JPH0442395B2 - - Google Patents
Info
- Publication number
- JPH0442395B2 JPH0442395B2 JP4641786A JP4641786A JPH0442395B2 JP H0442395 B2 JPH0442395 B2 JP H0442395B2 JP 4641786 A JP4641786 A JP 4641786A JP 4641786 A JP4641786 A JP 4641786A JP H0442395 B2 JPH0442395 B2 JP H0442395B2
- Authority
- JP
- Japan
- Prior art keywords
- thieno
- tetrahydro
- pyridine
- chloro
- benzyl
- 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
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 30
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 16
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 7
- 239000012279 sodium borohydride Substances 0.000 claims description 7
- 229910000033 sodium borohydride Inorganic materials 0.000 claims description 7
- ARHVQOBKFAPHQP-UHFFFAOYSA-N (2-chlorophenyl)-(6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl)methanone Chemical compound ClC1=CC=CC=C1C(=O)N1CC(C=CS2)=C2CC1 ARHVQOBKFAPHQP-UHFFFAOYSA-N 0.000 claims description 6
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 6
- 230000002378 acidificating effect Effects 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 4
- 229940098779 methanesulfonic acid Drugs 0.000 claims description 3
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 claims description 2
- 229940092714 benzenesulfonic acid Drugs 0.000 claims description 2
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- -1 lithium aluminum hydride Chemical compound 0.000 description 10
- 238000000034 method Methods 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 7
- 239000000047 product Substances 0.000 description 6
- 239000012280 lithium aluminium hydride Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- 238000000921 elemental analysis Methods 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 239000003638 chemical reducing agent Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- DBDCNCCRPKTRSD-UHFFFAOYSA-N thieno[3,2-b]pyridine Chemical class C1=CC=C2SC=CC2=N1 DBDCNCCRPKTRSD-UHFFFAOYSA-N 0.000 description 2
- PHWBOXQYWZNQIN-UHFFFAOYSA-N ticlopidine Chemical compound ClC1=CC=CC=C1CN1CC(C=CS2)=C2CC1 PHWBOXQYWZNQIN-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- KDDNKZCVYQDGKE-UHFFFAOYSA-N (2-chlorophenyl)methanamine Chemical compound NCC1=CC=CC=C1Cl KDDNKZCVYQDGKE-UHFFFAOYSA-N 0.000 description 1
- ZHJTZFCCKYYGJK-UHFFFAOYSA-N 2-[(2-chlorophenyl)methyl]-4,5,6,7-tetrahydrothieno[3,2-c]pyridine Chemical compound ClC1=CC=CC=C1CC(S1)=CC2=C1CCNC2 ZHJTZFCCKYYGJK-UHFFFAOYSA-N 0.000 description 1
- HLPRKWVEMYDPAU-UHFFFAOYSA-N 2-thiophen-2-ylethyl 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OCCC1=CC=CS1 HLPRKWVEMYDPAU-UHFFFAOYSA-N 0.000 description 1
- RBIGKSZIQCTIJF-UHFFFAOYSA-N 3-formylthiophene Chemical compound O=CC=1C=CSC=1 RBIGKSZIQCTIJF-UHFFFAOYSA-N 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 150000002366 halogen compounds Chemical class 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- MKYRMMMSZSVIGD-UHFFFAOYSA-N thieno[3,2-c]pyridine Chemical compound N1=CC=C2SC=CC2=C1 MKYRMMMSZSVIGD-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4641786A JPS62205087A (ja) | 1986-03-05 | 1986-03-05 | チクロピジンの製造方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4641786A JPS62205087A (ja) | 1986-03-05 | 1986-03-05 | チクロピジンの製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS62205087A JPS62205087A (ja) | 1987-09-09 |
| JPH0442395B2 true JPH0442395B2 (cs) | 1992-07-13 |
Family
ID=12746572
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP4641786A Granted JPS62205087A (ja) | 1986-03-05 | 1986-03-05 | チクロピジンの製造方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS62205087A (cs) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6043368A (en) * | 1996-09-04 | 2000-03-28 | Poli Industria Chimica, S.P.A. | Method of making thieno-pyridine derivatives |
-
1986
- 1986-03-05 JP JP4641786A patent/JPS62205087A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS62205087A (ja) | 1987-09-09 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2000063334A (ja) | エンイン誘導体の新規製造中間体及びその製造法 | |
| JPH0442395B2 (cs) | ||
| DE69902071T2 (de) | Verfahren zur Herstellung von 2-substituierten Pyridinen | |
| JPS5949221B2 (ja) | ３−アシルアミノ−４−ホモイソツイスタンの製造法 | |
| JPH04243875A (ja) | ２−フェニル−６−（ピリミジン−２−イル）ピリジン化合物の製造方法、中間体化合物及び中間体化合物の製造方法 | |
| KR101195631B1 (ko) | ９-［２-(포스포노메톡시)에틸］아데닌의 개선된 제조방법 | |
| JPH059435B2 (cs) | ||
| JPH0442394B2 (cs) | ||
| JPH08208591A (ja) | ２−アミノベンゼンスルホン酸誘導体ならびに２−アミノベンゼンスルホニルクロリド誘導体とその製造法およびその合成中間体としての使用 | |
| JPS6232188B2 (cs) | ||
| CN106256818B (zh) | 一种带三氟甲硫基的茚酮和其衍生物及其制备方法 | |
| JPH0440354B2 (cs) | ||
| CA1208233A (en) | Intermediates for the preparation of 4-phenyl-1,3- benzodiazepins and methods for preparing the intermediates | |
| KR100856133B1 (ko) | 아토르바스타틴의 개선된 제조방법 | |
| JP2767295B2 (ja) | インドール―３―カルボニトリル化合物の製造方法 | |
| JPS62103088A (ja) | ４，５，６，７−テトラヒドロチエノ〔３，２−ｃ〕ピリジン又はその塩の製造方法 | |
| KR820000786B1 (ko) | 우라실 유도체의 제조법 | |
| GB1579541A (en) | Process for the production of (1,1 - dithien - (3)-yl - 1 - hydroxy - (3) - propyl) - (1-phenyl - 1 - hydroxy - (2) - propyl)-amine and (1,1 - dithien - (3) - yl-(1) - propen - (3) - yl) - (1 - phenyl-1 - hydroxy - (2) - propyl)- amine | |
| JP6466109B2 (ja) | ２−ベンジルオキシ−５−（トリフルオロメチル）ピリミジン誘導体及びその製造方法 | |
| JPS6346057B2 (cs) | ||
| JPH0959293A (ja) | ２位炭素鎖置換アデノシン誘導体の製造法 | |
| JPH02256680A (ja) | ５―（２―クロロベンジル）―４，５，６，７―テトラヒドロチエノ〔３，２―ｃ〕ピリジン又はその塩の製造方法 | |
| JP2003040823A (ja) | フロログルシド類の製造方法 | |
| JPS63208557A (ja) | 四級アンモニウム塩 | |
| JPH101451A (ja) | ３，４−ジヒドロキシベンツアルデヒド又は３−アルキルオキシ−４−ヒドロキシベンツアルデヒドの製造方法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EXPY | Cancellation because of completion of term |