LT3148B - N-substituted heterocyclic derivatives, their preparation and pharmaceutical compositions containing them - Google Patents
N-substituted heterocyclic derivatives, their preparation and pharmaceutical compositions containing them Download PDFInfo
- Publication number
- LT3148B LT3148B LTIP119A LTIP119A LT3148B LT 3148 B LT3148 B LT 3148B LT IP119 A LTIP119 A LT IP119A LT IP119 A LTIP119 A LT IP119A LT 3148 B LT3148 B LT 3148B
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- Lithuania
- Prior art keywords
- group
- compound
- formula
- substituted
- alkyl
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- 125000000623 heterocyclic group Chemical class 0.000 title claims abstract description 10
- 238000002360 preparation method Methods 0.000 title claims description 7
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 6
- -1 methyltetrazolyl Chemical group 0.000 claims abstract description 47
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 31
- 125000005843 halogen group Chemical group 0.000 claims abstract description 22
- 150000003839 salts Chemical class 0.000 claims abstract description 18
- 239000001257 hydrogen Substances 0.000 claims abstract description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 17
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 12
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 11
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 8
- 150000002431 hydrogen Chemical group 0.000 claims abstract description 8
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 7
- 125000003831 tetrazolyl group Chemical group 0.000 claims abstract description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 6
- 125000004981 cycloalkylmethyl group Chemical group 0.000 claims abstract description 5
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims abstract description 5
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 5
- 125000003884 phenylalkyl group Chemical group 0.000 claims abstract description 5
- 125000006684 polyhaloalkyl group Polymers 0.000 claims abstract description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims abstract description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 3
- 125000001424 substituent group Chemical group 0.000 claims abstract 2
- 150000001875 compounds Chemical class 0.000 claims description 85
- 238000000034 method Methods 0.000 claims description 34
- 150000002148 esters Chemical class 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 11
- 239000004480 active ingredient Substances 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 239000000460 chlorine Substances 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 239000001301 oxygen Substances 0.000 claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 229910052717 sulfur Chemical group 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 4
- 150000001413 amino acids Chemical class 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 125000001188 haloalkyl group Chemical group 0.000 claims description 4
- CFHGBZLNZZVTAY-UHFFFAOYSA-N lawesson's reagent Chemical compound C1=CC(OC)=CC=C1P1(=S)SP(=S)(C=2C=CC(OC)=CC=2)S1 CFHGBZLNZZVTAY-UHFFFAOYSA-N 0.000 claims description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 4
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- RRUDCFGSUDOHDG-UHFFFAOYSA-N acetohydroxamic acid Chemical compound CC(O)=NO RRUDCFGSUDOHDG-UHFFFAOYSA-N 0.000 claims description 3
- 229960001171 acetohydroxamic acid Drugs 0.000 claims description 3
- 150000007513 acids Chemical class 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 239000011593 sulfur Chemical group 0.000 claims description 3
- ZKINQVZUSLLCJY-UHFFFAOYSA-N 2-acetamido-1,3-thiazole-4-carboxylic acid Chemical compound CC(=O)NC1=NC(C(O)=O)=CS1 ZKINQVZUSLLCJY-UHFFFAOYSA-N 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 238000010511 deprotection reaction Methods 0.000 claims description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 2
- HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 claims description 2
- BNZBMEIFAOYZEA-UHFFFAOYSA-N n-cyanoacetamide Chemical compound CC(=O)NC#N BNZBMEIFAOYZEA-UHFFFAOYSA-N 0.000 claims description 2
- UUYJYDILAMMXGM-UHFFFAOYSA-N n-methyl-4-phenylaniline Chemical class C1=CC(NC)=CC=C1C1=CC=CC=C1 UUYJYDILAMMXGM-UHFFFAOYSA-N 0.000 claims description 2
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 239000003204 tranquilizing agent Substances 0.000 claims description 2
- 230000001131 transforming effect Effects 0.000 claims description 2
- 230000036325 urinary excretion Effects 0.000 claims description 2
- DRSHXJFUUPIBHX-UHFFFAOYSA-N COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 Chemical compound COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 DRSHXJFUUPIBHX-UHFFFAOYSA-N 0.000 claims 4
- 229940125904 compound 1 Drugs 0.000 claims 3
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 239000002243 precursor Substances 0.000 claims 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims 1
- 150000007945 N-acyl ureas Chemical class 0.000 claims 1
- 230000002411 adverse Effects 0.000 claims 1
- 239000011575 calcium Substances 0.000 claims 1
- 229910052791 calcium Inorganic materials 0.000 claims 1
- 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 claims 1
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 229940125725 tranquilizer Drugs 0.000 claims 1
- 230000002936 tranquilizing effect Effects 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 abstract description 7
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 3
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 abstract 1
- 229940123413 Angiotensin II antagonist Drugs 0.000 abstract 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 abstract 1
- 239000002333 angiotensin II receptor antagonist Substances 0.000 abstract 1
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 45
- 239000000047 product Substances 0.000 description 36
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 24
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
- 239000000243 solution Substances 0.000 description 20
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
- 239000002244 precipitate Substances 0.000 description 17
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 15
- 238000002844 melting Methods 0.000 description 14
- 230000008018 melting Effects 0.000 description 14
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 13
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 13
- 239000012429 reaction media Substances 0.000 description 13
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
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- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 8
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- 229920006395 saturated elastomer Polymers 0.000 description 7
- CAAMSDWKXXPUJR-UHFFFAOYSA-N 3,5-dihydro-4H-imidazol-4-one Chemical compound O=C1CNC=N1 CAAMSDWKXXPUJR-UHFFFAOYSA-N 0.000 description 6
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- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 6
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
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- 238000011282 treatment Methods 0.000 description 6
- VUZVDXABWUOABD-UHFFFAOYSA-N 2-butyl-5-cyclohexyl-5-methyl-3-[[4-[2-(2h-tetrazol-5-yl)phenyl]phenyl]methyl]imidazol-4-one Chemical compound O=C1N(CC=2C=CC(=CC=2)C=2C(=CC=CC=2)C=2NN=NN=2)C(CCCC)=NC1(C)C1CCCCC1 VUZVDXABWUOABD-UHFFFAOYSA-N 0.000 description 5
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- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 4
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- CUKWUWBLQQDQAC-VEQWQPCFSA-N (3s)-3-amino-4-[[(2s)-1-[[(2s)-1-[[(2s)-1-[[(2s,3s)-1-[[(2s)-1-[(2s)-2-[[(1s)-1-carboxyethyl]carbamoyl]pyrrolidin-1-yl]-3-(1h-imidazol-5-yl)-1-oxopropan-2-yl]amino]-3-methyl-1-oxopentan-2-yl]amino]-3-(4-hydroxyphenyl)-1-oxopropan-2-yl]amino]-3-methyl-1-ox Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](C)C(O)=O)NC(=O)[C@@H](NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@@H](N)CC(O)=O)C(C)C)C1=CC=C(O)C=C1 CUKWUWBLQQDQAC-VEQWQPCFSA-N 0.000 description 3
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- JBWKIWSBJXDJDT-UHFFFAOYSA-N triphenylmethyl chloride Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 JBWKIWSBJXDJDT-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 229960000281 trometamol Drugs 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 229940045860 white wax Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/20—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D239/22—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms directly attached to ring carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A61P27/06—Antiglaucoma agents or miotics
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/70—One oxygen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/84—Sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D403/10—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 carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- 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
- C07D417/02—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 two hetero rings
- C07D417/12—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 two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Ophthalmology & Optometry (AREA)
- Psychiatry (AREA)
- Heart & Thoracic Surgery (AREA)
- Pain & Pain Management (AREA)
- Cardiology (AREA)
- Hospice & Palliative Care (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9111161A FR2681067B1 (fr) | 1991-09-10 | 1991-09-10 | Derives heterocycliques n-substitues, leur preparation, les compositions pharmaceutiques en contenant. |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| LTIP119A LTIP119A (en) | 1994-07-15 |
| LT3148B true LT3148B (en) | 1995-01-31 |
Family
ID=9416798
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| LTIP119A LT3148B (en) | 1991-09-10 | 1992-09-08 | N-substituted heterocyclic derivatives, their preparation and pharmaceutical compositions containing them |
Country Status (19)
| Country | Link |
|---|---|
| EP (1) | EP0532410A1 (en]) |
| JP (1) | JPH05213894A (en]) |
| KR (1) | KR930006008A (en]) |
| AU (1) | AU661017B2 (en]) |
| CA (1) | CA2077967A1 (en]) |
| CZ (1) | CZ275992A3 (en]) |
| FR (1) | FR2681067B1 (en]) |
| HU (1) | HUT63616A (en]) |
| IL (1) | IL103116A (en]) |
| LT (1) | LT3148B (en]) |
| LV (1) | LV10255B (en]) |
| MX (1) | MX9205155A (en]) |
| MY (1) | MY108089A (en]) |
| NO (1) | NO180678C (en]) |
| NZ (1) | NZ244258A (en]) |
| PL (1) | PL171524B1 (en]) |
| RU (1) | RU2107062C1 (en]) |
| TW (1) | TW218871B (en]) |
| ZA (1) | ZA926899B (en]) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2130170T3 (es) * | 1990-12-14 | 1999-07-01 | Smithkline Beecham Corp | Composiciones bloqueantes del receptor de la angiotensina ii. |
| US5484939A (en) * | 1993-03-12 | 1996-01-16 | Lonza Ltd. | 2-substituted 5-chlorimidazoles |
| US5721263A (en) * | 1993-06-07 | 1998-02-24 | Takeda Chemical Industries, Ltd. | Pharmaceutical composition for angiotensin II-mediated diseases |
| HU218680B (hu) * | 1997-07-25 | 2000-10-30 | Sanofi-Synthelabo | Eljárás 1,3-diaza-spiro[4,4]non-1-én-4-on-származékok előállítására és 1-ciano-1-(acil-amino)-ciklopentán intermedierek |
| HU218681B (hu) | 1997-07-25 | 2000-10-30 | Sanofi-Synthelabo | Eljárás 1,3-diaza-spiro(4,4)non-1-én-4-on-származékok előállitására és 1-ciano-1-(acil-amino)-ciklopentán intermedierek |
| NZ508118A (en) | 1998-07-06 | 2003-07-25 | Bristol Myers Squibb Co | Heteroaryl substituted biphenyl sulfonamides useful as dual angiotensin endothelin receptor antogonists |
| US6638937B2 (en) | 1998-07-06 | 2003-10-28 | Bristol-Myers Squibb Co. | Biphenyl sulfonamides as dual angiotensin endothelin receptor antagonists |
| DE19832429A1 (de) * | 1998-07-18 | 2000-01-20 | Hoechst Marion Roussel De Gmbh | Imidazolderivate mit Biphenylsulfonylsubstitution, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament |
| DE19832428A1 (de) * | 1998-07-18 | 2000-01-20 | Hoechst Marion Roussel De Gmbh | Imidazolderivate mit Biphenylsulfonylsubstitution, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament |
| US7091232B2 (en) * | 2002-05-21 | 2006-08-15 | Allergan, Inc. | 4-(substituted cycloalkylmethyl) imidazole-2-thiones, 4-(substituted cycloalkenylmethyl) imidazole-2-thiones, 4-(substituted cycloalkylmethyl) imidazol-2-ones and 4-(substituted cycloalkenylmethyl) imidazol-2-ones and related compounds |
| HRP20050754A2 (en) | 2003-01-31 | 2005-10-31 | Sankyo Company Limited | Medicine for prevention of and treatment for arteriosclerosis and hypertension |
| CA2568640C (en) | 2004-06-04 | 2011-08-09 | Teva Pharmaceutical Industries Ltd. | Pharmaceutical composition containing irbesartan |
| WO2006114707A1 (en) * | 2005-04-28 | 2006-11-02 | Pfizer Limited | Amino acid derivatives |
| US8034782B2 (en) | 2008-07-16 | 2011-10-11 | Synergy Pharmaceuticals, Inc. | Agonists of guanylate cyclase useful for the treatment of gastrointestinal disorders, inflammation, cancer and other disorders |
| US8969514B2 (en) | 2007-06-04 | 2015-03-03 | Synergy Pharmaceuticals, Inc. | Agonists of guanylate cyclase useful for the treatment of hypercholesterolemia, atherosclerosis, coronary heart disease, gallstone, obesity and other cardiovascular diseases |
| ES2393885T7 (es) | 2007-06-04 | 2014-01-30 | Synergy Pharmaceuticals Inc. | Agonistas de la guanilato ciclasa útiles para el tratamiento de trastornos gastrointestinales, inflamación, cáncer y otros trastornos |
| WO2009149279A2 (en) | 2008-06-04 | 2009-12-10 | Synergy Pharmaceuticals Inc. | Agonists of guanylate cyclase useful for the treatment of gastrointestinal disorders, inflammation, cancer and other disorders |
| US9616097B2 (en) | 2010-09-15 | 2017-04-11 | Synergy Pharmaceuticals, Inc. | Formulations of guanylate cyclase C agonists and methods of use |
| JP2016514670A (ja) | 2013-03-15 | 2016-05-23 | シナジー ファーマシューティカルズ インコーポレイテッド | 他の薬物と組み合わせたグアニル酸シクラーゼ受容体アゴニスト |
| CA2905438A1 (en) | 2013-03-15 | 2014-09-25 | Synergy Pharmaceuticals Inc. | Agonists of guanylate cyclase and their uses |
| RS65632B1 (sr) | 2013-06-05 | 2024-07-31 | Bausch Health Ireland Ltd | Ultra-prečišćeni agonisti guanilat-ciklaze c, postupak njihove pripreme i upotrebe |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH540271A (de) | 1970-05-29 | 1973-08-15 | Agripat Sa | Verfahren zur Herstellung neuer, herbizid wirksamer s-Triazine und deren Verwendung zur Bekämpfung von Unkräutern |
| US4017510A (en) | 1975-11-12 | 1977-04-12 | American Cyanamid Company | Imidazoisoindolediones and the use thereof as herbicidal agents |
| EP1447848A2 (en) | 2003-02-14 | 2004-08-18 | Kawasaki Microelectronics, Inc. | Semi conductor integrated circuit including anti-fuse and method for manufacturing the same |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3545597A1 (de) * | 1985-12-21 | 1987-07-02 | Celamerck Gmbh & Co Kg | Neue herbizid wirksame imidazolinone |
| EP0303863A3 (en) * | 1987-08-17 | 1991-10-23 | American Cyanamid Company | Benzenesulfonyl carboxamide compounds, intermediate compounds and methods of preparation thereof and use of said compounds and intermediate compounds as herbicidal agents |
| US4880804A (en) * | 1988-01-07 | 1989-11-14 | E. I. Du Pont De Nemours And Company | Angiotensin II receptor blocking benzimidazoles |
| CA2020073A1 (en) * | 1989-07-03 | 1991-01-04 | Eric E. Allen | Substituted quinazolinones as angiotensin ii antagonists |
| EP0412594B1 (en) * | 1989-07-28 | 1996-01-03 | Merck & Co. Inc. | Substituted triazolinones, triazolinethiones, and triazolinimines as angiotensin II antagonists |
| IL99372A0 (en) * | 1990-09-10 | 1992-08-18 | Ciba Geigy Ag | Azacyclic compounds |
-
1991
- 1991-09-10 FR FR9111161A patent/FR2681067B1/fr not_active Expired - Fee Related
-
1992
- 1992-08-26 TW TW081106738A patent/TW218871B/zh active
- 1992-09-04 LV LVP-92-109A patent/LV10255B/xx unknown
- 1992-09-04 CZ CS922759A patent/CZ275992A3/cs unknown
- 1992-09-04 MY MYPI92001566A patent/MY108089A/en unknown
- 1992-09-08 LT LTIP119A patent/LT3148B/lt not_active IP Right Cessation
- 1992-09-08 NZ NZ244258A patent/NZ244258A/en unknown
- 1992-09-09 EP EP92402459A patent/EP0532410A1/fr not_active Withdrawn
- 1992-09-09 HU HU9202889A patent/HUT63616A/hu unknown
- 1992-09-09 NO NO923509A patent/NO180678C/no unknown
- 1992-09-09 KR KR1019920016618A patent/KR930006008A/ko not_active Ceased
- 1992-09-09 PL PL92295874A patent/PL171524B1/pl unknown
- 1992-09-09 MX MX9205155A patent/MX9205155A/es unknown
- 1992-09-09 IL IL103116A patent/IL103116A/en not_active IP Right Cessation
- 1992-09-09 RU SU5052773A patent/RU2107062C1/ru active
- 1992-09-10 JP JP4242126A patent/JPH05213894A/ja not_active Withdrawn
- 1992-09-10 ZA ZA926899A patent/ZA926899B/xx unknown
- 1992-09-10 CA CA002077967A patent/CA2077967A1/en not_active Abandoned
- 1992-09-10 AU AU22868/92A patent/AU661017B2/en not_active Ceased
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH540271A (de) | 1970-05-29 | 1973-08-15 | Agripat Sa | Verfahren zur Herstellung neuer, herbizid wirksamer s-Triazine und deren Verwendung zur Bekämpfung von Unkräutern |
| US4017510A (en) | 1975-11-12 | 1977-04-12 | American Cyanamid Company | Imidazoisoindolediones and the use thereof as herbicidal agents |
| EP1447848A2 (en) | 2003-02-14 | 2004-08-18 | Kawasaki Microelectronics, Inc. | Semi conductor integrated circuit including anti-fuse and method for manufacturing the same |
Also Published As
| Publication number | Publication date |
|---|---|
| HUT63616A (en) | 1993-09-28 |
| ZA926899B (en) | 1993-03-16 |
| IL103116A (en) | 1998-04-05 |
| NO923509L (no) | 1993-03-11 |
| MX9205155A (es) | 1993-03-01 |
| AU2286892A (en) | 1993-03-11 |
| NZ244258A (en) | 1996-10-28 |
| NO180678C (no) | 1997-05-28 |
| FR2681067A1 (fr) | 1993-03-12 |
| IL103116A0 (en) | 1993-02-21 |
| TW218871B (en]) | 1994-01-11 |
| NO180678B (no) | 1997-02-17 |
| FR2681067B1 (fr) | 1993-12-17 |
| EP0532410A1 (fr) | 1993-03-17 |
| CA2077967A1 (en) | 1993-03-11 |
| MY108089A (en) | 1996-08-15 |
| NO923509D0 (no) | 1992-09-09 |
| KR930006008A (ko) | 1993-04-20 |
| RU2107062C1 (ru) | 1998-03-20 |
| LV10255B (en) | 1995-04-20 |
| JPH05213894A (ja) | 1993-08-24 |
| PL171524B1 (pl) | 1997-05-30 |
| CZ275992A3 (en) | 1993-03-17 |
| LTIP119A (en) | 1994-07-15 |
| LV10255A (lv) | 1994-10-20 |
| AU661017B2 (en) | 1995-07-13 |
| PL295874A1 (en) | 1993-04-19 |
| HU9202889D0 (en) | 1992-11-30 |
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Legal Events
| Date | Code | Title | Description |
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Free format text: 1. JUNGINYS, KURIO FORMULE (I),KURIOJE:- R1 IR R2 YRA PANASUS AR SKIRTINGI, IR KIEKVIENAS NEPRIKLAUSOMAI YRA VANDENILIS ARBA PASIRINKTA GRUPE: ALKILO TARP C1-C6, ALKOKSILO TARP C1-C4, AMINAS, AMINOMETILO, KARBOKSILO, ALKOKSIKARBONILO, KURIOJE ALKOKSIGRUPE YRA TARP C1-C4, CIANAS, TETRAZOLILAS, METILTETRAZOLILAS, METILSULFONILAMINAS, TRIFLUORMETILSULFONILAMINAS, TRIFLUORMETILSULFONILAMINOMETILO GRUPE, N-CIANO ACETAMIDAS, N-HIDROKSIACETAMIDAS, N-(4-KARBOKSI-1,3-TIAZOL-2-IL)ACETAMIDAS, UREIDAS, 2-CIANGUANIDINKARBONILO GRUPE, 2-CIANGUANID |
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Free format text: SANOFI,32-34 RUE MARBEUF, 75008 PARIS,FR,19971113 |
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Effective date: 19980908 |