JPH0134991B2 - - Google Patents
Info
- Publication number
- JPH0134991B2 JPH0134991B2 JP5167481A JP5167481A JPH0134991B2 JP H0134991 B2 JPH0134991 B2 JP H0134991B2 JP 5167481 A JP5167481 A JP 5167481A JP 5167481 A JP5167481 A JP 5167481A JP H0134991 B2 JPH0134991 B2 JP H0134991B2
- Authority
- JP
- Japan
- Prior art keywords
- ono
- benzopyran
- dihydro
- value
- group
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- -1 haloacyloxy group Chemical group 0.000 claims description 9
- KYNSBQPICQTCGU-UHFFFAOYSA-N Benzopyrane Chemical group C1=CC=C2C=CCOC2=C1 KYNSBQPICQTCGU-UHFFFAOYSA-N 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 125000002252 acyl group Chemical group 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000004423 acyloxy group Chemical group 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 125000005194 alkoxycarbonyloxy group Chemical group 0.000 claims description 2
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims description 2
- 125000005336 allyloxy group Chemical group 0.000 claims description 2
- 125000005279 aryl sulfonyloxy group Chemical group 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- CHNUOJQWGUIOLD-NFZZJPOKSA-N epalrestat Chemical compound C=1C=CC=CC=1\C=C(/C)\C=C1/SC(=S)N(CC(O)=O)C1=O CHNUOJQWGUIOLD-NFZZJPOKSA-N 0.000 description 125
- 125000003118 aryl group Chemical group 0.000 description 82
- 239000007788 liquid Substances 0.000 description 47
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 33
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 27
- 239000013078 crystal Substances 0.000 description 25
- 239000002904 solvent Substances 0.000 description 22
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- 238000002844 melting Methods 0.000 description 19
- 230000008018 melting Effects 0.000 description 19
- 239000000243 solution Substances 0.000 description 19
- 150000001875 compounds Chemical class 0.000 description 17
- 239000004593 Epoxy Substances 0.000 description 16
- 229910052760 oxygen Inorganic materials 0.000 description 16
- 238000003756 stirring Methods 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 15
- 229910052739 hydrogen Inorganic materials 0.000 description 15
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 13
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 238000010898 silica gel chromatography Methods 0.000 description 10
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 6
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 6
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 6
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 6
- 238000001816 cooling Methods 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 239000002198 insoluble material Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 3
- 239000012528 membrane Substances 0.000 description 3
- 239000012452 mother liquor Substances 0.000 description 3
- 229910001961 silver nitrate Inorganic materials 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 2
- NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 description 2
- 229910002651 NO3 Inorganic materials 0.000 description 2
- 150000001562 benzopyrans Chemical group 0.000 description 2
- QTMDXZNDVAMKGV-UHFFFAOYSA-L copper(ii) bromide Chemical compound [Cu+2].[Br-].[Br-] QTMDXZNDVAMKGV-UHFFFAOYSA-L 0.000 description 2
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 2
- 229910017604 nitric acid Inorganic materials 0.000 description 2
- WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 235000009518 sodium iodide Nutrition 0.000 description 2
- 230000035488 systolic blood pressure Effects 0.000 description 2
- GSIDPBZVWJGZDA-UHFFFAOYSA-N (8-hydroxy-6-methoxy-3,4-dihydro-2h-chromen-3-yl)methyl methanesulfonate Chemical compound O1CC(COS(C)(=O)=O)CC2=CC(OC)=CC(O)=C21 GSIDPBZVWJGZDA-UHFFFAOYSA-N 0.000 description 1
- HMXJOWDZAJWLTF-UHFFFAOYSA-N 2h-chromene-2-carboxylic acid Chemical compound C1=CC=C2C=CC(C(=O)O)OC2=C1 HMXJOWDZAJWLTF-UHFFFAOYSA-N 0.000 description 1
- AEGZSOBDIZYPGN-UHFFFAOYSA-N 3-(hydroxymethyl)-3,4-dihydro-2h-chromen-8-ol Chemical compound C1=CC=C2CC(CO)COC2=C1O AEGZSOBDIZYPGN-UHFFFAOYSA-N 0.000 description 1
- YAESPGUTBOSZQY-UHFFFAOYSA-N 3-(hydroxymethyl)-6-methoxy-3,4-dihydro-2h-chromen-8-ol Chemical compound O1CC(CO)CC2=CC(OC)=CC(O)=C21 YAESPGUTBOSZQY-UHFFFAOYSA-N 0.000 description 1
- 229910021590 Copper(II) bromide Inorganic materials 0.000 description 1
- 239000004129 EU approved improving agent Substances 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- 229910004679 ONO2 Inorganic materials 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 1
- 125000005157 alkyl carboxy group Chemical group 0.000 description 1
- KZTZJUQNSSLNAG-UHFFFAOYSA-N aminoethyl nitrate Chemical compound NCCO[N+]([O-])=O KZTZJUQNSSLNAG-UHFFFAOYSA-N 0.000 description 1
- 239000004004 anti-anginal agent Substances 0.000 description 1
- 230000003276 anti-hypertensive effect Effects 0.000 description 1
- 229940124345 antianginal agent Drugs 0.000 description 1
- 239000002220 antihypertensive agent Substances 0.000 description 1
- 229940030600 antihypertensive agent Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- AVLIGBBBDNWHFL-UHFFFAOYSA-N ethyl (3-hydroxy-3,4-dihydro-2h-chromen-8-yl) carbonate Chemical compound C1C(O)COC2=C1C=CC=C2OC(=O)OCC AVLIGBBBDNWHFL-UHFFFAOYSA-N 0.000 description 1
- LNOFDINSFMGNGX-UHFFFAOYSA-N ethyl [3-(hydroxymethyl)-3,4-dihydro-2h-chromen-8-yl] carbonate Chemical compound C1C(CO)COC2=C1C=CC=C2OC(=O)OCC LNOFDINSFMGNGX-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 230000001077 hypotensive effect Effects 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- JCZMXVGQBBATMY-UHFFFAOYSA-N nitro acetate Chemical compound CC(=O)O[N+]([O-])=O JCZMXVGQBBATMY-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229960001412 pentobarbital Drugs 0.000 description 1
- 230000003836 peripheral circulation Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000029058 respiratory gaseous exchange Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000000304 vasodilatating effect Effects 0.000 description 1
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5167481A JPS57167981A (en) | 1981-04-08 | 1981-04-08 | Benzopyran derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5167481A JPS57167981A (en) | 1981-04-08 | 1981-04-08 | Benzopyran derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS57167981A JPS57167981A (en) | 1982-10-16 |
| JPH0134991B2 true JPH0134991B2 (de) | 1989-07-21 |
Family
ID=12893421
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP5167481A Granted JPS57167981A (en) | 1981-04-08 | 1981-04-08 | Benzopyran derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS57167981A (de) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA93436B (en) * | 1992-01-24 | 1993-08-25 | Chugai Pharmaceutical Co Ltd | Benzopyran derivatives |
| JP2710277B2 (ja) * | 1995-12-27 | 1998-02-10 | 株式会社リコー | 画像形成装置における両面ユニット |
| WO2013060673A1 (en) * | 2011-10-24 | 2013-05-02 | Nicox S.A. | Quinone based nitric oxide donating compounds |
-
1981
- 1981-04-08 JP JP5167481A patent/JPS57167981A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS57167981A (en) | 1982-10-16 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| FI70406B (fi) | Foerfarande foer framstaellning av farmaceutiskt aktiva karbazolyl-(4)-oxi-propanolamin-derivat | |
| EP0200739B1 (de) | Verfahren zur herstellung von (threo)-1-aryl-2-acylamido-3-fluoro-1-propanole | |
| JPH05394B2 (de) | ||
| US4845094A (en) | 2-phenylbenzoxepin derivative | |
| NL8303066A (nl) | Carbostyrilderivaten, alsmede zouten daarvan, werkwijzen ter bereiding daarvan en farmaceutische preparaten, die deze derivaten bevatten. | |
| KR850000193B1 (ko) | 벤조피란 화합물의 제조방법 | |
| JPS6130652B2 (de) | ||
| CZ187294A3 (en) | Novel derivatives of baccatin iii and 10-deacetylbaccatin iii, process of their preparation and pharmaceutical compositions containing thereof | |
| EP0314446A2 (de) | Antihypertensive Benzopyran-Derivate | |
| JPH0134991B2 (de) | ||
| JPH0471072B2 (de) | ||
| JPH0610174B2 (ja) | アミノフエノ−ル誘導体 | |
| EP0157623B1 (de) | Optisch wirksame Isomere von Benzopyran-Derivaten verwendbar für die Behandlung von kardiovaskularen Krankheiten | |
| JP2980749B2 (ja) | フラン誘導体 | |
| JPH0213671B2 (de) | ||
| JPS6054317B2 (ja) | 新規ベンゾピラン誘導体 | |
| JP3348860B2 (ja) | グリシジルエーテルの製造法 | |
| JPH0696572B2 (ja) | ピリドンカルボン酸誘導体、そのエステルおよびその塩 | |
| KR950009862B1 (ko) | 벤조피란 유도체와 그의 제조방법(1) | |
| JPH0227987B2 (de) | ||
| DK142575B (da) | 4-hydroxyindazolderivater til anvendelse som mellemprodukter til fremstilling af indazolyl-(4)-oxy-propanolaminderivater med betareceptorblokerende virkning | |
| JPH0150218B2 (de) | ||
| JPH07215965A (ja) | インドールスルホンアミド−置換ジヒドロピリジン類 | |
| JPH07247284A (ja) | クロマン誘導体及びその用途 | |
| JPH0570452A (ja) | 光学活性化合物の製造法 |