JPH0149259B2 - - Google Patents
Info
- Publication number
- JPH0149259B2 JPH0149259B2 JP15318783A JP15318783A JPH0149259B2 JP H0149259 B2 JPH0149259 B2 JP H0149259B2 JP 15318783 A JP15318783 A JP 15318783A JP 15318783 A JP15318783 A JP 15318783A JP H0149259 B2 JPH0149259 B2 JP H0149259B2
- Authority
- JP
- Japan
- Prior art keywords
- azulene
- compound
- alkyl group
- lower alkyl
- sodium
- 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
- 150000001875 compounds Chemical class 0.000 claims description 36
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- HPJYKMSFRBJOSW-JHSUYXJUSA-N Damsin Chemical compound C[C@H]1CC[C@H]2C(=C)C(=O)O[C@H]2[C@]2(C)C(=O)CC[C@@H]12 HPJYKMSFRBJOSW-JHSUYXJUSA-N 0.000 claims description 6
- 239000003699 antiulcer agent Substances 0.000 claims description 4
- 159000000000 sodium salts Chemical class 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 29
- 239000011734 sodium Substances 0.000 description 19
- 229910052708 sodium Inorganic materials 0.000 description 17
- 238000002844 melting Methods 0.000 description 14
- 230000008018 melting Effects 0.000 description 14
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 8
- -1 Sodium 1-ethyl azulene-3-sulfonate Chemical compound 0.000 description 8
- 230000000694 effects Effects 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 208000025865 Ulcer Diseases 0.000 description 6
- 230000000767 anti-ulcer Effects 0.000 description 6
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 6
- 231100000397 ulcer Toxicity 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 102000057297 Pepsin A Human genes 0.000 description 5
- 108090000284 Pepsin A Proteins 0.000 description 5
- 230000002467 anti-pepsin effect Effects 0.000 description 5
- 229940111202 pepsin Drugs 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 230000005764 inhibitory process Effects 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- WSQIUQGZWDQMEL-UHFFFAOYSA-N 1-methylazulene Chemical compound C1=CC=CC=C2C(C)=CC=C21 WSQIUQGZWDQMEL-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- ATURQTBVCVCOJX-UHFFFAOYSA-M sodium;3-butylazulene-1-sulfonate Chemical compound [Na+].C1=CC=CC=C2C(CCCC)=CC(S([O-])(=O)=O)=C21 ATURQTBVCVCOJX-UHFFFAOYSA-M 0.000 description 3
- ZSHDTSXPNKXXAV-UHFFFAOYSA-N 2-(3-methylazulen-1-yl)acetic acid Chemical compound C1=CC=CC=C2C(C)=CC(CC(O)=O)=C21 ZSHDTSXPNKXXAV-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000002835 absorbance Methods 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 229940121363 anti-inflammatory agent Drugs 0.000 description 2
- 239000002260 anti-inflammatory agent Substances 0.000 description 2
- KKEMWYNNTBRYMR-UHFFFAOYSA-N azulene-1-sulfonic acid Chemical compound C1=CC=CC=C2C(S(=O)(=O)O)=CC=C21 KKEMWYNNTBRYMR-UHFFFAOYSA-N 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 229940126214 compound 3 Drugs 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 210000001198 duodenum Anatomy 0.000 description 2
- 150000002081 enamines Chemical class 0.000 description 2
- 230000002496 gastric effect Effects 0.000 description 2
- XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 description 2
- 238000006277 sulfonation reaction Methods 0.000 description 2
- 239000013076 target substance Substances 0.000 description 2
- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 1
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 1
- UNILWMWFPHPYOR-KXEYIPSPSA-M 1-[6-[2-[3-[3-[3-[2-[2-[3-[[2-[2-[[(2r)-1-[[2-[[(2r)-1-[3-[2-[2-[3-[[2-(2-amino-2-oxoethoxy)acetyl]amino]propoxy]ethoxy]ethoxy]propylamino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-[(2r)-2,3-di(hexadecanoyloxy)propyl]sulfanyl-1-oxopropan-2-yl Chemical compound O=C1C(SCCC(=O)NCCCOCCOCCOCCCNC(=O)COCC(=O)N[C@@H](CSC[C@@H](COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(=O)NCC(=O)N[C@H](CO)C(=O)NCCCOCCOCCOCCCNC(=O)COCC(N)=O)CC(=O)N1CCNC(=O)CCCCCN\1C2=CC=C(S([O-])(=O)=O)C=C2CC/1=C/C=C/C=C/C1=[N+](CC)C2=CC=C(S([O-])(=O)=O)C=C2C1 UNILWMWFPHPYOR-KXEYIPSPSA-M 0.000 description 1
- CMAGYTOIFYNWGH-UHFFFAOYSA-N 1-ethyl-5-propan-2-ylazulene Chemical compound C1=C(C(C)C)C=CC=C2C(CC)=CC=C21 CMAGYTOIFYNWGH-UHFFFAOYSA-N 0.000 description 1
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 1
- LSQXOLFOAOCMSS-UHFFFAOYSA-N 1-pent-2-en-3-ylpyrrolidine Chemical compound CCC(=CC)N1CCCC1 LSQXOLFOAOCMSS-UHFFFAOYSA-N 0.000 description 1
- SXAMGRAIZSSWIH-UHFFFAOYSA-N 2-[3-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-1,2,4-oxadiazol-5-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1=NOC(=N1)CC(=O)N1CC2=C(CC1)NN=N2 SXAMGRAIZSSWIH-UHFFFAOYSA-N 0.000 description 1
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 1
- 206010022998 Irritability Diseases 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 108010071390 Serum Albumin Proteins 0.000 description 1
- 102000007562 Serum Albumin Human genes 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 229940098773 bovine serum albumin Drugs 0.000 description 1
- RHDGNLCLDBVESU-UHFFFAOYSA-N but-3-en-4-olide Chemical compound O=C1CC=CO1 RHDGNLCLDBVESU-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 229940125773 compound 10 Drugs 0.000 description 1
- 229940125797 compound 12 Drugs 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 229940125898 compound 5 Drugs 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- FWKQNCXZGNBPFD-UHFFFAOYSA-N guaiazulene Natural products CC(C)C1=CC=C(C)C2=CC=C(C)C2=C1 FWKQNCXZGNBPFD-UHFFFAOYSA-N 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229940087305 limonene Drugs 0.000 description 1
- 235000001510 limonene Nutrition 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 230000002797 proteolythic effect Effects 0.000 description 1
- 210000001187 pylorus Anatomy 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 229950002760 sodium gualenate Drugs 0.000 description 1
- GEYJUFBPCGDENK-UHFFFAOYSA-M sodium;3,8-dimethyl-5-propan-2-ylazulene-1-sulfonate Chemical compound [Na+].CC(C)C1=CC=C(C)C2=C(S([O-])(=O)=O)C=C(C)C2=C1 GEYJUFBPCGDENK-UHFFFAOYSA-M 0.000 description 1
- IFNWBZPEJSGLNB-UHFFFAOYSA-M sodium;3-ethylazulene-1-sulfonate Chemical compound [Na+].C1=CC=CC=C2C(CC)=CC(S([O-])(=O)=O)=C21 IFNWBZPEJSGLNB-UHFFFAOYSA-M 0.000 description 1
- IMSYLDRQZHJGJB-UHFFFAOYSA-M sodium;3-methylazulene-1-sulfonate Chemical compound [Na+].C1=CC=CC=C2C(C)=CC(S([O-])(=O)=O)=C21 IMSYLDRQZHJGJB-UHFFFAOYSA-M 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Inorganic materials O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002723 toxicity assay Methods 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
Landscapes
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (16)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15318783A JPS6048960A (ja) | 1983-08-24 | 1983-08-24 | アズレン誘導体及びその製法並びにこの化合物を有効成分とする抗潰瘍剤 |
| ZA845948A ZA845948B (en) | 1983-08-24 | 1984-08-01 | Azulene derivatives,processes of their synthesis and their uses as anti-ulcerative and anti-inflammatory agents |
| AU31396/84A AU571554B2 (en) | 1983-08-24 | 1984-08-01 | Azulene sulfonates |
| DK377984A DK169870B1 (da) | 1983-08-24 | 1984-08-03 | Azulenderivater, fremgangsmåde til deres syntese og anti-ulcerative og anti-inflammatoriske midler omfattende disse derivater |
| CA000461108A CA1228862A (en) | 1983-08-24 | 1984-08-15 | Azulene derivatives, processes of their synthesis and their uses as anti-ulcerative and anti-inflammatory agents |
| US06/642,043 US4595694A (en) | 1983-08-24 | 1984-08-17 | Azulene derivatives, processes of their synthesis and their uses as anti-ulcerative and anti-inflammatory agents |
| AT84305775T ATE26976T1 (de) | 1983-08-24 | 1984-08-23 | Azulenderivate verwendbar als antiulcusmittel und als entzuendungshemmer. |
| ES535381A ES535381A0 (es) | 1983-08-24 | 1984-08-23 | Un metodo para preparar un derivado de azuleno |
| KR1019840005107A KR920000956B1 (ko) | 1983-08-24 | 1984-08-23 | 아줄렌 유도체의 제조방법 |
| PT79119A PT79119B (en) | 1983-08-24 | 1984-08-23 | Azuren derivatives processes of their synthesis and their uses as anti-ulcerative and anti-inflammatory agents |
| NO843377A NO158673C (no) | 1983-08-24 | 1984-08-23 | Analogifremgangsmaate ved fremstilling av terapeutisk aktive azurenderivater. |
| HU843172A HU195478B (en) | 1983-08-24 | 1984-08-23 | Process for the production of azulene-derivatives |
| EP84305775A EP0147915B1 (en) | 1983-08-24 | 1984-08-23 | New azulene derivatives useful as anti-ulcerative and anti-flammatory agents |
| DE8484305775T DE3463502D1 (en) | 1983-08-24 | 1984-08-23 | New azulene derivatives useful as anti-ulcerative and anti-flammatory agents |
| SU3785251A SU1311618A3 (ru) | 1983-08-24 | 1984-08-23 | Способ получени производных азулена |
| AR29767884A AR240554A1 (es) | 1983-08-24 | 1984-08-23 | Procedimiento para preparar derivados del acido azulen-3-sulfonico y sus sales |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15318783A JPS6048960A (ja) | 1983-08-24 | 1983-08-24 | アズレン誘導体及びその製法並びにこの化合物を有効成分とする抗潰瘍剤 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6048960A JPS6048960A (ja) | 1985-03-16 |
| JPH0149259B2 true JPH0149259B2 (ko) | 1989-10-24 |
Family
ID=15556944
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP15318783A Granted JPS6048960A (ja) | 1983-08-24 | 1983-08-24 | アズレン誘導体及びその製法並びにこの化合物を有効成分とする抗潰瘍剤 |
Country Status (2)
| Country | Link |
|---|---|
| JP (1) | JPS6048960A (ko) |
| ZA (1) | ZA845948B (ko) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4880477B2 (ja) * | 2004-10-20 | 2012-02-22 | 壽製薬株式会社 | 胃粘膜疾患の治療のための医薬組成物 |
| JP5465867B2 (ja) * | 2008-11-12 | 2014-04-09 | 壽製薬株式会社 | 安定なエグアレンナトリウム固形製剤 |
| JP5878510B2 (ja) * | 2013-11-07 | 2016-03-08 | 壽製薬株式会社 | 安定なエグアレンナトリウム固形製剤 |
-
1983
- 1983-08-24 JP JP15318783A patent/JPS6048960A/ja active Granted
-
1984
- 1984-08-01 ZA ZA845948A patent/ZA845948B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6048960A (ja) | 1985-03-16 |
| ZA845948B (en) | 1985-05-29 |
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Legal Events
| Date | Code | Title | Description |
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| R250 | Receipt of annual fees |
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| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
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| EXPY | Cancellation because of completion of term |