LT3958B - Process for preparing hypoglycemic guanidine derivatives - Google Patents
Process for preparing hypoglycemic guanidine derivatives Download PDFInfo
- Publication number
- LT3958B LT3958B LTIP1646A LTIP1646A LT3958B LT 3958 B LT3958 B LT 3958B LT IP1646 A LTIP1646 A LT IP1646A LT IP1646 A LTIP1646 A LT IP1646A LT 3958 B LT3958 B LT 3958B
- Authority
- LT
- Lithuania
- Prior art keywords
- morpholinophenyl
- formula
- hours
- methyl
- compounds
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title claims 2
- 230000002218 hypoglycaemic effect Effects 0.000 title description 5
- 150000002357 guanidines Chemical class 0.000 title 1
- 229940083094 guanine derivative acting on arteriolar smooth muscle Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 39
- 150000003839 salts Chemical class 0.000 claims abstract description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 51
- -1 N-ethylamino Chemical group 0.000 claims description 18
- 238000010992 reflux Methods 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 6
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- PLYTVAFAKDFFKM-UHFFFAOYSA-N 3,4-dimethylmorpholine Chemical compound CC1COCCN1C PLYTVAFAKDFFKM-UHFFFAOYSA-N 0.000 claims description 2
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 2
- 239000011541 reaction mixture Substances 0.000 claims description 2
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims description 2
- KOHBEDRJXKOYHL-UHFFFAOYSA-N 2-methoxy-n-methylethanamine Chemical compound CNCCOC KOHBEDRJXKOYHL-UHFFFAOYSA-N 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract description 2
- 229940126904 hypoglycaemic agent Drugs 0.000 abstract description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 3
- 125000001931 aliphatic group Chemical group 0.000 abstract 3
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 3
- 125000000623 heterocyclic group Chemical group 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 1
- 125000004644 alkyl sulfinyl group Chemical group 0.000 abstract 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 abstract 1
- 125000004414 alkyl thio group Chemical group 0.000 abstract 1
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 125000000547 substituted alkyl group Chemical group 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 33
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 239000000203 mixture Substances 0.000 description 20
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 15
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 14
- 239000000243 solution Substances 0.000 description 13
- 238000000034 method Methods 0.000 description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000008103 glucose Substances 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- AQYPBQKDGHHKBD-UHFFFAOYSA-N (2-morpholin-4-ylphenyl)cyanamide Chemical compound N#CNC1=CC=CC=C1N1CCOCC1 AQYPBQKDGHHKBD-UHFFFAOYSA-N 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
- KQNKJJBFUFKYFX-UHFFFAOYSA-N acetic acid;trihydrate Chemical compound O.O.O.CC(O)=O KQNKJJBFUFKYFX-UHFFFAOYSA-N 0.000 description 5
- 229940046892 lead acetate Drugs 0.000 description 5
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 229910021529 ammonia Inorganic materials 0.000 description 4
- 239000012267 brine Substances 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 235000019198 oils Nutrition 0.000 description 4
- 239000008194 pharmaceutical composition Substances 0.000 description 4
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 description 4
- 238000003556 assay Methods 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- CMMLLKHOSNEVFO-UHFFFAOYSA-N (2-morpholin-4-ylphenyl)thiourea Chemical compound NC(=S)NC1=CC=CC=C1N1CCOCC1 CMMLLKHOSNEVFO-UHFFFAOYSA-N 0.000 description 2
- LOPWBKHHJFJKPO-UHFFFAOYSA-N (3-methyl-2-morpholin-4-ylphenyl)cyanamide Chemical compound CC1=CC=CC(NC#N)=C1N1CCOCC1 LOPWBKHHJFJKPO-UHFFFAOYSA-N 0.000 description 2
- VGICPVCQAZPROO-UHFFFAOYSA-N (3-methyl-2-morpholin-4-ylphenyl)thiourea Chemical compound CC1=CC=CC(NC(N)=S)=C1N1CCOCC1 VGICPVCQAZPROO-UHFFFAOYSA-N 0.000 description 2
- AHVKUQNZOIILGF-UHFFFAOYSA-N (4-methoxy-2-morpholin-4-ylphenyl)cyanamide Chemical compound COC1=CC=C(NC#N)C(N2CCOCC2)=C1 AHVKUQNZOIILGF-UHFFFAOYSA-N 0.000 description 2
- LGVPAWVLLZMLPB-UHFFFAOYSA-N (4-methoxy-2-morpholin-4-ylphenyl)thiourea Chemical compound COC1=CC=C(NC(N)=S)C(N2CCOCC2)=C1 LGVPAWVLLZMLPB-UHFFFAOYSA-N 0.000 description 2
- KUYYWVDLLLFAAA-UHFFFAOYSA-N (5-chloro-2-morpholin-4-ylphenyl)cyanamide Chemical compound N#CNC1=CC(Cl)=CC=C1N1CCOCC1 KUYYWVDLLLFAAA-UHFFFAOYSA-N 0.000 description 2
- FDOGAHCLAIGGEZ-UHFFFAOYSA-N (5-chloro-2-morpholin-4-ylphenyl)thiourea Chemical compound NC(=S)NC1=CC(Cl)=CC=C1N1CCOCC1 FDOGAHCLAIGGEZ-UHFFFAOYSA-N 0.000 description 2
- YIMGGHGOVMBIJO-UHFFFAOYSA-N 1,1-dimethyl-2-(2-morpholin-4-ylphenyl)guanidine Chemical compound CN(C)C(N)=NC1=CC=CC=C1N1CCOCC1 YIMGGHGOVMBIJO-UHFFFAOYSA-N 0.000 description 2
- ZTNWZRBNTYKWHF-UHFFFAOYSA-N 2-(5-fluoro-2-morpholin-4-ylphenyl)-1,1-dimethylguanidine Chemical compound CN(C)C(N)=NC1=CC(F)=CC=C1N1CCOCC1 ZTNWZRBNTYKWHF-UHFFFAOYSA-N 0.000 description 2
- OKTXVZOPNMPSAU-UHFFFAOYSA-N 4-(2-isothiocyanato-5-methoxyphenyl)morpholine Chemical compound COC1=CC=C(N=C=S)C(N2CCOCC2)=C1 OKTXVZOPNMPSAU-UHFFFAOYSA-N 0.000 description 2
- GYILGUCNWIUUOX-UHFFFAOYSA-N 4-(2-isothiocyanato-6-methylphenyl)morpholine Chemical compound CC1=CC=CC(N=C=S)=C1N1CCOCC1 GYILGUCNWIUUOX-UHFFFAOYSA-N 0.000 description 2
- OFWPPBDBRPIZRT-UHFFFAOYSA-N 4-(4-chloro-2-isothiocyanatophenyl)morpholine Chemical compound S=C=NC1=CC(Cl)=CC=C1N1CCOCC1 OFWPPBDBRPIZRT-UHFFFAOYSA-N 0.000 description 2
- 229920001817 Agar Polymers 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 239000008272 agar Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 206010012601 diabetes mellitus Diseases 0.000 description 2
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 150000002332 glycine derivatives Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000012047 saturated solution Substances 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 150000003585 thioureas Chemical class 0.000 description 2
- DYMVJWOTOQCATD-UHFFFAOYSA-N (5-fluoro-2-morpholin-4-ylphenyl)cyanamide Chemical compound N#CNC1=CC(F)=CC=C1N1CCOCC1 DYMVJWOTOQCATD-UHFFFAOYSA-N 0.000 description 1
- SOWKCCAHSVVGPU-UHFFFAOYSA-N (5-fluoro-2-morpholin-4-ylphenyl)thiourea Chemical compound NC(=S)NC1=CC(F)=CC=C1N1CCOCC1 SOWKCCAHSVVGPU-UHFFFAOYSA-N 0.000 description 1
- BRKNKZKJTGFCIB-UHFFFAOYSA-N 1,1-dimethyl-2-(3-methyl-2-morpholin-4-ylphenyl)guanidine Chemical compound CN(C)C(N)=NC1=CC=CC(C)=C1N1CCOCC1 BRKNKZKJTGFCIB-UHFFFAOYSA-N 0.000 description 1
- OZTPZKOTNKOWFT-UHFFFAOYSA-N 1,1-dimethyl-2-[5-(2-methylpropyl)-2-morpholin-4-ylphenyl]guanidine Chemical compound CN(C)C(N)=NC1=CC(CC(C)C)=CC=C1N1CCOCC1 OZTPZKOTNKOWFT-UHFFFAOYSA-N 0.000 description 1
- GJWWEGYULZSQLT-UHFFFAOYSA-N 1-(2-methoxyethyl)-1-methyl-2-(2-morpholin-4-ylphenyl)guanidine Chemical compound COCCN(C)C(N)=NC1=CC=CC=C1N1CCOCC1 GJWWEGYULZSQLT-UHFFFAOYSA-N 0.000 description 1
- WJPCLVRIKPPQNQ-UHFFFAOYSA-N 1-ethyl-1-(2-methoxyethyl)-2-(2-morpholin-4-ylphenyl)guanidine Chemical compound COCCN(CC)C(N)=NC1=CC=CC=C1N1CCOCC1 WJPCLVRIKPPQNQ-UHFFFAOYSA-N 0.000 description 1
- FGFWHCOPGCHCKF-UHFFFAOYSA-N 1-ethyl-1-methyl-2-(2-morpholin-4-ylphenyl)guanidine Chemical compound CCN(C)C(N)=NC1=CC=CC=C1N1CCOCC1 FGFWHCOPGCHCKF-UHFFFAOYSA-N 0.000 description 1
- ZWXTUKIOAVCZIO-UHFFFAOYSA-N 1-methyl-1-(2-methylsulfanylethyl)-2-(2-morpholin-4-ylphenyl)guanidine Chemical compound CSCCN(C)C(N)=NC1=CC=CC=C1N1CCOCC1 ZWXTUKIOAVCZIO-UHFFFAOYSA-N 0.000 description 1
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 1
- WFDMHFWYPBYQMA-UHFFFAOYSA-N 2,6-dimethyl-n'-(2-morpholin-4-ylphenyl)morpholine-4-carboximidamide Chemical compound C1C(C)OC(C)CN1C(=N)NC1=CC=CC=C1N1CCOCC1 WFDMHFWYPBYQMA-UHFFFAOYSA-N 0.000 description 1
- VFQRQOCAKNYDLF-UHFFFAOYSA-N 2-(4-methoxy-2-morpholin-4-ylphenyl)-1,1-dimethylguanidine Chemical compound COC1=CC=C(N=C(N)N(C)C)C(N2CCOCC2)=C1 VFQRQOCAKNYDLF-UHFFFAOYSA-N 0.000 description 1
- FQSYRJIMZVMLBM-UHFFFAOYSA-N 2-(5-chloro-2-morpholin-4-ylphenyl)-1,1-dimethylguanidine Chemical compound CN(C)C(N)=NC1=CC(Cl)=CC=C1N1CCOCC1 FQSYRJIMZVMLBM-UHFFFAOYSA-N 0.000 description 1
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- 150000002823 nitrates Chemical class 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- UKLNMMHNWFDKNT-UHFFFAOYSA-M sodium chlorite Chemical compound [Na+].[O-]Cl=O UKLNMMHNWFDKNT-UHFFFAOYSA-M 0.000 description 1
- 229960002218 sodium chlorite Drugs 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003890 succinate salts Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- 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
- C07D295/12—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 or doubly bound nitrogen atoms
- C07D295/135—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 or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C257/00—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines
- C07C257/10—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. amidines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
- C07C279/18—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to carbon atoms of six-membered aromatic rings
-
- 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
- C07D207/18—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 one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—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 one double bond between ring members or between a ring member and a non-ring member 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
-
- 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
- C07D211/68—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 one double bond between ring members or between a ring member and a non-ring member
- C07D211/72—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 one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
- C07D223/02—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D223/06—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings 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
- C07D223/12—Nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D225/00—Heterocyclic compounds containing rings of more than seven members having one nitrogen atom as the only ring hetero atom
- C07D225/04—Heterocyclic compounds containing rings of more than seven members having one nitrogen atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
-
- 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
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
- C07D233/44—Nitrogen atoms not forming part of a nitro radical
- C07D233/50—Nitrogen atoms not forming part of a nitro radical with carbocyclic radicals directly attached to said nitrogen atoms
-
- 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
- C07D295/12—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 or doubly bound nitrogen atoms
- C07D295/125—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 or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/13—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 or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Diabetes (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Endocrinology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Emergency Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Saccharide Compounds (AREA)
- Steroid Compounds (AREA)
- Indole Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Thermotherapy And Cooling Therapy Devices (AREA)
- Soy Sauces And Products Related Thereto (AREA)
- Investigating Or Analysing Materials By Optical Means (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB898903592A GB8903592D0 (en) | 1989-02-16 | 1989-02-16 | Therapeutic agents |
Publications (2)
Publication Number | Publication Date |
---|---|
LTIP1646A LTIP1646A (en) | 1995-07-25 |
LT3958B true LT3958B (en) | 1996-05-27 |
Family
ID=10651840
Family Applications (3)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
LTIP1648A LT3961B (en) | 1989-02-16 | 1993-12-21 | Hypoglycemic compounds, process for preparing thereof and pharmaceutical compositions containing them |
LTIP1646A LT3958B (en) | 1989-02-16 | 1993-12-21 | Process for preparing hypoglycemic guanidine derivatives |
LTIP1647A LT3960B (en) | 1989-02-16 | 1993-12-21 | Process for preparing hypoglycemic compounds |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
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LTIP1648A LT3961B (en) | 1989-02-16 | 1993-12-21 | Hypoglycemic compounds, process for preparing thereof and pharmaceutical compositions containing them |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
LTIP1647A LT3960B (en) | 1989-02-16 | 1993-12-21 | Process for preparing hypoglycemic compounds |
Country Status (26)
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US (2) | US5223498A (no) |
EP (1) | EP0385038B1 (no) |
JP (1) | JP2545475B2 (no) |
AT (1) | ATE90074T1 (no) |
BG (1) | BG60557B1 (no) |
CS (1) | CS277609B6 (no) |
DD (1) | DD294023A5 (no) |
DE (1) | DE68906880T2 (no) |
DK (1) | DK640889A (no) |
ES (1) | ES2055115T3 (no) |
FI (1) | FI95565C (no) |
GB (1) | GB8903592D0 (no) |
GE (1) | GEP19981040B (no) |
HU (1) | HU211571A9 (no) |
IL (1) | IL92963A (no) |
LT (3) | LT3961B (no) |
LV (1) | LV10619B (no) |
MY (1) | MY105052A (no) |
NO (1) | NO177993C (no) |
PL (2) | PL161961B1 (no) |
PT (1) | PT92770B (no) |
RO (2) | RO107945B1 (no) |
RU (3) | RU1826969C (no) |
UA (2) | UA27713C2 (no) |
YU (1) | YU48164B (no) |
ZA (1) | ZA899941B (no) |
Families Citing this family (13)
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DE3766696D1 (de) * | 1986-12-27 | 1991-01-24 | Konishiroku Photo Ind | Lichtempfindliches photographisches silberhalogenidmaterial. |
IN172842B (no) * | 1990-05-17 | 1993-12-11 | Boots Pharmaceuticals Limited | |
GB9418912D0 (en) * | 1994-09-20 | 1994-11-09 | Fisons Corp | Pharmaceutically active compounds |
AU4176396A (en) * | 1994-12-08 | 1996-06-26 | Knoll Aktiengesellschaft | Use of substituted phenylamidine and phenylguanidine compounds for the treatment of cerebral and cardiac ischaemia, convulsion and sickle cell anaemia |
TW397812B (en) * | 1995-02-11 | 2000-07-11 | Astra Ab | Bicyclic isothiourea derivatives useful in therapy |
AU2978197A (en) * | 1996-06-04 | 1998-01-05 | Chugai Seiyaku Kabushiki Kaisha | Substituted benzenes having nos inhibitory effects |
US6756389B2 (en) * | 1996-08-09 | 2004-06-29 | Cambridge Neuroscience, Inc. | Pharmaceutically active compounds and methods of use |
US6187203B1 (en) * | 1998-12-01 | 2001-02-13 | Academia Sinica | Sample purification apparatus and method |
WO2001047888A1 (fr) * | 1999-12-28 | 2001-07-05 | Nissan Chemical Industries, Ltd. | Composes imino heterocycliques, fongicides et insecticides a usage agricole et horticole |
IL149357A0 (en) * | 2000-09-07 | 2002-11-10 | Bayer Ag | Cyclic and acyclic amidines and pharmaceutical compositions containing them for use as progesterone receptor binding agents |
PE20070404A1 (es) * | 2005-07-29 | 2007-05-10 | Wyeth Corp | Compuestos derivados de cianopirrol-sulfonamida como moduladores del receptor de progesterona |
PE20070341A1 (es) * | 2005-07-29 | 2007-04-13 | Wyeth Corp | Derivados de pirrol como moduladores del receptor de progesterona |
PE20070182A1 (es) * | 2005-07-29 | 2007-03-06 | Wyeth Corp | Derivados cianopirrol-fenil amida como moduladores del receptor de progesterona |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
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US77978A (en) | 1868-05-19 | Improvement in low-water indicators |
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1989
- 1989-02-16 GB GB898903592A patent/GB8903592D0/en active Pending
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- 1989-12-28 DE DE8989313636T patent/DE68906880T2/de not_active Expired - Fee Related
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- 1989-12-29 PT PT92770A patent/PT92770B/pt not_active IP Right Cessation
- 1989-12-30 RO RO147103A patent/RO107945B1/ro unknown
- 1989-12-30 RO RO143555A patent/RO105807B1/ro unknown
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1990
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- 1990-12-03 RU SU904831862A patent/RU1797610C/ru active
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1992
- 1992-02-27 RU SU925011043A patent/RU2052452C1/ru active
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1993
- 1993-01-27 US US08/009,807 patent/US5373008A/en not_active Expired - Fee Related
- 1993-06-30 LV LVP-93-815A patent/LV10619B/en unknown
- 1993-12-21 LT LTIP1648A patent/LT3961B/lt not_active IP Right Cessation
- 1993-12-21 LT LTIP1646A patent/LT3958B/lt not_active IP Right Cessation
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1994
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1995
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