid, amino eventualno mono- ili di-supstituisanom sa Ci_6 alkilom; (iv) Cg ili C10 aril ili C7.16 aralkil, eventualno supstituisane sa grupom Cj.g alkil, hidroksi, amino ili amido; R3 je bočni lanac u Tbg, Chg ili Val; R2ie: gde R22A Je grupa Ci.6 alkil (kao stoje metil); Cj.g alkoksi (kao što je metoksi); ili halogeno (kao što je hloro); R22B je grupa Cj_6 alkil, amino grupa eventualno mono-supstituisana sa grupom C^g alkil, amido ili (niži alkil) amid; a R2ib je C^g alkil, Cj.g alkoksi, amino, di (niži alkil) amino, (niži alkil) amid, N02, OH, halogeno, trifluorometil, ili karboksil; a P1 je:
48.Jedinjenje prema zahtevu 45, prikazano formulom u kojoj B, R3, R.2, imaju značenje kao što je niže definisano:
49.Jedinjenje # 111, prema zahtevu 48.
50.Jedinjenje prema zahtevu 45, prikazano formulom:
51.u kojoj B, R3, R2, Ri imaju značenje kao što je niže definisano: Jedinjenje # 203 prema zahtevu 50.
52.u kojoj B, R3, R2 i Ri imaju značenje kao što je niže definisano: Jedinjenje prema zahtevu 45, prikazano formulom:
53.Jedinjenje prema zahtevu 52, odabrano iz grupe koju sačinjavaju jedinjenja #: 307,314, 317,319,321,324, 325, 326,327,329,331, 332,333 i 334.
54.Jedinjenje prema zahtevu 1, prikazano formulom:
55.Jedinjenje prema zahtevu 54, odabrano iz grupe koju sačinjavaju jedinjenja #: 403,405 i 406.
56.Jedijenje prema zahtevu 45, prikazano formulom:
57.Jedinjenje prema zahtevu 56, odabrano iz grupe koju sačinjavaju jedinjenja #: 501,509 i 510.
58.Jedinjenje prema zahtevu 46, prikazano formulom:
59.Jedinjenje prema zahtevu 58, odabrano iz grupe koju sačinjavaju jedinjenja #: 601, 602, 603, 604, 605, 606, 607, 610, 611, 612, 615, 616, 617, 620, 621, 622, 625,626, 627,628,629 i 630.
60.Jedinjenje prema zahtevu 46, prikazano formulom: u kojoj R3 i R21A imaju značenje kao što je đefinisano dole:
61.Jedinjenje prema zahtevu 60, izabrano iz grupe koju sačinjavaju jedinjenja #: 701,702, 703,704,705, 706, 707, 708,709 i 711 do 737.
62.Jedinjenje prema zahtevu 45, prikazano formulom: u kojoj B, R3 i R22 imaju značenje kao što je definisano dole:
63.Jedinjenje prema zahtevu 62, izabrano iz grupe koju sačinjavaju jedinjenja #: 801 do 825,827 do 858 i 860 do 873.
64.Jedinjenje prema zahtevu 45, prikazano formulom: u kojoj B ima značenje kao što je definisano dole:
65.Jedinjenje prema zahtevu 45, prikazano formulom: u kojoj B, X, R3, z i R21B imaju značenje kao što je definisano dole:
66.Farmaceutska kompozicija koja sadrži anti-hepatitis C virusno efikasnu količinu jedinjenja formule I, prema zahtevu 1, ili njegovu terapeutski prihvatljivu so ili estar, u smeši sa farmaceutski prihvatljivim nosećim medijumom ili pomoćnim sredstvom.
67.Jedinjenje formule I prema jednom od zahteva 1 do 65, kao medikament.
68.Primena jedinjenje formule I prema zahtevu 1, ili njegove terapeutski prihvatljive soli ili estra ili farmaceutske kompozicije prema zahtevu 66 za pripremanje medikamenta za lečenje virusne infekcije hepatitisa C kod sisara.
69.Primena jedinjenje formule I prema zahtevu 1, ili njegove terapeutski prihvatljive soli ili estra za pripremu farmaceutske kompozicije za inhibiranje replikacije virusa hepatitisa C.
70.Primena kombinacije jedinjenja formule I prema zahtevu 1, ili njegove terapeutski prihvatljive soli ili estra sa drugim anti-HCV sredstvom za pripemanje medikamenta za lečenje virusne infekcije hepatitisa C kod sisara.
71.Primena prema zahtevu 70, gde navedeno drugo anti-HCV sredstvo je interferon.
72.Primena prema zahtevu 70 ili 71, gde je navedeno drugo anti-HCV sredstvo odabrano iz grupe koju čine: a- ili (3-interferon, ribavirin i amantadin.
73.Primena prema zahtevu 70, gde navedeno drugo anti-HCV sredstvo sadrži inhibitor drugih ciljeva u životnom ciklusu HCV-a, odabranom između: helikaze, polimeraze, metaloproteaze ili IRES.
74.Postupak za pripremanje jedinjenja prema zahtevu 1, gde P1 jeste ostatak supstituisane aminociklopropil-karboksilne kiseline, što sadži stupanj: kuplovanja peptida odabranog iz grupe koju čine: APG-P3-P2; ili APG-P2; sa intermedijerom Pl, formule: u kojoj Ri jeste grupa C]_6 alkil, cikloalkil ili C2.$ alkenil, sve eventualno supstituisane sa halogenom, CPG je zaštitna grupa karboksila, APG je zaštitna grupa amino radikala, a P3 i P2 imaju značenje kao što je gore definisano.
75.Primena P1 intermedijera formule: u kojoj Rx jeste grupa C^g alkil, cikloalkil ili C2_6 alkenil, sve eventualno supstituisane sa halogenom a CPG je zaštitna grupa karboksila za pripremanje jedinjenja formule I kao što je gore definisano.
76.Amino kiselina analognog jedinjenja formule:
77.Postupak prema zahtevu 74, gde pomenuta zaštitna grupa karboksila (CPG) jeste izabrana iz grupe koju čine: alkil estri, aralkil estri, a estri koji se razlazu tretmanom pomoću blage baze ili blagog redukcionog sredstva
78.Postupak prema zahtevu 74, gde pomenuta zaštitna grupa amino rađikala (APG) jeste izabrana iz grupe koju čine: acil grupe, aromatične karbamatne grupe, alifatične karbamatne grupe, ciklične alkilkarbamatne grupe, alkil grupe, trialkilsilil, i grupe koje sadrže tiol.
79.Primena prolinskog analoga formule: gde R21A je grupa Cls alkil; alkoksi; niži tioalkil; halogeno; amino eventualno mono-supstituisana sa Ci_g alkilom; C6, C10 aril, C7-16 aralkil ili Het, pomenuti aril, aralkil ili Het eventualno supstituisan sa R22, gde R22 je Ci_6 alkil, alkoksi, amido, (niži alkil) amid, amino eventualno mono- ili di-supstituisana sa grupom Ci.6 alkil ili Het; a r2ib Je grupa alkil, alkoksi, amino, di(niži alkil)amino, (niži alkil) amid, NO2, OH, halogeno, trifluorometil ili karboksil; za sintezu peptidnog analoga formule I prema zahtevu 29.
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| PCT/CA1999/000736 WO2000009543A2 (en) | 1998-08-10 | 1999-08-09 | Hepatitis c inhibitor tri-peptides |
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| US6608027B1 (en) | 1999-04-06 | 2003-08-19 | Boehringer Ingelheim (Canada) Ltd | Macrocyclic peptides active against the hepatitis C virus |
| UA74546C2 (en) * | 1999-04-06 | 2006-01-16 | Boehringer Ingelheim Ca Ltd | Macrocyclic peptides having activity relative to hepatitis c virus, a pharmaceutical composition and use of the pharmaceutical composition |
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| IL153670A0 (en) | 2000-07-21 | 2003-07-06 | Schering Corp | Novel peptides as ns3-serine protease inhibitors of hepatitis c virus |
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| US6846806B2 (en) | 2000-10-23 | 2005-01-25 | Bristol-Myers Squibb Company | Peptide inhibitors of Hepatitis C virus NS3 protein |
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2000
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- 2000-09-29 US US09/675,398 patent/US6329379B1/en not_active Ceased
- 2000-11-01 US US09/703,751 patent/US6329417B1/en not_active Ceased
-
2001
- 2001-01-22 IL IL141012A patent/IL141012A/en not_active IP Right Cessation
- 2001-02-05 ZA ZA200100971A patent/ZA200100971B/en unknown
- 2001-02-07 IN IN127MU2001 patent/IN2001MU00127A/en unknown
- 2001-02-07 MX MXPA01001423 patent/MX261584B/es active IP Right Grant
- 2001-02-07 MX MXPA06004222 patent/MX257413B/es unknown
- 2001-02-08 BG BG105232A patent/BG65738B1/bg unknown
- 2001-02-09 NO NO20010683A patent/NO328952B1/no not_active IP Right Cessation
- 2001-04-06 US US09/827,976 patent/US6420380B2/en not_active Expired - Lifetime
- 2001-05-04 US US09/849,057 patent/US6410531B1/en not_active Expired - Lifetime
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2002
- 2002-03-05 US US10/091,293 patent/US6534523B1/en not_active Ceased
-
2005
- 2005-09-30 US US11/241,899 patent/USRE40525E1/en not_active Expired - Lifetime
-
2007
- 2007-05-11 IN IN706MU2007 patent/IN2007MU00706A/en unknown
-
2008
- 2008-03-05 US US12/042,627 patent/USRE41894E1/en not_active Expired - Lifetime
- 2008-05-12 US US12/118,926 patent/USRE41356E1/en not_active Expired - Lifetime
- 2008-05-13 US US12/119,609 patent/USRE42164E1/en not_active Expired - Lifetime
- 2008-12-05 AR ARP080105301A patent/AR069583A2/es active IP Right Grant
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2009
- 2009-01-15 IL IL196545A patent/IL196545A/en not_active IP Right Cessation
- 2009-07-23 CY CY20091100795T patent/CY1109291T1/el unknown
- 2009-11-18 JP JP2009262835A patent/JP5021711B2/ja not_active Expired - Lifetime
- 2009-11-27 AR ARP090104583A patent/AR073428A2/es not_active Application Discontinuation
-
2010
- 2010-01-05 NO NO20100004A patent/NO336663B1/no not_active IP Right Cessation
-
2013
- 2013-04-18 CY CY20131100317T patent/CY1113935T1/el unknown
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