DD282457A5 - Verfahren zur herstellung neuer heterocyclischer derivate - Google Patents
Verfahren zur herstellung neuer heterocyclischer derivate Download PDFInfo
- Publication number
- DD282457A5 DD282457A5 DD88319829A DD31982988A DD282457A5 DD 282457 A5 DD282457 A5 DD 282457A5 DD 88319829 A DD88319829 A DD 88319829A DD 31982988 A DD31982988 A DD 31982988A DD 282457 A5 DD282457 A5 DD 282457A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- hydrogen
- compound
- formula
- hydrogen atom
- acid
- Prior art date
Links
- 238000000034 method Methods 0.000 title description 37
- 238000002360 preparation method Methods 0.000 title description 12
- 230000008569 process Effects 0.000 title description 7
- 150000001875 compounds Chemical class 0.000 claims description 67
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 33
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- 239000001257 hydrogen Substances 0.000 claims description 20
- 239000002904 solvent Substances 0.000 claims description 17
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 16
- 239000002253 acid Substances 0.000 claims description 15
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 13
- 238000006243 chemical reaction Methods 0.000 claims description 11
- 150000002431 hydrogen Chemical class 0.000 claims description 11
- 239000003054 catalyst Substances 0.000 claims description 10
- 239000012442 inert solvent Substances 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 150000007513 acids Chemical class 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 4
- 229910052763 palladium Inorganic materials 0.000 claims description 4
- 125000006239 protecting group Chemical group 0.000 claims description 4
- 150000003230 pyrimidines Chemical class 0.000 claims description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 3
- 239000007868 Raney catalyst Substances 0.000 claims description 3
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims description 3
- 229910000564 Raney nickel Inorganic materials 0.000 claims description 3
- 239000000852 hydrogen donor Substances 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- OQLZINXFSUDMHM-UHFFFAOYSA-N Acetamidine Chemical compound CC(N)=N OQLZINXFSUDMHM-UHFFFAOYSA-N 0.000 claims description 2
- PNKUSGQVOMIXLU-UHFFFAOYSA-N Formamidine Chemical compound NC=N PNKUSGQVOMIXLU-UHFFFAOYSA-N 0.000 claims description 2
- 150000001298 alcohols Chemical class 0.000 claims description 2
- 238000009835 boiling Methods 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 2
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 2
- 150000004985 diamines Chemical class 0.000 claims description 2
- 238000005984 hydrogenation reaction Methods 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims 1
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 1
- 229940100198 alkylating agent Drugs 0.000 claims 1
- 239000002168 alkylating agent Substances 0.000 claims 1
- 125000005263 alkylenediamine group Chemical group 0.000 claims 1
- 239000013067 intermediate product Substances 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound 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 claims 1
- 230000000694 effects Effects 0.000 abstract description 7
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- 125000000623 heterocyclic group Chemical group 0.000 abstract description 4
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- 210000000349 chromosome Anatomy 0.000 abstract 1
- 229940126601 medicinal product Drugs 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 37
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 33
- 239000000203 mixture Substances 0.000 description 32
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 27
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- 238000004458 analytical method Methods 0.000 description 24
- 239000000243 solution Substances 0.000 description 21
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 20
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
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- -1 mercapto, thiomethyl Chemical group 0.000 description 15
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- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 8
- 229910052736 halogen Inorganic materials 0.000 description 8
- 150000002367 halogens Chemical class 0.000 description 8
- 239000000543 intermediate Substances 0.000 description 8
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 238000004440 column chromatography Methods 0.000 description 6
- 235000019253 formic acid Nutrition 0.000 description 6
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical group COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 5
- 102000014415 Muscarinic acetylcholine receptor Human genes 0.000 description 5
- 108050003473 Muscarinic acetylcholine receptor Proteins 0.000 description 5
- 239000013543 active substance Substances 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 238000010494 dissociation reaction Methods 0.000 description 5
- 230000005593 dissociations Effects 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 5
- 229940013688 formic acid Drugs 0.000 description 5
- 150000003254 radicals Chemical class 0.000 description 5
- 229910000104 sodium hydride Inorganic materials 0.000 description 5
- SJSRFXJWBKOROD-UHFFFAOYSA-N 1,1'-bi(cyclohexyl)-1-carboxylic acid Chemical compound C1CCCCC1C1(C(=O)O)CCCCC1 SJSRFXJWBKOROD-UHFFFAOYSA-N 0.000 description 4
- UFQDKRWQSFLPQY-UHFFFAOYSA-N 4,5-dihydro-1h-imidazol-3-ium;chloride Chemical compound Cl.C1CN=CN1 UFQDKRWQSFLPQY-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 4
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
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- 238000010521 absorption reaction Methods 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 4
- 239000005557 antagonist Substances 0.000 description 4
- NZUPCNDJBJXXRF-UHFFFAOYSA-O bethanechol Chemical compound C[N+](C)(C)CC(C)OC(N)=O NZUPCNDJBJXXRF-UHFFFAOYSA-O 0.000 description 4
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- 235000019359 magnesium stearate Nutrition 0.000 description 4
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- 230000000144 pharmacologic effect Effects 0.000 description 4
- 239000012312 sodium hydride Substances 0.000 description 4
- 239000000829 suppository Substances 0.000 description 4
- 238000001665 trituration Methods 0.000 description 4
- 125000004864 4-thiomethylphenyl group Chemical group 0.000 description 3
- 229920002261 Corn starch Polymers 0.000 description 3
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 3
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 229930195725 Mannitol Natural products 0.000 description 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
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- HHJDQGGPNCDHDP-UHFFFAOYSA-N (2-methylpyrimidin-5-yl) 1-cyclohexylcyclohexane-1-carboxylate Chemical compound C1=NC(C)=NC=C1OC(=O)C1(C2CCCCC2)CCCCC1 HHJDQGGPNCDHDP-UHFFFAOYSA-N 0.000 description 2
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- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
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- YTRNSQPXEDGWMR-UHFFFAOYSA-N alpha-Cyclohexylmandelic acid Chemical compound C=1C=CC=CC=1C(O)(C(=O)O)C1CCCCC1 YTRNSQPXEDGWMR-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
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- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
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- WZHCOOQXZCIUNC-UHFFFAOYSA-N cyclandelate Chemical compound C1C(C)(C)CC(C)CC1OC(=O)C(O)C1=CC=CC=C1 WZHCOOQXZCIUNC-UHFFFAOYSA-N 0.000 description 2
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- AOSZTAHDEDLTLQ-AZKQZHLXSA-N (1S,2S,4R,8S,9S,11S,12R,13S,19S)-6-[(3-chlorophenyl)methyl]-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one Chemical compound C([C@@H]1C[C@H]2[C@H]3[C@]([C@]4(C=CC(=O)C=C4[C@@H](F)C3)C)(F)[C@@H](O)C[C@@]2([C@@]1(C1)C(=O)CO)C)N1CC1=CC=CC(Cl)=C1 AOSZTAHDEDLTLQ-AZKQZHLXSA-N 0.000 description 1
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- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 229940050176 methyl chloride Drugs 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000003149 muscarinic antagonist Substances 0.000 description 1
- DFCDLLNULGMFAS-UHFFFAOYSA-N n'-tritylethane-1,2-diamine Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(NCCN)C1=CC=CC=C1 DFCDLLNULGMFAS-UHFFFAOYSA-N 0.000 description 1
- PTYIVRDPUKLIQP-UHFFFAOYSA-N n-(5-hydroxy-1,4,5,6-tetrahydropyrimidin-2-yl)nitramide Chemical compound OC1CNC(N[N+]([O-])=O)=NC1 PTYIVRDPUKLIQP-UHFFFAOYSA-N 0.000 description 1
- 229940074355 nitric acid Drugs 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000002687 nonaqueous vehicle Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 229940098462 oral drops Drugs 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 208000011906 peptic ulcer disease Diseases 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 206010037628 pylorospasm Diseases 0.000 description 1
- 238000005956 quaternization reaction Methods 0.000 description 1
- 238000000611 regression analysis Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000007873 sieving Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000003506 spasmogen Substances 0.000 description 1
- 208000018198 spasticity Diseases 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229940032330 sulfuric acid Drugs 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000035900 sweating Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 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
- 230000002485 urinary effect Effects 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 210000001835 viscera Anatomy 0.000 description 1
- 239000008215 water for injection Substances 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
- C07D239/06—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/10—Laxatives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/12—Antidiarrhoeals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D233/48—Nitrogen atoms not forming part of a nitro radical with acyclic hydrocarbon or substituted acyclic hydrocarbon radicals, attached to said nitrogen atoms
-
- 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
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT8721976A IT1231237B (it) | 1987-09-21 | 1987-09-21 | Derivati eterociclici |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD282457A5 true DD282457A5 (de) | 1990-09-12 |
Family
ID=11189654
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD88319829A DD282457A5 (de) | 1987-09-21 | 1988-09-15 | Verfahren zur herstellung neuer heterocyclischer derivate |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US4973592A (fr) |
| EP (1) | EP0309425A3 (fr) |
| JP (1) | JPH01128970A (fr) |
| KR (1) | KR890005063A (fr) |
| AU (1) | AU2237788A (fr) |
| DD (1) | DD282457A5 (fr) |
| DK (1) | DK522888A (fr) |
| FI (1) | FI884303A7 (fr) |
| HU (1) | HUT56553A (fr) |
| IT (1) | IT1231237B (fr) |
| NO (1) | NO884175L (fr) |
| PL (5) | PL274750A1 (fr) |
| PT (2) | PT88542A (fr) |
| SU (1) | SU1676446A3 (fr) |
| YU (1) | YU177288A (fr) |
| ZA (1) | ZA887002B (fr) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4983604A (en) * | 1987-11-13 | 1991-01-08 | The Rockefeller University | Inhibitors of nonenzymatic cross-linking |
| CA2027530C (fr) * | 1989-10-20 | 2001-05-08 | Jules Freedman | Composes w-phenoxy-heterocycliques |
| DE4142190A1 (de) * | 1991-12-20 | 1993-06-24 | Bayer Ag | Verfahren zur herstellung von optisch aktiven (alpha)-hydroxycarbonsaeuren |
| ZA931109B (en) * | 1992-03-04 | 1993-09-22 | Akzo Nv | Tetrahydropyrimidine derivatives. |
| USRE38952E1 (en) | 1994-03-08 | 2006-01-31 | Hale Nathan S | Heat activated ink jet ink |
| WO1999014200A1 (fr) * | 1997-09-18 | 1999-03-25 | Mitsubishi-Tokyo Pharmaceuticals, Inc. | Composes d'imidazoline |
| US6384461B1 (en) * | 1999-10-15 | 2002-05-07 | Xerox Corporation | Dual dielectric structure for suppressing lateral leakage current in high fill factor arrays |
| US7179483B2 (en) | 2000-04-26 | 2007-02-20 | Watson Pharmaceuticals, Inc. | Compositions and methods for transdermal oxybutynin therapy |
| JP5684964B2 (ja) * | 2000-06-07 | 2015-03-18 | ワトソン ファーマシューティカルズ， インコーポレイテッド | （ｒ）−オキシブチニンおよび（ｒ）−デスエチルオキシブチニンによる平滑筋機能亢進の処置 |
| US6818659B2 (en) * | 2001-11-06 | 2004-11-16 | Bristol-Myers Squibb Pharma, Inc. | (2S)-2-amino-4-(2-amino-(3,4,5,6-tetrahydropyrimidin-4-yl) butanoyl and its use in cyclic and acyclic peptides |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB593659A (en) * | 1945-06-19 | 1947-10-22 | Boots Pure Drug Co Ltd | Improvements relating to the manufacture of heterocyclic amines |
| US3126381A (en) * | 1964-03-24 | Cghschzcooh | ||
| US3205232A (en) * | 1961-08-17 | 1965-09-07 | Socony Mobil Oil Co Inc | Salts of tetrahydropyrimidines and nu-alkyl succinamic acids |
| DE1189998B (de) * | 1961-11-14 | 1965-04-01 | Basf Ag | Verfahren zur Herstellung von cyclischen Formamidinen |
| US3483203A (en) * | 1966-03-22 | 1969-12-09 | Ciba Geigy Corp | 2-aralkyl-1,3-diaza-2-cycloalkenes |
| US3502578A (en) * | 1966-06-30 | 1970-03-24 | Shell Oil Co | Corrosion inhibiting method and composition therefor |
| DE1695601A1 (de) * | 1968-02-08 | 1972-04-13 | Pfizer | In 2-Stellung der AEthylgruppe substituierte cyclische 2-(ss-Hydroxyaethyl)-amidine und Verfahren zu ihrer Herstellung,sowie Verfahren zur Herstellung von in 2-Stellung der Vinylgruppe substituierten cyclischen 2-Vinylamidinen |
| DE2154948A1 (de) * | 1971-11-05 | 1973-05-10 | Huels Chemische Werke Ag | Verfahren zur herstellung von cyclischen amidinen |
-
1987
- 1987-09-21 IT IT8721976A patent/IT1231237B/it active
-
1988
- 1988-09-09 SU SU884356369A patent/SU1676446A3/ru active
- 1988-09-13 US US07/243,942 patent/US4973592A/en not_active Expired - Fee Related
- 1988-09-15 DD DD88319829A patent/DD282457A5/de not_active IP Right Cessation
- 1988-09-19 PL PL27475088A patent/PL274750A1/xx unknown
- 1988-09-19 EP EP88830377A patent/EP0309425A3/fr not_active Withdrawn
- 1988-09-19 PT PT88542A patent/PT88542A/pt not_active Application Discontinuation
- 1988-09-19 PL PL27934388A patent/PL279343A1/xx unknown
- 1988-09-19 PL PL27934588A patent/PL279345A1/xx unknown
- 1988-09-19 PL PL27934488A patent/PL279344A1/xx unknown
- 1988-09-19 PL PL27934288A patent/PL279342A1/xx unknown
- 1988-09-19 PT PT88545A patent/PT88545B/pt not_active IP Right Cessation
- 1988-09-20 YU YU01772/88A patent/YU177288A/xx unknown
- 1988-09-20 HU HU884928A patent/HUT56553A/hu unknown
- 1988-09-20 NO NO88884175A patent/NO884175L/no unknown
- 1988-09-20 FI FI884303A patent/FI884303A7/fi not_active IP Right Cessation
- 1988-09-20 DK DK522888A patent/DK522888A/da not_active Application Discontinuation
- 1988-09-20 JP JP63236176A patent/JPH01128970A/ja active Pending
- 1988-09-20 ZA ZA887002A patent/ZA887002B/xx unknown
- 1988-09-21 KR KR1019880012170A patent/KR890005063A/ko not_active Withdrawn
- 1988-09-21 AU AU22377/88A patent/AU2237788A/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| US4973592A (en) | 1990-11-27 |
| PL279345A1 (en) | 1990-01-08 |
| FI884303A0 (fi) | 1988-09-20 |
| NO884175D0 (no) | 1988-09-20 |
| DK522888D0 (da) | 1988-09-20 |
| PL279344A1 (en) | 1990-01-08 |
| PL279342A1 (en) | 1990-01-08 |
| PT88545A (pt) | 1988-10-01 |
| PL274750A1 (en) | 1989-09-04 |
| DK522888A (da) | 1989-03-22 |
| EP0309425A2 (fr) | 1989-03-29 |
| PL279343A1 (en) | 1990-01-08 |
| PT88545B (pt) | 1992-11-30 |
| IT1231237B (it) | 1991-11-26 |
| KR890005063A (ko) | 1989-05-11 |
| HUT56553A (en) | 1991-09-30 |
| PT88542A (pt) | 1989-07-31 |
| AU2237788A (en) | 1989-03-23 |
| IT8721976A0 (it) | 1987-09-21 |
| SU1676446A3 (ru) | 1991-09-07 |
| JPH01128970A (ja) | 1989-05-22 |
| FI884303A7 (fi) | 1989-03-22 |
| ZA887002B (en) | 1990-05-30 |
| NO884175L (no) | 1989-03-22 |
| EP0309425A3 (fr) | 1990-06-27 |
| YU177288A (en) | 1990-06-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ENJ | Ceased due to non-payment of renewal fee |