CN1078468A - 磺酰苄基取代的吡啶酮 - Google Patents

磺酰苄基取代的吡啶酮 Download PDF

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Publication number: CN1078468A
Authority: CN; China
Prior art keywords: carbon atoms; straight; group; branched alkyl; branched
Prior art date: 1992-02-27
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.): Pending

Application number

CN 93102232

Other languages

English (en)

Chinese (zh)

Inventor

R·汉科

J·德雷塞尔

P·费

W·胡布什

T·克雷默

U·E·米勒

M·米勒-格里曼

M·博克

S·卡茨达

C·赫思-迪特里希

A·克诺尔

J·-P·施塔什

S·沃尔费尔

O·亚尔金诺格鲁

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Bayer AG

Original Assignee

Bayer AG

Priority date (The priority date 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 date listed.)

1992-02-27

Filing date

1993-02-27

Publication date

1993-11-17

1993-02-27 Application filed by Bayer AG filed Critical Bayer AG

1993-11-17 Publication of CN1078468A publication Critical patent/CN1078468A/zh

Status Pending legal-status Critical Current

Links

-1 Sulphonylbenzyl Chemical group 0.000 title claims abstract description 40
LVWZTYCIRDMTEY-UHFFFAOYSA-N metamizole Chemical compound O=C1C(N(CS(O)(=O)=O)C)=C(C)N(C)N1C1=CC=CC=C1 LVWZTYCIRDMTEY-UHFFFAOYSA-N 0.000 title claims abstract description 19
150000001875 compounds Chemical class 0.000 claims abstract description 80
239000003814 drug Substances 0.000 claims abstract description 9
125000004432 carbon atom Chemical group C* 0.000 claims description 96
125000000217 alkyl group Chemical group 0.000 claims description 66
239000001257 hydrogen Substances 0.000 claims description 44
229910052739 hydrogen Inorganic materials 0.000 claims description 44
150000002431 hydrogen Chemical class 0.000 claims description 38
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 25
125000003545 alkoxy group Chemical group 0.000 claims description 24
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 22
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
239000003513 alkali Substances 0.000 claims description 17
238000000034 method Methods 0.000 claims description 16
239000000460 chlorine Substances 0.000 claims description 15
150000003839 salts Chemical class 0.000 claims description 15
125000005010 perfluoroalkyl group Chemical group 0.000 claims description 14
239000002253 acid Substances 0.000 claims description 12
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 12
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 11
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 10
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 10
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 10
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 10
229910052794 bromium Inorganic materials 0.000 claims description 10
229910052801 chlorine Inorganic materials 0.000 claims description 10
125000004093 cyano group Chemical group *C#N 0.000 claims description 10
125000004433 nitrogen atom Chemical group N* 0.000 claims description 10
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 10
229910052799 carbon Inorganic materials 0.000 claims description 9
238000002360 preparation method Methods 0.000 claims description 9
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 8
239000011737 fluorine Substances 0.000 claims description 8
229910052731 fluorine Inorganic materials 0.000 claims description 8
125000000623 heterocyclic group Chemical group 0.000 claims description 8
125000005936 piperidyl group Chemical group 0.000 claims description 8
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 8
125000002252 acyl group Chemical group 0.000 claims description 7
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 claims description 7
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 6
150000002148 esters Chemical class 0.000 claims description 6
230000009435 amidation Effects 0.000 claims description 5
238000007112 amidation reaction Methods 0.000 claims description 5
239000003960 organic solvent Substances 0.000 claims description 5
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 4
230000029936 alkylation Effects 0.000 claims description 4
238000005804 alkylation reaction Methods 0.000 claims description 4
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 4
125000004122 cyclic group Chemical group 0.000 claims description 4
125000000753 cycloalkyl group Chemical group 0.000 claims description 4
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 4
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
125000002757 morpholinyl group Chemical group 0.000 claims description 4
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
229920006395 saturated elastomer Polymers 0.000 claims description 4
230000003143 atherosclerotic effect Effects 0.000 claims description 3
125000001544 thienyl group Chemical group 0.000 claims description 3
150000001408 amides Chemical class 0.000 claims description 2
125000003710 aryl alkyl group Chemical group 0.000 claims description 2
125000003118 aryl group Chemical group 0.000 claims description 2
230000008859 change Effects 0.000 claims description 2
238000007796 conventional method Methods 0.000 claims description 2
230000032050 esterification Effects 0.000 claims description 2
238000005886 esterification reaction Methods 0.000 claims description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
125000001153 fluoro group Chemical group F* 0.000 claims description 2
RLWXXXHAQBWSPA-UHFFFAOYSA-N fluoromethanol Chemical compound OCF RLWXXXHAQBWSPA-UHFFFAOYSA-N 0.000 claims description 2
125000005842 heteroatom Chemical group 0.000 claims description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
229910052757 nitrogen Inorganic materials 0.000 claims description 2
125000001424 substituent group Chemical group 0.000 claims description 2
229910052717 sulfur Inorganic materials 0.000 claims description 2
229910052736 halogen Inorganic materials 0.000 claims 4
150000002367 halogens Chemical class 0.000 claims 4
238000004519 manufacturing process Methods 0.000 claims 1
238000006243 chemical reaction Methods 0.000 abstract description 18
201000001320 Atherosclerosis Diseases 0.000 abstract description 2
229940079593 drug Drugs 0.000 abstract 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 78
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 48
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 48
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 44
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 30
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 27
239000002904 solvent Substances 0.000 description 26
239000000203 mixture Substances 0.000 description 21
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 18
239000000243 solution Substances 0.000 description 18
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 17
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 15
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 13
238000004587 chromatography analysis Methods 0.000 description 13
239000000047 product Substances 0.000 description 13
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
239000003921 oil Substances 0.000 description 12
102000015427 Angiotensins Human genes 0.000 description 10
108010064733 Angiotensins Proteins 0.000 description 10
238000001035 drying Methods 0.000 description 10
239000011541 reaction mixture Substances 0.000 description 10
235000019580 granularity Nutrition 0.000 description 9
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 8
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 8
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
210000004027 cell Anatomy 0.000 description 8
238000001816 cooling Methods 0.000 description 8
230000000694 effects Effects 0.000 description 8
238000005406 washing Methods 0.000 description 8
230000007062 hydrolysis Effects 0.000 description 7
238000006460 hydrolysis reaction Methods 0.000 description 7
239000000463 material Substances 0.000 description 7
229910052760 oxygen Inorganic materials 0.000 description 7
238000012360 testing method Methods 0.000 description 7
GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
241000700159 Rattus Species 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
239000000556 agonist Substances 0.000 description 6
239000007789 gas Substances 0.000 description 6
230000005764 inhibitory process Effects 0.000 description 6
239000012074 organic phase Substances 0.000 description 6
150000003053 piperidines Chemical class 0.000 description 6
239000000741 silica gel Substances 0.000 description 6
229910002027 silica gel Inorganic materials 0.000 description 6
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 6
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 6
PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 5
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 5
206010020772 Hypertension Diseases 0.000 description 5
229930182821 L-proline Natural products 0.000 description 5
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
229910052728 basic metal Inorganic materials 0.000 description 5
150000003818 basic metals Chemical class 0.000 description 5
230000008602 contraction Effects 0.000 description 5
239000000706 filtrate Substances 0.000 description 5
239000007788 liquid Substances 0.000 description 5
210000003205 muscle Anatomy 0.000 description 5
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 5
235000015320 potassium carbonate Nutrition 0.000 description 5
OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 4
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
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CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 4
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
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VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
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BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
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UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
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CZGUSIXMZVURDU-JZXHSEFVSA-N Ile(5)-angiotensin II 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](CC=1C=CC=CC=1)C([O-])=O)NC(=O)[C@@H](NC(=O)[C@H](CCCNC(N)=[NH2+])NC(=O)[C@@H]([NH3+])CC([O-])=O)C(C)C)C1=CC=C(O)C=C1 CZGUSIXMZVURDU-JZXHSEFVSA-N 0.000 description 3
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QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
229930182817 methionine Natural products 0.000 description 1
JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
235000010446 mineral oil Nutrition 0.000 description 1
239000012046 mixed solvent Substances 0.000 description 1
238000002156 mixing Methods 0.000 description 1
230000002969 morbid Effects 0.000 description 1
230000002107 myocardial effect Effects 0.000 description 1
210000000107 myocyte Anatomy 0.000 description 1
PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
YZMHQCWXYHARLS-UHFFFAOYSA-N naphthalene-1,2-disulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(S(=O)(=O)O)=CC=C21 YZMHQCWXYHARLS-UHFFFAOYSA-N 0.000 description 1
229940105631 nembutal Drugs 0.000 description 1
LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
210000000056 organ Anatomy 0.000 description 1
230000008520 organization Effects 0.000 description 1
125000002971 oxazolyl group Chemical group 0.000 description 1
230000007170 pathology Effects 0.000 description 1
HSMKTIKKPMTUQH-WBPXWQEISA-L pentolinium tartrate Chemical compound OC(=O)[C@H](O)[C@@H](O)C([O-])=O.OC(=O)[C@H](O)[C@@H](O)C([O-])=O.C1CCC[N+]1(C)CCCCC[N+]1(C)CCCC1 HSMKTIKKPMTUQH-WBPXWQEISA-L 0.000 description 1
229950008637 pentolonium Drugs 0.000 description 1
230000003836 peripheral circulation Effects 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
OAHKWDDSKCRNFE-UHFFFAOYSA-N phenylmethanesulfonyl chloride Chemical compound ClS(=O)(=O)CC1=CC=CC=C1 OAHKWDDSKCRNFE-UHFFFAOYSA-N 0.000 description 1
FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
239000006187 pill Substances 0.000 description 1
230000002980 postoperative effect Effects 0.000 description 1
NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical class [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 1
235000007715 potassium iodide Nutrition 0.000 description 1
229960004839 potassium iodide Drugs 0.000 description 1
239000004540 pour-on Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
230000002797 proteolythic effect Effects 0.000 description 1
238000000746 purification Methods 0.000 description 1
239000012264 purified product Substances 0.000 description 1
125000003373 pyrazinyl group Chemical group 0.000 description 1
125000003226 pyrazolyl group Chemical group 0.000 description 1
125000002098 pyridazinyl group Chemical group 0.000 description 1
ZZYXNRREDYWPLN-UHFFFAOYSA-N pyridine-2,3-diamine Chemical compound NC1=CC=CN=C1N ZZYXNRREDYWPLN-UHFFFAOYSA-N 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
125000000714 pyrimidinyl group Chemical group 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
238000001525 receptor binding assay Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
210000002254 renal artery Anatomy 0.000 description 1
230000036454 renin-angiotensin system Effects 0.000 description 1
230000004044 response Effects 0.000 description 1
230000028327 secretion Effects 0.000 description 1
238000000926 separation method Methods 0.000 description 1
229940076279 serotonin Drugs 0.000 description 1
210000002966 serum Anatomy 0.000 description 1
229910052709 silver Inorganic materials 0.000 description 1
239000004332 silver Substances 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
238000002798 spectrophotometry method Methods 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
230000004936 stimulating effect Effects 0.000 description 1
210000002784 stomach Anatomy 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
238000000967 suction filtration Methods 0.000 description 1
125000000542 sulfonic acid group Chemical group 0.000 description 1
238000001356 surgical procedure Methods 0.000 description 1
210000002820 sympathetic nervous system Anatomy 0.000 description 1
230000001360 synchronised effect Effects 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
125000000335 thiazolyl group Chemical group 0.000 description 1
AWLILQARPMWUHA-UHFFFAOYSA-M thiopental sodium Chemical compound [Na+].CCCC(C)C1(CC)C(=O)NC([S-])=NC1=O AWLILQARPMWUHA-UHFFFAOYSA-M 0.000 description 1
229960000340 thiopental sodium Drugs 0.000 description 1
229940104230 thymidine Drugs 0.000 description 1
210000001519 tissue Anatomy 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
125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
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
230000002792 vascular Effects 0.000 description 1
230000003639 vasoconstrictive effect Effects 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- 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
- 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
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- 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
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6558—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system
- C07F9/65583—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system each of the hetero rings containing nitrogen as ring hetero atom

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Veterinary Medicine (AREA)
Molecular Biology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Cardiology (AREA)
Animal Behavior & Ethology (AREA)
Heart & Thoracic Surgery (AREA)
Public Health (AREA)
Biochemistry (AREA)
Urology & Nephrology (AREA)
Vascular Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Pyridine Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Cephalosporin Compounds (AREA)

CN 93102232 1992-02-27 1993-02-27 磺酰苄基取代的吡啶酮 Pending CN1078468A (zh)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DEP4206045.1		1992-02-27
DE4206045A DE4206045A1 (de)	1992-02-27	1992-02-27	Sulfonylbenzyl substituierte pyridone

Publications (1)

Publication Number	Publication Date
CN1078468A true CN1078468A (zh)	1993-11-17

Family

ID=6452730

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CN 93102232 Pending CN1078468A (zh)	1992-02-27	1993-02-27	磺酰苄基取代的吡啶酮

Country Status (18)

Country	Link
US (1)	US5254543A (2)
EP (1)	EP0557843A3 (2)
JP (1)	JPH0641081A (2)
KR (1)	KR930017898A (2)
CN (1)	CN1078468A (2)
AU (1)	AU653288B2 (2)
CA (1)	CA2090267A1 (2)
CZ (1)	CZ15793A3 (2)
DE (1)	DE4206045A1 (2)
HU (1)	HUT64057A (2)
IL (1)	IL104843A0 (2)
MX (1)	MX9300766A (2)
MY (1)	MY129973A (2)
NZ (1)	NZ245999A (2)
PL (1)	PL297870A1 (2)
SK (1)	SK14593A3 (2)
TW (1)	TW230206B (2)
ZA (1)	ZA931370B (2)

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CN1985878B (zh) *	2005-12-20	2011-06-22	广州王老吉药业股份有限公司	一种治疗消化性溃疡的药物组合物及其制备方法

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TW200303742A (en) *	2001-11-21	2003-09-16	Novartis Ag	Organic compounds
US7482366B2 (en)	2001-12-21	2009-01-27	X-Ceptor Therapeutics, Inc.	Modulators of LXR
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GB0316546D0 (en) *	2003-07-15	2003-08-20	Novartis Ag	Process for the manufacture of organic compounds
CN101277949A (zh)	2005-04-22	2008-10-01	阿兰托斯制药控股公司	二肽基肽酶-ⅳ抑制剂
GB0514686D0 (en) *	2005-07-18	2005-08-24	Novartis Ag	Organic compounds
TWI417095B (zh) *	2006-03-15	2013-12-01	Janssen Pharmaceuticals Inc	１，４-二取代之３-氰基-吡啶酮衍生物及其作為ｍＧｌｕＲ２-受體之正向異位性調節劑之用途
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KR20100065191A (ko)	2007-09-14	2010-06-15	오르토-맥닐-얀센 파마슈티칼스 인코포레이티드	１,３-이치환된 ４-(아릴-ｘ-페닐)-１ｈ-피리딘-２-온
CA2696948C (en) *	2007-09-14	2013-04-30	Jose Maria Cid-Nunez	1',3'-disubstituted-4-phenyl-3,4,5,6-tetrahydro-2h,1'h-[1,4']bipyridinyl-2'-ones
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AU2009304293B2 (en)	2008-10-16	2012-04-26	Addex Pharma S.A.	Indole and benzomorpholine derivatives as modulators of metabotropic glutamate receptors
BRPI0921333A2 (pt)	2008-11-28	2015-12-29	Addex Pharmaceuticals Sa	derivados de indol e benzoxazina como moduladores de receptores de glutamato metabotrópicos
BRPI0923488A2 (pt)	2008-12-23	2019-09-24	Hoffmann La Roche	amidas de didropiridona como modulares p2x7
JP5478637B2 (ja)	2008-12-23	2014-04-23	エフ．ホフマン−ラロシュアーゲー	Ｐ２ｘ７モジュレーターとしてのジヒドロピリドンアミド
EP2393781B1 (en)	2008-12-23	2014-03-12	F. Hoffmann-La Roche AG	Dihydropyridone ureas as p2x7 modulators
CA2745952A1 (en)	2008-12-23	2010-07-01	F.Hoffmann-La Roche Ag	Dihydropyridone amides as p2x7 modulators
US8153808B2 (en)	2008-12-23	2012-04-10	Roche Palo Alto Llc	Dihydropyridone amides as P2X7 modulators
MY153913A (en)	2009-05-12	2015-04-15	Janssen Pharmaceuticals Inc	7-aryl-1,2,4-triazolo[4,3-a]pyridine derivatives and their use as positive allosteric modulators of mglur2 receptors
NZ596078A (en)	2009-05-12	2013-06-28	Janssen Pharmaceuticals Inc	1,2,4-TRIAZOLO [4,3-a] PYRIDINE DERIVATIVES AND THEIR USE FOR THE TREATMENT OR PREVENTION OF NEUROLOGICAL AND PSYCHIATRIC DISORDERS
EA020671B1 (ru)	2009-05-12	2014-12-30	Янссен Фармасьютикалз, Инк.	ПРОИЗВОДНЫЕ 1,2,4-ТРИАЗОЛО[4,3-a]ПИРИДИНА И ИХ ПРИМЕНЕНИЕ В КАЧЕСТВЕ ПОЛОЖИТЕЛЬНЫХ АЛЛОСТЕРИЧЕСКИХ МОДУЛЯТОРОВ РЕЦЕПТОРОВ mGluR2
CA2815002C (en)	2010-11-08	2019-10-22	Janssen Pharmaceuticals, Inc.	1,2,4-triazolo[4,3-a]pyridine derivatives and their use as positive allosteric modulators of mglur2 receptors
CN103298810B (zh)	2010-11-08	2016-03-16	杨森制药公司	1,2,4-三唑并[4,3-a]吡啶衍生物及其作为MGLUR2受体的正变构调节剂的用途
EP2643320B1 (en)	2010-11-08	2015-03-04	Janssen Pharmaceuticals, Inc.	1,2,4-TRIAZOLO[4,3-a]PYRIDINE DERIVATIVES AND THEIR USE AS POSITIVE ALLOSTERIC MODULATORS OF MGLUR2 RECEPTORS
JO3368B1 (ar)	2013-06-04	2019-03-13	Janssen Pharmaceutica Nv	مركبات 6، 7- ثاني هيدرو بيرازولو [5،1-a] بيرازين- 4 (5 يد)- اون واستخدامها بصفة منظمات تفارغية سلبية لمستقبلات ميجلور 2
JO3367B1 (ar)	2013-09-06	2019-03-13	Janssen Pharmaceutica Nv	مركبات 2،1، 4- ثلاثي زولو [3،4-a] بيريدين واستخدامها بصفة منظمات تفارغية موجبة لمستقبلات ميجلور 2
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1992
- 1992-02-27 DE DE4206045A patent/DE4206045A1/de not_active Withdrawn
1993
- 1993-02-06 TW TW082100802A patent/TW230206B/zh active
- 1993-02-09 CZ CZ93157A patent/CZ15793A3/cs unknown
- 1993-02-12 MX MX9300766A patent/MX9300766A/es unknown
- 1993-02-15 EP EP19930102326 patent/EP0557843A3/de not_active Withdrawn
- 1993-02-18 US US08/019,000 patent/US5254543A/en not_active Expired - Fee Related
- 1993-02-24 AU AU33770/93A patent/AU653288B2/en not_active Ceased
- 1993-02-24 CA CA002090267A patent/CA2090267A1/en not_active Abandoned
- 1993-02-24 IL IL104843A patent/IL104843A0/xx unknown
- 1993-02-25 PL PL29787093A patent/PL297870A1/xx unknown
- 1993-02-25 JP JP5061017A patent/JPH0641081A/ja active Pending
- 1993-02-25 NZ NZ245999A patent/NZ245999A/en unknown
- 1993-02-26 KR KR1019930002728A patent/KR930017898A/ko not_active Withdrawn
- 1993-02-26 ZA ZA931370A patent/ZA931370B/xx unknown
- 1993-02-26 MY MYPI93000350A patent/MY129973A/en unknown
- 1993-02-26 HU HU9300545A patent/HUT64057A/hu unknown
- 1993-02-26 SK SK14593A patent/SK14593A3/sk unknown
- 1993-02-27 CN CN 93102232 patent/CN1078468A/zh active Pending

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN1985878B (zh) *	2005-12-20	2011-06-22	广州王老吉药业股份有限公司	一种治疗消化性溃疡的药物组合物及其制备方法

Also Published As

Publication number	Publication date
AU653288B2 (en)	1994-09-22
PL297870A1 (en)	1993-10-04
AU3377093A (en)	1993-09-02
ZA931370B (en)	1993-03-23
MX9300766A (es)	1993-08-01
MY129973A (en)	2007-05-31
CA2090267A1 (en)	1993-08-28
IL104843A0 (en)	1993-06-10
EP0557843A3 (en)	1993-12-01
SK14593A3 (en)	1993-10-06
US5254543A (en)	1993-10-19
EP0557843A2 (de)	1993-09-01
DE4206045A1 (de)	1993-09-02
HU9300545D0 (en)	1993-05-28
KR930017898A (ko)	1993-09-20
HUT64057A (en)	1993-11-29
CZ15793A3 (en)	1993-12-15
TW230206B (2)	1994-09-11
NZ245999A (en)	1995-10-26
JPH0641081A (ja)	1994-02-15

Legal Events

Date	Code	Title
1993-11-17	C06	Publication
1993-11-17	PB01	Publication
1994-12-28	C10	Entry into substantive examination
1994-12-28	SE01	Entry into force of request for substantive examination
1998-04-22	C01	Deemed withdrawal of patent application (patent law 1993)
1998-04-22	WD01	Invention patent application deemed withdrawn after publication

Publication	Publication Date	Title
CN1038935C (zh)	1998-07-01	取代的联苯吡啶酮化合物及其盐的制备方法
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CN1078468A - 磺酰苄基取代的吡啶酮 - Google Patents

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