CA1282073C - Process for producing thiotepa - Google Patents
Process for producing thiotepaInfo
- Publication number
- CA1282073C CA1282073C CA000588625A CA588625A CA1282073C CA 1282073 C CA1282073 C CA 1282073C CA 000588625 A CA000588625 A CA 000588625A CA 588625 A CA588625 A CA 588625A CA 1282073 C CA1282073 C CA 1282073C
- Authority
- CA
- Canada
- Prior art keywords
- haloethylamine
- beta
- thiotepa
- producing
- process according
- 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 - Fee Related
Links
- 238000000034 method Methods 0.000 title claims abstract description 7
- FOCVUCIESVLUNU-UHFFFAOYSA-N Thiotepa Chemical compound C1CN1P(N1CC1)(=S)N1CC1 FOCVUCIESVLUNU-UHFFFAOYSA-N 0.000 title claims abstract description 6
- 229960001196 thiotepa Drugs 0.000 title claims abstract description 5
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 claims abstract description 5
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
- 238000003756 stirring Methods 0.000 claims description 5
- 239000007864 aqueous solution Substances 0.000 claims description 4
- 239000011541 reaction mixture Substances 0.000 claims description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims description 2
- 229910000288 alkali metal carbonate Inorganic materials 0.000 claims description 2
- 150000008041 alkali metal carbonates Chemical class 0.000 claims description 2
- VKPPFDPXZWFDFA-UHFFFAOYSA-N 2-chloroethanamine Chemical group NCCCl VKPPFDPXZWFDFA-UHFFFAOYSA-N 0.000 claims 1
- DIOZLZOUTWUWIQ-UHFFFAOYSA-N 2-iodoethanamine Chemical group NCCI DIOZLZOUTWUWIQ-UHFFFAOYSA-N 0.000 claims 1
- 150000004820 halides Chemical class 0.000 claims 1
- 238000010952 in-situ formation Methods 0.000 claims 1
- 230000003472 neutralizing effect Effects 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 238000011065 in-situ storage Methods 0.000 abstract description 2
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000000370 acceptor Substances 0.000 description 3
- -1 thiophos-phoryl halide Chemical class 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- NUMXHEUHHRTBQT-AATRIKPKSA-N 2,4-dimethoxy-1-[(e)-2-nitroethenyl]benzene Chemical compound COC1=CC=C(\C=C\[N+]([O-])=O)C(OC)=C1 NUMXHEUHHRTBQT-AATRIKPKSA-N 0.000 description 1
- IZQAUUVBKYXMET-UHFFFAOYSA-N 2-bromoethanamine Chemical compound NCCBr IZQAUUVBKYXMET-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 241001163743 Perlodes Species 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 241000534944 Thia Species 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 231100000481 chemical toxicant Toxicity 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000001475 halogen functional group Chemical group 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 235000014786 phosphorus Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 239000003440 toxic substance Substances 0.000 description 1
Classifications
-
- 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
- C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
- C07F9/564—Three-membered rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Biochemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Cephalosporin Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/146,511 US4918199A (en) | 1988-01-21 | 1988-01-21 | Process for producing thiotepa |
| US07/146,511 | 1988-01-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1282073C true CA1282073C (en) | 1991-03-26 |
Family
ID=22517714
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000588625A Expired - Fee Related CA1282073C (en) | 1988-01-21 | 1989-01-19 | Process for producing thiotepa |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US4918199A (OSRAM) |
| EP (1) | EP0324920B1 (OSRAM) |
| JP (1) | JPH021496A (OSRAM) |
| KR (1) | KR0135608B1 (OSRAM) |
| AT (1) | ATE111474T1 (OSRAM) |
| CA (1) | CA1282073C (OSRAM) |
| DE (1) | DE3851523T2 (OSRAM) |
| ES (1) | ES2059474T3 (OSRAM) |
| FI (1) | FI90776C (OSRAM) |
| IL (1) | IL88453A (OSRAM) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7024367B2 (en) * | 2000-02-18 | 2006-04-04 | Matsushita Electric Industrial Co., Ltd. | Biometric measuring system with detachable announcement device |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5561121A (en) * | 1993-11-09 | 1996-10-01 | American Cyanamid Company | Stable lyophilized thiotepa composition |
| CN108484669B (zh) * | 2018-06-01 | 2020-07-07 | 黑龙江福和制药集团股份有限公司 | 塞替派的制备方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2212146A (en) * | 1939-03-10 | 1940-08-20 | Du Pont | Preparation of alpha-alkylenimines, e. g., ethylenimine |
| US2670347A (en) * | 1952-01-08 | 1954-02-23 | American Cyanamid Co | Thiophosphoric acid derivatives and method of preparing the same |
-
1988
- 1988-01-21 US US07/146,511 patent/US4918199A/en not_active Expired - Lifetime
- 1988-11-22 IL IL88453A patent/IL88453A/xx not_active IP Right Cessation
- 1988-11-23 AT AT88119469T patent/ATE111474T1/de not_active IP Right Cessation
- 1988-11-23 ES ES88119469T patent/ES2059474T3/es not_active Expired - Lifetime
- 1988-11-23 DE DE3851523T patent/DE3851523T2/de not_active Expired - Fee Related
- 1988-11-23 EP EP88119469A patent/EP0324920B1/en not_active Expired - Lifetime
- 1988-12-26 KR KR1019880017532A patent/KR0135608B1/ko not_active Expired - Fee Related
-
1989
- 1989-01-18 JP JP1007904A patent/JPH021496A/ja active Granted
- 1989-01-19 CA CA000588625A patent/CA1282073C/en not_active Expired - Fee Related
- 1989-01-20 FI FI890309A patent/FI90776C/fi not_active IP Right Cessation
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7024367B2 (en) * | 2000-02-18 | 2006-04-04 | Matsushita Electric Industrial Co., Ltd. | Biometric measuring system with detachable announcement device |
Also Published As
| Publication number | Publication date |
|---|---|
| US4918199A (en) | 1990-04-17 |
| FI890309L (fi) | 1989-07-22 |
| EP0324920A2 (en) | 1989-07-26 |
| KR890011898A (ko) | 1989-08-23 |
| IL88453A0 (en) | 1989-06-30 |
| JPH0579075B2 (OSRAM) | 1993-11-01 |
| DE3851523T2 (de) | 1995-03-16 |
| EP0324920B1 (en) | 1994-09-14 |
| FI890309A0 (fi) | 1989-01-20 |
| EP0324920A3 (en) | 1990-10-31 |
| KR0135608B1 (ko) | 1998-04-23 |
| FI90776C (fi) | 1994-03-25 |
| IL88453A (en) | 1993-01-14 |
| FI90776B (fi) | 1993-12-15 |
| DE3851523D1 (de) | 1994-10-20 |
| ATE111474T1 (de) | 1994-09-15 |
| JPH021496A (ja) | 1990-01-05 |
| ES2059474T3 (es) | 1994-11-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKLA | Lapsed |