JPS6320817B2 - - Google Patents
Info
- Publication number
- JPS6320817B2 JPS6320817B2 JP9233678A JP9233678A JPS6320817B2 JP S6320817 B2 JPS6320817 B2 JP S6320817B2 JP 9233678 A JP9233678 A JP 9233678A JP 9233678 A JP9233678 A JP 9233678A JP S6320817 B2 JPS6320817 B2 JP S6320817B2
- Authority
- JP
- Japan
- Prior art keywords
- benzazonine
- optically active
- producing
- solvent
- methano
- 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
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 25
- 239000002904 solvent Substances 0.000 claims description 10
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 9
- IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 claims description 6
- 150000007524 organic acids Chemical class 0.000 claims description 6
- QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 claims description 5
- 229960002510 mandelic acid Drugs 0.000 claims description 4
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 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 group [H]* 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims description 2
- 235000002906 tartaric acid Nutrition 0.000 claims description 2
- 239000011975 tartaric acid Substances 0.000 claims description 2
- 238000002844 melting Methods 0.000 description 9
- 230000008018 melting Effects 0.000 description 9
- 239000013078 crystal Substances 0.000 description 8
- 239000000243 solution Substances 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- ASLUVGUEPYXPRF-UHFFFAOYSA-N 1h-1-benzazonine Chemical class N1C=CC=CC=CC2=CC=CC=C21 ASLUVGUEPYXPRF-UHFFFAOYSA-N 0.000 description 5
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 5
- 235000011114 ammonium hydroxide Nutrition 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 230000003287 optical effect Effects 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- PYMCWPNDUHYOLW-UHFFFAOYSA-N 11-azatricyclo[7.4.1.02,7]tetradeca-2,4,6-triene Chemical compound C1NCCC2C3=CC=CC=C3CC1C2 PYMCWPNDUHYOLW-UHFFFAOYSA-N 0.000 description 3
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 230000000202 analgesic effect Effects 0.000 description 2
- IWYDHOAUDWTVEP-UHFFFAOYSA-M mandelate Chemical compound [O-]C(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-M 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- IWYDHOAUDWTVEP-SSDOTTSWSA-N (R)-mandelic acid Chemical compound OC(=O)[C@H](O)C1=CC=CC=C1 IWYDHOAUDWTVEP-SSDOTTSWSA-N 0.000 description 1
- IWYDHOAUDWTVEP-ZETCQYMHSA-M (S)-mandelate Chemical compound [O-]C(=O)[C@@H](O)C1=CC=CC=C1 IWYDHOAUDWTVEP-ZETCQYMHSA-M 0.000 description 1
- LUBVANRYUNXNPE-UHFFFAOYSA-N C1C=CN=CC=CC2=CC=CC=C12 Chemical compound C1C=CN=CC=CC2=CC=CC=C12 LUBVANRYUNXNPE-UHFFFAOYSA-N 0.000 description 1
- 235000011002 L(+)-tartaric acid Nutrition 0.000 description 1
- 239000001358 L(+)-tartaric acid Substances 0.000 description 1
- FEWJPZIEWOKRBE-LWMBPPNESA-N L-(+)-Tartaric acid Natural products OC(=O)[C@@H](O)[C@H](O)C(O)=O FEWJPZIEWOKRBE-LWMBPPNESA-N 0.000 description 1
- 206010027646 Miosis Diseases 0.000 description 1
- 206010039424 Salivary hypersecretion Diseases 0.000 description 1
- 206010047700 Vomiting Diseases 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 230000036592 analgesia Effects 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000009509 drug development Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- -1 hydroxy-2,3,4,5,6,7-hexahydro-1,6-methano-1H-4-benzazonine Chemical compound 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000003547 miosis Effects 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- VOKSWYLNZZRQPF-GDIGMMSISA-N pentazocine Chemical compound C1C2=CC=C(O)C=C2[C@@]2(C)[C@@H](C)[C@@H]1N(CC=C(C)C)CC2 VOKSWYLNZZRQPF-GDIGMMSISA-N 0.000 description 1
- 229960005301 pentazocine Drugs 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000036387 respiratory rate Effects 0.000 description 1
- 208000026451 salivation Diseases 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000008673 vomiting Effects 0.000 description 1
Landscapes
- Other In-Based Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9233678A JPS5536403A (en) | 1978-07-28 | 1978-07-28 | Preparation of 1-benzazonine derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9233678A JPS5536403A (en) | 1978-07-28 | 1978-07-28 | Preparation of 1-benzazonine derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5536403A JPS5536403A (en) | 1980-03-14 |
| JPS6320817B2 true JPS6320817B2 (da) | 1988-04-30 |
Family
ID=14051543
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP9233678A Granted JPS5536403A (en) | 1978-07-28 | 1978-07-28 | Preparation of 1-benzazonine derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5536403A (da) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GR75395B (da) * | 1980-11-14 | 1984-07-13 | Lilly Co Eli | |
| DE3113119A1 (de) * | 1981-03-27 | 1982-10-14 | Mannesmann AG, 4000 Düsseldorf | Dornstangen haltevorrichtung |
| JPS5874206A (ja) * | 1981-10-27 | 1983-05-04 | Sumitomo Metal Ind Ltd | 金属管の圧延設備 |
| JPH069694B2 (ja) * | 1984-10-12 | 1994-02-09 | 新日本製鐵株式会社 | マンドレルミルにおけるマンドレル引抜法 |
| WO2017038656A1 (ja) * | 2015-08-28 | 2017-03-09 | 日本臓器製薬株式会社 | 新規な４－ベンゾアゾニン誘導体の製造方法 |
-
1978
- 1978-07-28 JP JP9233678A patent/JPS5536403A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5536403A (en) | 1980-03-14 |
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