GB1358609A - Carboxylic acid derivatives and processes for their p'eparation - Google Patents
Carboxylic acid derivatives and processes for their p'eparationInfo
- Publication number
- GB1358609A GB1358609A GB5300572A GB5300572A GB1358609A GB 1358609 A GB1358609 A GB 1358609A GB 5300572 A GB5300572 A GB 5300572A GB 5300572 A GB5300572 A GB 5300572A GB 1358609 A GB1358609 A GB 1358609A
- Authority
- GB
- United Kingdom
- Prior art keywords
- hydroxy
- give
- formula
- piperidino
- compound
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 238000000034 method Methods 0.000 title abstract 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 6
- 238000006243 chemical reaction Methods 0.000 abstract 5
- -1 3-hydroxypyrrolidino, 3-hydroxy-piperidino, morpholino Chemical group 0.000 abstract 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 abstract 4
- 150000003839 salts Chemical class 0.000 abstract 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 125000004432 carbon atom Chemical group C* 0.000 abstract 3
- 238000005984 hydrogenation reaction Methods 0.000 abstract 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 2
- 229910010082 LiAlH Inorganic materials 0.000 abstract 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 abstract 2
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- 239000002184 metal Chemical class 0.000 abstract 2
- 229910052751 metal Chemical class 0.000 abstract 2
- 150000002989 phenols Chemical class 0.000 abstract 2
- KGKAYWMGPDWLQZ-UHFFFAOYSA-N 1,2-bis(bromomethyl)benzene Chemical compound BrCC1=CC=CC=C1CBr KGKAYWMGPDWLQZ-UHFFFAOYSA-N 0.000 abstract 1
- MVFJGUGAOBQGIA-UHFFFAOYSA-N 1-(2-amino-4-methoxyphenyl)piperidin-3-ol Chemical compound NC1=CC(OC)=CC=C1N1CC(O)CCC1 MVFJGUGAOBQGIA-UHFFFAOYSA-N 0.000 abstract 1
- KCMVRUKJCAZJGL-UHFFFAOYSA-N 1-(2-chloro-4-hydroxyphenyl)piperidin-3-ol Chemical compound ClC=1C=C(C=CC1N1CC(CCC1)O)O KCMVRUKJCAZJGL-UHFFFAOYSA-N 0.000 abstract 1
- LOOGWTWSYCGWEW-UHFFFAOYSA-N 1-(2-chloro-4-methoxyphenyl)piperidin-3-ol Chemical compound ClC=1C=C(C=CC1N1CC(CCC1)O)OC LOOGWTWSYCGWEW-UHFFFAOYSA-N 0.000 abstract 1
- FJWKVPXOBIXXSD-UHFFFAOYSA-N 1-(4-methoxy-2-nitrophenyl)piperidin-3-ol Chemical compound [O-][N+](=O)C1=CC(OC)=CC=C1N1CC(O)CCC1 FJWKVPXOBIXXSD-UHFFFAOYSA-N 0.000 abstract 1
- ALXNEDIWTVDWLG-UHFFFAOYSA-N 1-(4-methoxyphenyl)-3,4-dihydroquinolin-2-one Chemical compound C1=CC(OC)=CC=C1N1C2=CC=CC=C2CCC1=O ALXNEDIWTVDWLG-UHFFFAOYSA-N 0.000 abstract 1
- KCOBIBRGPCFIGF-UHFFFAOYSA-N 1-bromo-4-methoxy-2-nitrobenzene Chemical compound COC1=CC=C(Br)C([N+]([O-])=O)=C1 KCOBIBRGPCFIGF-UHFFFAOYSA-N 0.000 abstract 1
- BAUWRHPMUVYFOD-UHFFFAOYSA-N 1-methylpiperidin-4-ol Chemical compound CN1CCC(O)CC1 BAUWRHPMUVYFOD-UHFFFAOYSA-N 0.000 abstract 1
- HUUPVABNAQUEJW-UHFFFAOYSA-N 1-methylpiperidin-4-one Chemical compound CN1CCC(=O)CC1 HUUPVABNAQUEJW-UHFFFAOYSA-N 0.000 abstract 1
- AOTGWRVCPVLSPA-UHFFFAOYSA-N 2-(4-methoxyanilino)benzoic acid Chemical compound C1=CC(OC)=CC=C1NC1=CC=CC=C1C(O)=O AOTGWRVCPVLSPA-UHFFFAOYSA-N 0.000 abstract 1
- FYDYGTALWXFCDD-UHFFFAOYSA-N 4-(1,2,3,4-tetrahydroquinolin-4-yl)phenol Chemical compound C1=CC(O)=CC=C1C1C2=CC=CC=C2NCC1 FYDYGTALWXFCDD-UHFFFAOYSA-N 0.000 abstract 1
- VJVCPNBCCYHZEW-UHFFFAOYSA-N 4-(1-methyl-3,4-dihydro-2h-quinolin-4-yl)phenol Chemical compound C12=CC=CC=C2N(C)CCC1C1=CC=C(O)C=C1 VJVCPNBCCYHZEW-UHFFFAOYSA-N 0.000 abstract 1
- QPKINSYKYPQLOI-UHFFFAOYSA-N 4-(1-methylpiperidin-4-yl)phenol Chemical compound C1CN(C)CCC1C1=CC=C(O)C=C1 QPKINSYKYPQLOI-UHFFFAOYSA-N 0.000 abstract 1
- NDITXSQXKLJSOP-UHFFFAOYSA-N 4-(4-methoxyphenyl)-1,2,3,4-tetrahydroquinoline Chemical compound C1=CC(OC)=CC=C1C1C2=CC=CC=C2NCC1 NDITXSQXKLJSOP-UHFFFAOYSA-N 0.000 abstract 1
- DMXOCQKOZPIHHR-UHFFFAOYSA-N 4-(4-methoxyphenyl)-1-methyl-3,4-dihydro-2H-quinoline Chemical compound CN1CCC(C2=CC=CC=C12)C1=CC=C(C=C1)OC DMXOCQKOZPIHHR-UHFFFAOYSA-N 0.000 abstract 1
- KZYQKDDDJOFDPC-UHFFFAOYSA-N 4-(4-methoxyphenyl)-3,4-dihydro-1H-quinolin-2-one Chemical compound COC1=CC=C(C=C1)C1CC(NC2=CC=CC=C12)=O KZYQKDDDJOFDPC-UHFFFAOYSA-N 0.000 abstract 1
- XTNFFUNXTVLXSU-UHFFFAOYSA-N 4-hydroxy-1-(4-methoxyphenyl)quinolin-2-one Chemical compound C1=CC(OC)=CC=C1N1C(=O)C=C(O)C2=CC=CC=C21 XTNFFUNXTVLXSU-UHFFFAOYSA-N 0.000 abstract 1
- XAJPURQMMOKCTK-UHFFFAOYSA-N 4-piperidin-1-ylbenzenethiol Chemical compound C1=CC(S)=CC=C1N1CCCCC1 XAJPURQMMOKCTK-UHFFFAOYSA-N 0.000 abstract 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 1
- BISZXDCFQXBVNX-UHFFFAOYSA-N S(=O)(=O)(O)Cl.N1(CCCCC1)C1=CC=CC=C1 Chemical compound S(=O)(=O)(O)Cl.N1(CCCCC1)C1=CC=CC=C1 BISZXDCFQXBVNX-UHFFFAOYSA-N 0.000 abstract 1
- 238000000297 Sandmeyer reaction Methods 0.000 abstract 1
- YVBSAPDHRXHFHV-UHFFFAOYSA-N [chloro(methoxy)methyl]benzene Chemical compound COC(Cl)C1=CC=CC=C1 YVBSAPDHRXHFHV-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical class COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 abstract 1
- 125000004429 atom Chemical group 0.000 abstract 1
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 235000012000 cholesterol Nutrition 0.000 abstract 1
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 abstract 1
- 230000018044 dehydration Effects 0.000 abstract 1
- 238000006297 dehydration reaction Methods 0.000 abstract 1
- 238000006704 dehydrohalogenation reaction Methods 0.000 abstract 1
- 238000006193 diazotization reaction Methods 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 238000011065 in-situ storage Methods 0.000 abstract 1
- QCFRAUYDPLRPCI-UHFFFAOYSA-M magnesium;1-methanidyl-4-methoxybenzene;bromide Chemical compound [Mg+2].[Br-].COC1=CC=C([CH2-])C=C1 QCFRAUYDPLRPCI-UHFFFAOYSA-M 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 230000011987 methylation Effects 0.000 abstract 1
- 238000007069 methylation reaction Methods 0.000 abstract 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 abstract 1
- XURVRZSODRHRNK-UHFFFAOYSA-N o-quinodimethane Chemical group C=C1C=CC=CC1=C XURVRZSODRHRNK-UHFFFAOYSA-N 0.000 abstract 1
- 238000007911 parenteral administration Methods 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 239000000546 pharmaceutical excipient Substances 0.000 abstract 1
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 abstract 1
- BIWOSRSKDCZIFM-UHFFFAOYSA-N piperidin-3-ol Chemical compound OC1CCCNC1 BIWOSRSKDCZIFM-UHFFFAOYSA-N 0.000 abstract 1
- 229920000137 polyphosphoric acid Polymers 0.000 abstract 1
- 238000007363 ring formation reaction Methods 0.000 abstract 1
- 238000007127 saponification reaction Methods 0.000 abstract 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical class C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 abstract 1
- LBUJPTNKIBCYBY-UHFFFAOYSA-N tetrahydroquinoline Natural products C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 abstract 1
- 238000011200 topical administration Methods 0.000 abstract 1
- 230000000699 topical effect Effects 0.000 abstract 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- 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
- C07D207/30—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 two double bonds between ring members or between ring members and non-ring members
- C07D207/32—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 two 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
- C07D207/325—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 two 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 with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
-
- 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
- C07D207/12—Oxygen or sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/20—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms
- C07D211/22—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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
- C07D211/40—Oxygen atoms
- C07D211/42—Oxygen atoms attached in position 3 or 5
-
- 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
- C07D215/04—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 only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms
- C07D215/06—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 only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms having only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached to the ring nitrogen atom
-
- 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
- C07D215/12—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
- C07D215/14—Radicals substituted by oxygen 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
- C07D215/20—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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/096—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Hydrogenated Pyridines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Quinoline Compounds (AREA)
- Pyrrole Compounds (AREA)
- Indole Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2163056A DE2163056A1 (de) | 1971-12-18 | 1971-12-18 | Carbonsaeure-derivate und verfahren zu ihrer herstellung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1358609A true GB1358609A (en) | 1974-07-03 |
Family
ID=5828500
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB5300572A Expired GB1358609A (en) | 1971-12-18 | 1972-11-16 | Carboxylic acid derivatives and processes for their p'eparation |
Country Status (18)
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3448105A (en) * | 1966-06-07 | 1969-06-03 | Sandoz Ag | Basic esters of malonic acid |
| CH514581A (de) * | 1967-02-21 | 1971-10-31 | Sandoz Ag | Verfahren zur Herstellung neuer Essigsäure-Derivate |
| CH526538A (de) * | 1967-07-22 | 1972-08-15 | Merck Patent Gmbh | Verfahren zur Herstellung von Aminophenylessigsäure-Derivaten |
| DE2112272A1 (de) * | 1971-03-15 | 1972-10-05 | Merck Patent Gmbh | Phenoxyessigsaeure-Derivate und Verfahren zu ihrer Herstellung |
-
0
- BE BE792853D patent/BE792853A/xx unknown
-
1971
- 1971-12-18 DE DE2163056A patent/DE2163056A1/de active Pending
-
1972
- 1972-11-14 ZA ZA728065A patent/ZA728065B/xx unknown
- 1972-11-15 IL IL40855A patent/IL40855A/en unknown
- 1972-11-16 GB GB5300572A patent/GB1358609A/en not_active Expired
- 1972-12-05 CS CS8317A patent/CS167366B2/cs unknown
- 1972-12-06 JP JP47121706A patent/JPS4867269A/ja active Pending
- 1972-12-07 FR FR7243549A patent/FR2163487B1/fr not_active Expired
- 1972-12-08 BR BR8702/72A patent/BR7208702D0/pt unknown
- 1972-12-14 AT AT1065772A patent/AT329055B/de not_active IP Right Cessation
- 1972-12-15 NL NL7217100A patent/NL7217100A/xx unknown
- 1972-12-15 DD DD167663A patent/DD105443A5/xx unknown
- 1972-12-15 CA CA158,998A patent/CA980346A/en not_active Expired
- 1972-12-16 PL PL1972159573A patent/PL79179B1/xx unknown
- 1972-12-16 ES ES409727A patent/ES409727A1/es not_active Expired
- 1972-12-18 HU HUME1583A patent/HU165098B/hu unknown
- 1972-12-18 AU AU50227/72A patent/AU464750B2/en not_active Expired
- 1972-12-18 RO RO7200073187A patent/RO62851A/ro unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE2163056A1 (de) | 1973-06-20 |
| DD105443A5 (enrdf_load_stackoverflow) | 1974-04-20 |
| HU165098B (enrdf_load_stackoverflow) | 1974-06-28 |
| IL40855A (en) | 1976-02-29 |
| JPS4867269A (enrdf_load_stackoverflow) | 1973-09-13 |
| FR2163487B1 (enrdf_load_stackoverflow) | 1975-10-17 |
| PL79179B1 (enrdf_load_stackoverflow) | 1975-06-30 |
| ES409727A1 (es) | 1976-03-16 |
| FR2163487A1 (enrdf_load_stackoverflow) | 1973-07-27 |
| AU5022772A (en) | 1974-06-20 |
| AT329055B (de) | 1976-04-26 |
| BE792853A (fr) | 1973-06-15 |
| BR7208702D0 (pt) | 1973-09-20 |
| RO62851A (fr) | 1978-01-15 |
| NL7217100A (enrdf_load_stackoverflow) | 1973-06-20 |
| ATA1065772A (de) | 1975-07-15 |
| CA980346A (en) | 1975-12-23 |
| IL40855A0 (en) | 1973-01-30 |
| CS167366B2 (enrdf_load_stackoverflow) | 1976-04-29 |
| ZA728065B (en) | 1973-07-25 |
| AU464750B2 (en) | 1975-08-20 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Manna et al. | Anti-inflammatory, analgesic and antipyretic 4, 6-disubstituted 3-cyano-2-aminopyridines | |
| SU1232144A3 (ru) | Способ получени карбостирильных производных | |
| US6943196B1 (en) | NF-κB inhibitor comprising phenylmethyl benzoquinone as the active ingredient | |
| DE1468261A1 (de) | Alpha-[Indenyl-(3)]-niedrigalkansaeuren und Verfahren zu ihrer Herstellung | |
| US3712898A (en) | Benzoheterocyclicalkyl derivatives of 4-(2-keto-1-benzimidazolinyl)-piperidine | |
| ES377906A1 (es) | Procedimiento de preparacion de nuevos derivados tricicli- cos. | |
| EP0974583A1 (en) | Phenylpiperidine derivatives | |
| GB2112782A (en) | N-oxide compounds, processes for their manufacture and pharmaceutical compositions containing them | |
| GB1358609A (en) | Carboxylic acid derivatives and processes for their p'eparation | |
| IE31930B1 (en) | New indole derivatives,process for their production and their use | |
| CA1306995C (en) | Cyclic amine and pharmacological composition | |
| AU1572188A (en) | Process for the preparation of quinoline carboxylic acids | |
| US3981877A (en) | Piperidylidene derivatives of carboxy-5H-dibenzo[a,d]cycloheptene | |
| US4442106A (en) | Quinoline derivatives, pharmaceutical compositions containing such compounds, and methods of treating cardiovascular conditions with them | |
| EP0035820B1 (en) | Novel quinoline derivatives, pharmaceutical compositions containing such compounds, and method for the preparation of these compounds | |
| US4029790A (en) | 1-Benzoyl-2 or 4 [2-(4-phenyl-piperazino)-ethyl]-piperidines | |
| DD213921A5 (de) | Verfahren zur herstellung von substituierten nicotinamid 1-oxyd n- und seinen salzen | |
| US5254561A (en) | Tricyclic antipsychotic agents | |
| US3850937A (en) | Derivatives of 6-(gamma-dialkylamino)alkoxy 4,7-dimethoxy benzofuran | |
| US4017624A (en) | N-(ω-Amino)alkylaniline derivatives | |
| US4184040A (en) | Hydroxymethyl-pyridine esters and a process for the preparation thereof | |
| US4473576A (en) | Analgesic 9,9-dimethylbenzomorphanes | |
| US5147882A (en) | Cyclophanes, pharmaceutical compositions containing these compounds and processes for preparing them | |
| US4009275A (en) | Phenoxypropylamine derivatives | |
| US4442107A (en) | Quinoline derivatives, pharmaceutical compositions containing such compounds, and methods for treating cardiovascular conditions with them |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PLNP | Patent lapsed through nonpayment of renewal fees |