HRP20151308T1 - Antibakterijski derivati kinolina - Google Patents
Antibakterijski derivati kinolina Download PDFInfo
- Publication number
- HRP20151308T1 HRP20151308T1 HRP20151308TT HRP20151308T HRP20151308T1 HR P20151308 T1 HRP20151308 T1 HR P20151308T1 HR P20151308T T HRP20151308T T HR P20151308TT HR P20151308 T HRP20151308 T HR P20151308T HR P20151308 T1 HRP20151308 T1 HR P20151308T1
- Authority
- HR
- Croatia
- Prior art keywords
- methyl
- phenyl
- quinolin
- benzyl
- alkyl
- Prior art date
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- 125000002943 quinolinyl group Chemical class N1=C(C=CC2=CC=CC=C12)* 0.000 title claims 2
- 230000000844 anti-bacterial effect Effects 0.000 title 1
- 229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 title 1
- -1 hydroxy, mercapto Chemical group 0.000 claims 18
- 125000000217 alkyl group Chemical group 0.000 claims 13
- 125000004432 carbon atom Chemical group C* 0.000 claims 12
- 125000003118 aryl group Chemical group 0.000 claims 11
- 150000001875 compounds Chemical class 0.000 claims 11
- 229930195734 saturated hydrocarbon Natural products 0.000 claims 10
- 125000005843 halogen group Chemical group 0.000 claims 9
- 125000003545 alkoxy group Chemical group 0.000 claims 7
- 229910052739 hydrogen Inorganic materials 0.000 claims 7
- 239000001257 hydrogen Substances 0.000 claims 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 7
- 125000001424 substituent group Chemical group 0.000 claims 7
- 125000003710 aryl alkyl group Chemical group 0.000 claims 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 5
- 125000004122 cyclic group Chemical group 0.000 claims 4
- 125000001188 haloalkyl group Chemical group 0.000 claims 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 4
- 229910052757 nitrogen Inorganic materials 0.000 claims 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 4
- 125000000815 N-oxide group Chemical group 0.000 claims 3
- 239000002253 acid Substances 0.000 claims 3
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 3
- 125000004414 alkyl thio group Chemical group 0.000 claims 3
- 150000001412 amines Chemical group 0.000 claims 3
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 3
- 125000001246 bromo group Chemical group Br* 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims 3
- 125000004076 pyridyl group Chemical group 0.000 claims 3
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- 208000035143 Bacterial infection Diseases 0.000 claims 2
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims 2
- 208000022362 bacterial infectious disease Diseases 0.000 claims 2
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 2
- 150000002431 hydrogen Chemical group 0.000 claims 2
- 125000002883 imidazolyl group Chemical group 0.000 claims 2
- PKBLLYSFMKAZFL-UHFFFAOYSA-N n'-benzyl-n'-[(6-bromo-2-phenylquinolin-3-yl)-phenylmethyl]-n,n-dimethylethane-1,2-diamine Chemical compound C=1C=CC=CC=1C(C=1C(=NC2=CC=C(Br)C=C2C=1)C=1C=CC=CC=1)N(CCN(C)C)CC1=CC=CC=C1 PKBLLYSFMKAZFL-UHFFFAOYSA-N 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- 125000003373 pyrazinyl group Chemical group 0.000 claims 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims 2
- 125000002098 pyridazinyl group Chemical group 0.000 claims 2
- 125000000168 pyrrolyl group Chemical group 0.000 claims 2
- KZKRRZFCAYOXQE-UHFFFAOYSA-N 1$l^{2}-azinane Chemical group C1CC[N]CC1 KZKRRZFCAYOXQE-UHFFFAOYSA-N 0.000 claims 1
- 125000005943 1,2,3,6-tetrahydropyridyl group Chemical group 0.000 claims 1
- IGGUHKWSTSYJDB-UHFFFAOYSA-N 2-[[(6-bromo-2-methoxyquinolin-3-yl)-phenylmethyl]-(quinolin-5-ylmethyl)amino]-1-(4-methylpiperazin-1-yl)ethanone Chemical compound COC1=NC2=CC=C(Br)C=C2C=C1C(C=1C=CC=CC=1)N(CC=1C2=CC=CN=C2C=CC=1)CC(=O)N1CCN(C)CC1 IGGUHKWSTSYJDB-UHFFFAOYSA-N 0.000 claims 1
- XYLIEXASVAEAQF-UHFFFAOYSA-N 2-[[1-benzofuran-2-yl-(2-phenylquinolin-3-yl)methyl]-benzylamino]-n-methyl-n-propan-2-ylacetamide Chemical compound C=1C2=CC=CC=C2OC=1C(C=1C(=NC2=CC=CC=C2C=1)C=1C=CC=CC=1)N(CC(=O)N(C)C(C)C)CC1=CC=CC=C1 XYLIEXASVAEAQF-UHFFFAOYSA-N 0.000 claims 1
- DLZJLVSPKNSCTJ-UHFFFAOYSA-N 2-[benzyl-[(6-bromo-2-methoxyquinolin-3-yl)-phenylmethyl]amino]-1-(4-methylpiperazin-1-yl)ethanone Chemical compound COC1=NC2=CC=C(Br)C=C2C=C1C(C=1C=CC=CC=1)N(CC=1C=CC=CC=1)CC(=O)N1CCN(C)CC1 DLZJLVSPKNSCTJ-UHFFFAOYSA-N 0.000 claims 1
- QWMZKYBMZBGJJT-UHFFFAOYSA-N 2-[benzyl-[(6-bromo-2-phenylquinolin-3-yl)-phenylmethyl]amino]-n,n-dimethylacetamide Chemical compound C=1C=CC=CC=1C(C=1C(=NC2=CC=C(Br)C=C2C=1)C=1C=CC=CC=1)N(CC(=O)N(C)C)CC1=CC=CC=C1 QWMZKYBMZBGJJT-UHFFFAOYSA-N 0.000 claims 1
- YGBQIWQEHNGZRG-UHFFFAOYSA-N 2-[benzyl-[(6-methyl-2-phenylquinolin-3-yl)-phenylmethyl]amino]-1-(4-benzylpiperazin-1-yl)ethanone Chemical compound C1CN(CC=2C=CC=CC=2)CCN1C(=O)CN(CC=1C=CC=CC=1)C(C=1C=CC=CC=1)C1=CC2=CC(C)=CC=C2N=C1C1=CC=CC=C1 YGBQIWQEHNGZRG-UHFFFAOYSA-N 0.000 claims 1
- OADRDVHVIFIJSP-UHFFFAOYSA-N 2-[benzyl-[(6-methyl-2-phenylquinolin-3-yl)-phenylmethyl]amino]-1-(4-methylpiperazin-1-yl)ethanone Chemical compound C1CN(C)CCN1C(=O)CN(C(C=1C=CC=CC=1)C=1C(=NC2=CC=C(C)C=C2C=1)C=1C=CC=CC=1)CC1=CC=CC=C1 OADRDVHVIFIJSP-UHFFFAOYSA-N 0.000 claims 1
- RVIKGOBHNIAZCT-UHFFFAOYSA-N 2-[benzyl-[(6-methyl-2-phenylquinolin-3-yl)-phenylmethyl]amino]-1-(4-methylpiperidin-1-yl)ethanone Chemical compound C1CC(C)CCN1C(=O)CN(C(C=1C=CC=CC=1)C=1C(=NC2=CC=C(C)C=C2C=1)C=1C=CC=CC=1)CC1=CC=CC=C1 RVIKGOBHNIAZCT-UHFFFAOYSA-N 0.000 claims 1
- RIBMTKLNUUWLIF-UHFFFAOYSA-N 2-[benzyl-[(6-methyl-2-phenylquinolin-3-yl)-phenylmethyl]amino]-1-thiomorpholin-4-ylethanone Chemical compound C1CSCCN1C(=O)CN(CC=1C=CC=CC=1)C(C=1C=CC=CC=1)C1=CC2=CC(C)=CC=C2N=C1C1=CC=CC=C1 RIBMTKLNUUWLIF-UHFFFAOYSA-N 0.000 claims 1
- JNKTVBQEDBSLEL-UHFFFAOYSA-N 2-[benzyl-[(6-methyl-2-phenylquinolin-3-yl)-phenylmethyl]amino]-n,n-diethylacetamide Chemical compound C=1C=CC=CC=1C(C=1C(=NC2=CC=C(C)C=C2C=1)C=1C=CC=CC=1)N(CC(=O)N(CC)CC)CC1=CC=CC=C1 JNKTVBQEDBSLEL-UHFFFAOYSA-N 0.000 claims 1
- SVRPZVCYYRKJEJ-UHFFFAOYSA-N 2-[benzyl-[(6-methyl-2-phenylquinolin-3-yl)-phenylmethyl]amino]-n,n-dimethylacetamide Chemical compound C=1C=CC=CC=1C(C=1C(=NC2=CC=C(C)C=C2C=1)C=1C=CC=CC=1)N(CC(=O)N(C)C)CC1=CC=CC=C1 SVRPZVCYYRKJEJ-UHFFFAOYSA-N 0.000 claims 1
- WZOITQINBOMFAJ-UHFFFAOYSA-N 2-[benzyl-[(6-methyl-2-phenylquinolin-3-yl)-phenylmethyl]amino]-n-(4-methylpiperazin-1-yl)acetamide Chemical compound C1CN(C)CCN1NC(=O)CN(C(C=1C=CC=CC=1)C=1C(=NC2=CC=C(C)C=C2C=1)C=1C=CC=CC=1)CC1=CC=CC=C1 WZOITQINBOMFAJ-UHFFFAOYSA-N 0.000 claims 1
- AHZBZSAMMYRXJZ-UHFFFAOYSA-N 2-[benzyl-[(6-methyl-2-phenylquinolin-3-yl)-phenylmethyl]amino]-n-methyl-n-propan-2-ylacetamide Chemical compound C=1C=CC=CC=1C(C=1C(=NC2=CC=C(C)C=C2C=1)C=1C=CC=CC=1)N(CC(=O)N(C)C(C)C)CC1=CC=CC=C1 AHZBZSAMMYRXJZ-UHFFFAOYSA-N 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
- 239000003242 anti bacterial agent Substances 0.000 claims 1
- 125000004104 aryloxy group Chemical group 0.000 claims 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims 1
- 125000004604 benzisothiazolyl group Chemical group S1N=C(C2=C1C=CC=C2)* 0.000 claims 1
- 125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 claims 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims 1
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims 1
- GLUUGHFHXGJENI-UHFFFAOYSA-N diethylenediamine Natural products C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- AOKZJMMEHIZHBC-UHFFFAOYSA-N ethyl 2-[benzyl-[(6-bromo-2-methoxyquinolin-3-yl)-phenylmethyl]amino]acetate Chemical compound C=1C=CC=CC=1C(C=1C(=NC2=CC=C(Br)C=C2C=1)OC)N(CC(=O)OCC)CC1=CC=CC=C1 AOKZJMMEHIZHBC-UHFFFAOYSA-N 0.000 claims 1
- 125000002541 furyl group Chemical group 0.000 claims 1
- 125000002632 imidazolidinyl group Chemical group 0.000 claims 1
- 125000001041 indolyl group Chemical group 0.000 claims 1
- 125000002346 iodo group Chemical group I* 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 125000001786 isothiazolyl group Chemical group 0.000 claims 1
- 125000000842 isoxazolyl group Chemical group 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000002950 monocyclic group Chemical group 0.000 claims 1
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims 1
- 125000002757 morpholinyl group Chemical group 0.000 claims 1
- BTASAYQHJMELLJ-UHFFFAOYSA-N n'-[(6-bromo-2-methoxyquinolin-3-yl)-phenylmethyl]-n'-(2-methoxyphenyl)-n,n-dimethylethane-1,2-diamine Chemical compound COC1=CC=CC=C1N(CCN(C)C)C(C=1C(=NC2=CC=C(Br)C=C2C=1)OC)C1=CC=CC=C1 BTASAYQHJMELLJ-UHFFFAOYSA-N 0.000 claims 1
- KJXGTIKQXNFZCF-UHFFFAOYSA-N n'-[(6-bromo-2-methoxyquinolin-3-yl)-phenylmethyl]-n,n-dimethyl-n'-phenylethane-1,2-diamine Chemical compound COC1=NC2=CC=C(Br)C=C2C=C1C(C=1C=CC=CC=1)N(CCN(C)C)C1=CC=CC=C1 KJXGTIKQXNFZCF-UHFFFAOYSA-N 0.000 claims 1
- FMVPSNFAXHBKSU-UHFFFAOYSA-N n'-benzyl-n'-[(6-bromo-2-methoxyquinolin-3-yl)-(2-fluorophenyl)methyl]-n,n-dimethylethane-1,2-diamine Chemical compound COC1=NC2=CC=C(Br)C=C2C=C1C(C=1C(=CC=CC=1)F)N(CCN(C)C)CC1=CC=CC=C1 FMVPSNFAXHBKSU-UHFFFAOYSA-N 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- 125000002971 oxazolyl group Chemical group 0.000 claims 1
- 125000004043 oxo group Chemical group O=* 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 125000003386 piperidinyl group Chemical group 0.000 claims 1
- 125000003072 pyrazolidinyl group Chemical group 0.000 claims 1
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 125000001422 pyrrolinyl group Chemical group 0.000 claims 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims 1
- 125000000335 thiazolyl group Chemical group 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
- 125000004306 triazinyl group Chemical group 0.000 claims 1
- 125000001425 triazolyl group Chemical group 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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
- C07D215/20—Oxygen atoms
- C07D215/22—Oxygen atoms attached in position 2 or 4
- C07D215/227—Oxygen atoms attached in position 2 or 4 only one oxygen atom which is attached in position 2
-
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
-
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/4704—2-Quinolinones, e.g. carbostyril
-
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/472—Non-condensed isoquinolines, e.g. papaverine
- A61K31/4725—Non-condensed isoquinolines, e.g. papaverine containing further heterocyclic rings
-
- 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
-
- 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
- A61P31/04—Antibacterial agents
-
- 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
- A61P31/04—Antibacterial agents
- A61P31/06—Antibacterial agents for tuberculosis
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/12—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D401/04—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 directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D401/06—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 carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D401/14—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 three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D405/02—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 two hetero rings
- C07D405/06—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 two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D405/02—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 two hetero rings
- C07D405/12—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 two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
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Claims (11)
1. Spoj prema općoj Formuli (Ia) ili Formuli (Ib):
[image]
[image]
njegova farmaceutski prihvatljiva kisela ili bazična adicijska sol, njegov kvarterni amin, njegov stereokemijski izomerni oblik, njegov tautomerni oblik ili njegov N-oksidni oblik, naznačen time da:
p je cijeli broj jednak nula, 1, 2, 3 ili 4;
q je cijeli broj jednak 1, 2 ili 3;
Z je radikal odabran od formula:
[image]
R1 je cijano, halo, alkil, haloalkil, hidroksi, alkiloksi, alkiltio, alkiloksialkil, alkiltioalkil, arilalkil, di(aril)alkil, aril ili Het;
R2 je vodik, alkiloksi, aril, ariloksi, hidroksi, merkapto, alkiloksialkiloksi, alkiltio, mono ili di(alkil)amino, pirolidino ili radikal s formulom
[image]
pri čemu Y je CH2, O, S, NH ili N-alkil ;
R3 je alkil, arilalkil, aril, mono- ili di-alkilaminoalkil, Het ili Het-alkil;
R4 i R5 svaki neovisno je vodik; alkil; alkiloksialkil; arilalkil; Het-alkil; mono- ili dialkilaminoalkil; Het; ili aril; ili
R4 i R5 zajedno s dušikovim atomom na koji su vezani tvore radikal odabran iz skupine koja sadrži pirolidino, piperidino, piperazino, morfolino, 4-tiomorfolino, 2,3-dihidroizoindol-1-il, tiazolidin-3-il, 1,2,3,6-tetrahidropiridil, 1,4-diazacikloheptil, 1-aza-4-oksacikloheptil, 1,2,3,4-tetrahidroizokinolin-2-il, 2H-pirolil, pirolinil, pirolil, imidazolidinil, pirazolidinil, 2-imidazolinil, 2-pirazolinil, imidazolil, pirazolil, triazolil, piridinil, piridazinil, pirimidinil, pirazinil i triazinil, proizvoljno supstituiran s jednim ili više supstituenata, a svaki supstituent je neovisno odabran od alkila, haloalkila, halo, arilalkila, hidroksi, alkiloksi, amino, mono- ili dialkilamino, alkiltio, alkiloksialkila, alkiltioalkila, arila, piridila ili pirimidinila;
R6 je aril ili Het;
R7 je vodik, halo, alkil, aril ili Het;
R8 je ravni ili razgranati zasićeni radikal ugljikovodika koji ima od 1 do 6 ugljikovih atoma;
R9 je vodik ili alkil;
R10 je okso; i
X je -CH2- ili -CO-;
alkil je ravni ili razgranati zasićeni radikal ugljikovodika koji ima od 1 do 6 ugljikovih atoma; ili je ciklički zasićeni radikal ugljikovodika koji ima od 3 do 6 ugljikovih atoma; ili je ciklički zasićeni radikal ugljikovodika koji ima od 3 do 6 ugljikovih atoma vezanih na ravni ili razgranati zasićeni radikal ugljikovodika koji ima od 1 do 6 ugljikovih atoma; pri čemu svaki ugljikov atom može biti proizvoljno supstituiran s cijano, hidroksi, alkiloksi ili okso;
aril je homocikal odabran od fenila, naftila, acenaftila ili tetrahidronaftila, koji je svaki proizvoljno supstituiran s 1, 2 ili 3 supstituenata, te je svaki supstituent neovisno odabran od hidroksi, halo, cijano, nitro, amino, mono- ili dialkilamino, alkila, haloalkila, alkiloksi, karboksila, alkiloksikarbonila, aminokarbonila, morfolinila ili mono- ili dialkilaminokarbonila;
Het je monociklički heterocikal odabran od N-fenoksipiperidinila, piperidinila, pirolila, pirazolila, imidazolila, furanila, tienila, oksazolila, izoksazolila, tiazolila, izotiazolila, piridinila, pirimidinila, pirazinila ili piridazinila; ili biciklički heterocikal odabran od kinolinila, kinoksalinila, indolila, benzimidazolila, benzoksazolila, benzizoksazolila, benzotiazolila, benzizotiazolila, benzofuranila, benzotienila, 2,3-dihidrobenzo[1,4]dioksinila ili benzo[1,3]dioksolila; svaki monociklički i biciklički heterocikal je proizvoljno supstituiran s 1, 2 ili 3 supstituenata, te je svaki supstituent neovisno odabran od halo, hidroksi, alkila ili alkiloksi;
halo je supstituent odabran od fluoro, kloro, bromo ili jodo; i
haloalkil je ravni ili razgranati zasićeni radikal ugljikovodika koji ima od 1 do 6 ugljikovih atoma ili ciklički zasićeni radikal ugljikovodika koji ima od 3 do 6 ugljikovih atoma ili ciklički zasićeni radikal ugljikovodika koji ima od 3 do 6 ugljikovih atoma vezanih na ravni ili razgranati zasićeni radikal ugljikovodika koji ima od 1 do 6 ugljikovih atoma; pri čemu su jedan ili više ugljikovih atoma supstituirani s jednim ili više halo atoma.
2. Spoj prema zahtjevu 1, naznačen time da
p je 0 ili 1; R1 je halo ili alkil; R2 je alkiloksi ili aril; R3 je aril, arilalkil ili Het-alkil; q je 1; R4 i R5 svaki neovisno su alkil ili R4 i R5zajedno s dušikovim atomom na koji su vezani tvore 4-tiomorfolino, piperidino ili piperazino radikal supstituiran s alkilom ili arilalkilom; R6 je aril proizvoljno supstituiran sa halo, ili R6 je benzofuranil; R7 je vodik; i R8 je ravni ili razgranati zasićeni radikal ugljikovodika koji ima od 1 do 4 ugljikovih atoma.
3. Spoj prema bilo kojem od zahtjeva 1 i 2, naznačen time da
p je 1; Z je radikal s formulom (a); R1 je bromo ili metil; R2 je metiloksi ili fenil; R3 je fenil proizvoljno supstituiran s metiloksi, ili benzilom; q je 1; R4 i R5 su svaki metil, etil ili izopropil, ili R4 i R5 zajedno s dušikovim atomom na koji su vezani tvore 4-tiomorfolino radikal, piperidino radikal supstituiran s metilom na 4-položaju ili piperazino radikal supstituiran s benzilom na 4-položaju; R6 je fenil ili benzofuranil; i R7 je vodik.
4. Spoj prema zahtjevu 2, naznačen time da
p je 0 ili l; R1 je bromo ili metil; R2 je metiloksi ili fenil; R3 je fenil, benzil ili kinolin-5-ilmetil; q je 1; R4 i R5 su svaki metil ili R4 i R5zajedno s dušikovim atomom na koji su vezani tvore piperazino radikal supstituiran s metilom na 4-položaju; R6 je fenil proizvoljno supstituiran s fluoro na 2-položaju; R7 je vodik; i R8 je etil.
5. Spoj naznačen time da je odabran iz skupa koji čine:
2-{benzil-[(6-metil-2-fenil-kinolin-3-il)-fenil-metil]-amino}-N-(4-metil-piperazin-1-il)-acetamid;
N-[(6-bromo-2-metoksi-kinolin-3-il)-fenil-metil]-N',N'-dimetil-N-feniletan-1,2-diamin;
N-benzil-N-[(6-bromo-2-fenil-kinolin-3-il)-fenil-metil]-N',N'-dimetiletan-1,2-diamin;
2- {benzil-[(6-metil-2-fenil-kinolin-3-il)-fenil-metil]-amino}-1-(4-metil-piperazin-1-il)-etanon;
2-{[(6-bromo-2-metoksi-kinolin-3-il)-fenil-metil]-kinolin-5-ilmetilamino}-1-(4-metil-piperazin-1-il)-etanon;
2-{benzil-[(6-bromo-2-metoksi-kinolin-3-il)-fenil-metil]-amino}-1-(4-metil-piperazin-1-il)-etanon;
N-benzil-N-[(6-bromo-2-metoksi-kinolin-3-il)-(2-fluoro-fenil)-metil]-N',N'-dimetil-etan-1,2-diamin;
etil ester {benzil-[(6-bromo-2-metoksi-kinolin-3-il)-fenil-metil]-amino}-octene kiseline; i
2-{benzil-[(6-metil-2-fenil-kinolin-3-il)-fenil-metil]-amino}-1-piperidino-1-il-etanon;
njihova farmaceutski prihvatljiva kisela ili bazična adicijska sol, njihov kvarterni amin, njihov stereokemijski izomerni oblik, njihov tautomerni oblik ili njihov N-oksidni oblik.
6. Spoj naznačen time da je odabran iz skupa koji čine:
2-{benzil-[(6-metil-2-fenil-kinolin-3-il)-fenil-metil]-amino}-1-(4-benzil-piperazin-1-il)-etanon;
N-[(6-bromo-2-metoksi-kinolin-3-il)-fenil-metil]-N-(2-metoksi-fenil)-N',N'-dimetil-etan-1,2-diamin;
2-{benzil-[(6-metil-2-fenil-kinolin-3-il)-fenil-metil]-amino}-N,N-dimetil-acetamid;
N-benzil-N-[(6-bromo-2-fenil-kinolin-3-il)-fenil-metil]-N',N'-dimetiletan-1,2-diamin;
2-{benzil-[(6-metil-2-fenil-kinolin-3-il)-fenil-metil]-amino}-1-(4-metil-piperidin-1-il)-etanon;
2-{benzil-[(6-metil-2-fenil-kinolin-3-il)-fenil-metil]-amino}-N,N-dietil-acetamid;
2-{benzil-[(6-bromo-2-fenil-kinolin-3-il)-fenil-metil]-amino}-N,N-dimetil-acetamid;
2-{[benzofuran-2-il-(2-fenil-kinolin-3-il)-metil]-benzil-amino}-N-izopropil-N-metil-acetamid;
2-{benzil-[(6-metil-2-fenil-kinolin-3-il)-fenil-metil]-amino}-1-tiomorfolin-4-il-etanon; i
2-{benzil-[(6-metil-2-fenil-kinolin-3-il)-fenil-metil]-amino}-N-izopropil-N-metil-acetamid;
njihova farmaceutski prihvatljiva kisela ili bazična adicijska sol, njihov kvarterni amin, njihov stereokemijski izomerni oblik, njihov tautomerni oblik ili njihov N-oksidni oblik.
7. Spoj prema bilo kojem od zahtjeva 1 do 6 naznačen time da je za uporabu kao lijek.
8. Pripravak naznačen time da sadrži farmaceutski prihvatljiv nosač, te kao aktivni sastojak, terapijski učinkovitu količinu spoja kako je definirano u bilo kojem od zahtjeva 1 do 6.
9. Uporaba spoja prema bilo kojem od zahtjeva 1 do 6 ili pripravka prema zahtjevu 8 naznačena time da je za proizvodnju lijeka za liječenje bakterijske bolesti.
10. Spoj prema bilo kojem od zahtjeva 1 do 6 naznačen time da je za uporabu za liječenje bakterijske bolesti.
11. Kombinacija (a) spoja prema bilo kojem od zahtjeva 1 do 6, te (b) jednog ili više drugih antibakterijskih sredstava, naznačena time da je za uporabu kao lijek.
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PCT/EP2006/064656 WO2007014885A1 (en) | 2005-07-28 | 2006-07-26 | Antibacterial quinoline derivatives |
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AU2013254674B2 (en) | 2012-04-27 | 2017-02-02 | Janssen Pharmaceutica Nv | Antibacterial quinoline derivatives |
PL2841426T3 (pl) | 2012-04-27 | 2017-03-31 | Janssen Pharmaceutica N.V. | Przeciwbakteryjne pochodne chinoliny |
ES2596243T3 (es) * | 2012-08-24 | 2017-01-05 | F. Hoffmann-La Roche Ag | Nuevos derivados bicíclicos de piridina |
CN104650054B (zh) * | 2013-11-25 | 2019-09-13 | 重庆医药工业研究院有限责任公司 | 一种抗结核菌的喹啉噻吩芳氧乙胺衍生物 |
CN105175329B (zh) * | 2014-06-10 | 2017-09-19 | 重庆圣华曦药业股份有限公司 | 一种贝达喹啉消旋体的合成路线及方法 |
US20190321324A1 (en) * | 2016-12-30 | 2019-10-24 | Board Of Regents, The University Of Texas System | Quaternary amine antibiotic therapeutics |
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US5235054A (en) * | 1992-07-15 | 1993-08-10 | Pfizer Inc. | 3-carboxaldehyde substituted quinolines and naphthyridines |
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