HU182801B - Process for preparing n-substituted aziridine-2-carboxylic acid derivatives - Google Patents
Process for preparing n-substituted aziridine-2-carboxylic acid derivatives Download PDFInfo
- Publication number
- HU182801B HU182801B HU80383A HU38380A HU182801B HU 182801 B HU182801 B HU 182801B HU 80383 A HU80383 A HU 80383A HU 38380 A HU38380 A HU 38380A HU 182801 B HU182801 B HU 182801B
- Authority
- HU
- Hungary
- Prior art keywords
- cyano
- formula
- aziridine
- compound
- group
- Prior art date
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- WBGBOXYJYPVLQJ-UHFFFAOYSA-N aziridine-2-carboxylic acid Chemical class OC(=O)C1CN1 WBGBOXYJYPVLQJ-UHFFFAOYSA-N 0.000 title description 3
- 238000004519 manufacturing process Methods 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 43
- 239000000243 solution Substances 0.000 claims description 30
- -1 N-substituted aziridine-2-carboxylic acid Chemical class 0.000 claims description 17
- 238000002360 preparation method Methods 0.000 claims description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
- 239000004480 active ingredient Substances 0.000 claims description 13
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 13
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 12
- WIIZWVCIJKGZOK-RKDXNWHRSA-N chloramphenicol Chemical compound ClC(Cl)C(=O)N[C@H](CO)[C@H](O)C1=CC=C([N+]([O-])=O)C=C1 WIIZWVCIJKGZOK-RKDXNWHRSA-N 0.000 claims description 11
- 229960005091 chloramphenicol Drugs 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 11
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
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- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
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- ARRIEYYNOLTVTE-UHFFFAOYSA-N 2,3-dibromopropanenitrile Chemical compound BrCC(Br)C#N ARRIEYYNOLTVTE-UHFFFAOYSA-N 0.000 description 5
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- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
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- 230000008018 melting Effects 0.000 description 4
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 4
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- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
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- 150000002894 organic compounds Chemical class 0.000 description 1
- 150000002960 penicillins Chemical class 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
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- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 235000003441 saturated fatty acids Nutrition 0.000 description 1
- 150000004671 saturated fatty acids Chemical class 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
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- 239000003765 sweetening agent Substances 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
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- 231100000331 toxic Toxicity 0.000 description 1
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- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D203/00—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom
- C07D203/04—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D203/06—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D203/22—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms directly attached to the ring nitrogen atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Immunology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Transplantation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19792906603 DE2906603A1 (de) | 1979-02-21 | 1979-02-21 | N-substituierte aziridin-2-carbonsaeurederivate, verfahren zu deren herstellung sowie diese substanzen enthaltende arzneimittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HU182801B true HU182801B (en) | 1984-03-28 |
Family
ID=6063481
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU80383A HU182801B (en) | 1979-02-21 | 1980-02-19 | Process for preparing n-substituted aziridine-2-carboxylic acid derivatives |
Country Status (19)
| Country | Link |
|---|---|
| US (2) | US4397848A (en, 2012) |
| EP (1) | EP0014976B1 (en, 2012) |
| JP (1) | JPS55113760A (en, 2012) |
| AR (1) | AR223863A1 (en, 2012) |
| AT (1) | ATE818T1 (en, 2012) |
| AU (1) | AU529982B2 (en, 2012) |
| CA (1) | CA1148962A (en, 2012) |
| CS (1) | CS208798B2 (en, 2012) |
| DD (1) | DD148772A5 (en, 2012) |
| DE (2) | DE2906603A1 (en, 2012) |
| ES (1) | ES488656A1 (en, 2012) |
| FI (1) | FI70702C (en, 2012) |
| HU (1) | HU182801B (en, 2012) |
| IE (1) | IE49267B1 (en, 2012) |
| IL (1) | IL59425A (en, 2012) |
| PL (1) | PL129707B1 (en, 2012) |
| PT (1) | PT70847A (en, 2012) |
| SU (1) | SU1181541A3 (en, 2012) |
| ZA (1) | ZA80902B (en, 2012) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4925835A (en) * | 1986-05-01 | 1990-05-15 | Sloan-Kettering Institute For Cancer Research | Aziridinyl putrescine containing compositions and their uses in treating prostate cancer |
| JPH07301287A (ja) * | 1995-03-23 | 1995-11-14 | Sumitomo Heavy Ind Ltd | 制御装置に用いられる内接噛合遊星歯車機構 |
| AU8171498A (en) * | 1997-06-27 | 1999-01-19 | Arizona Board Of Regents On Behalf Of The University Of Arizona, The | Novel cyanoaziridines for treating cancer |
| WO2002041871A2 (en) * | 2000-11-21 | 2002-05-30 | Board Of Regents, The University Of Texas System | Composition comprising an imexon or derivatives thereof and lipids |
| US20030129222A1 (en) * | 2000-11-21 | 2003-07-10 | Gabriel Lopez-Berestein | Liposomal imexon |
| JP2005531495A (ja) * | 2001-12-21 | 2005-10-20 | シャイア ラボラトリーズ，インコーポレイテッド | 高い物理的安定性を有する経口カプセル製剤 |
| US20040005339A1 (en) * | 2002-06-28 | 2004-01-08 | Shojaei Amir H. | Formulations of fenofibrate and/or fenofibrate derivatives with improved oral bioavailability |
| HRP20050696B1 (en) | 2003-01-14 | 2008-10-31 | Arena Pharmaceuticals Inc. | 1,2,3-trisubstituted aryl and heteroaryl derivatives as modulators of metabolism and the prpphylaxis and treatment of disorders related thereto such as diabetes and hyperglycemia |
| DK1606282T3 (da) * | 2003-02-24 | 2009-03-16 | Arena Pharm Inc | Phenyl- og pyridylpipereidinye-derivater som modulatorer af glucosemetabolisme |
| AR045047A1 (es) | 2003-07-11 | 2005-10-12 | Arena Pharm Inc | Derivados arilo y heteroarilo trisustituidos como moduladores del metabolismo y de la profilaxis y tratamiento de desordenes relacionados con los mismos |
| EA011671B1 (ru) * | 2004-06-04 | 2009-04-28 | Арена Фармасьютикалз, Инк. | Замещенные производные арила и гетероарила в качестве модуляторов метаболизма и для профилактики и лечения связанных с ним расстройств |
| DOP2006000010A (es) | 2005-01-10 | 2006-07-31 | Arena Pharm Inc | Procedimiento para preparar eteres aromáticos |
| MY148521A (en) * | 2005-01-10 | 2013-04-30 | Arena Pharm Inc | Substituted pyridinyl and pyrimidinyl derivatives as modulators of metabolism and the treatment of disorders related thereto |
| GEP20104966B (en) * | 2005-09-16 | 2010-04-26 | Arena Pharm Inc | Modulators of metabolism and the treatment of disorders related thereto |
| TW200811140A (en) * | 2006-07-06 | 2008-03-01 | Arena Pharm Inc | Modulators of metabolism and the treatment of disorders related thereto |
| TW200811147A (en) * | 2006-07-06 | 2008-03-01 | Arena Pharm Inc | Modulators of metabolism and the treatment of disorders related thereto |
| CA2786994C (en) | 2010-01-27 | 2018-01-16 | Arena Pharmaceuticals, Inc. | Processes for the preparation of (r)-2-(7-(4-cyclopentyl-3-(trifluoromethyl)benzyloxy)-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetic acid and salts thereof |
| US10894787B2 (en) | 2010-09-22 | 2021-01-19 | Arena Pharmaceuticals, Inc. | Modulators of the GPR119 receptor and the treatment of disorders related thereto |
| EP4445956A3 (en) | 2015-01-06 | 2024-12-04 | Arena Pharmaceuticals, Inc. | Compound for use in treating conditions related to the s1p1 receptor |
| PT3310760T (pt) | 2015-06-22 | 2022-11-10 | Arena Pharm Inc | Sal cristalino de l-arginina de ácido (r)-2-(7-(4-ciclopentil-3-(trifluorometil)benziloxi)-1,2,3,4-tetrahidrociclo-penta[b]indol-3-il)acético para utilização em distúrbios associados a recetores de s1p1 |
| CA3053418A1 (en) | 2017-02-16 | 2018-08-23 | Arena Pharmaceuticals, Inc. | Compounds and methods for treatment of primary biliary cholangitis |
| KR20210029190A (ko) | 2018-06-06 | 2021-03-15 | 아레나 파마슈티칼스, 인크. | S1p1 수용체와 관련된 병태의 치료 방법 |
| CN113816887A (zh) * | 2021-08-31 | 2021-12-21 | 华中科技大学 | 一种氮杂环丙烷类化合物及其制备方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2644820A1 (de) * | 1976-10-05 | 1978-04-06 | Boehringer Mannheim Gmbh | Cancerostatisch und immunstimulierend wirkende 1-(n-acyl-carbamoyl)-2-cyanaziridine sowie verfahren zur herstellung derselben |
| DE2731264A1 (de) | 1977-07-11 | 1979-02-01 | Boehringer Mannheim Gmbh | Neue 1-acyl-2-cyanaziridine, verfahren zu deren herstellung und diese verbindungen enthaltende pharmazeutische zubereitungen |
-
1979
- 1979-02-21 DE DE19792906603 patent/DE2906603A1/de not_active Withdrawn
-
1980
- 1980-02-15 ES ES488656A patent/ES488656A1/es not_active Expired
- 1980-02-16 DE DE8080100792T patent/DE3060268D1/de not_active Expired
- 1980-02-16 AT AT80100792T patent/ATE818T1/de not_active IP Right Cessation
- 1980-02-16 EP EP80100792A patent/EP0014976B1/de not_active Expired
- 1980-02-18 ZA ZA00800902A patent/ZA80902B/xx unknown
- 1980-02-18 SU SU802882348A patent/SU1181541A3/ru active
- 1980-02-18 PL PL1980222088A patent/PL129707B1/pl unknown
- 1980-02-18 CA CA000345886A patent/CA1148962A/en not_active Expired
- 1980-02-18 AU AU55649/80A patent/AU529982B2/en not_active Ceased
- 1980-02-19 DD DD80219137A patent/DD148772A5/de not_active IP Right Cessation
- 1980-02-19 HU HU80383A patent/HU182801B/hu not_active IP Right Cessation
- 1980-02-19 CS CS801134A patent/CS208798B2/cs unknown
- 1980-02-19 IL IL59425A patent/IL59425A/xx unknown
- 1980-02-20 PT PT70847A patent/PT70847A/pt unknown
- 1980-02-20 IE IE327/80A patent/IE49267B1/en unknown
- 1980-02-20 FI FI800510A patent/FI70702C/fi not_active IP Right Cessation
- 1980-02-21 JP JP1977580A patent/JPS55113760A/ja active Granted
-
1981
- 1981-02-15 AR AR279976A patent/AR223863A1/es active
- 1981-02-20 US US06/236,375 patent/US4397848A/en not_active Expired - Fee Related
-
1983
- 1983-05-17 US US06/495,548 patent/US4517183A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| SU1181541A3 (ru) | 1985-09-23 |
| IE49267B1 (en) | 1985-09-04 |
| DE2906603A1 (de) | 1980-09-04 |
| IL59425A (en) | 1984-05-31 |
| ES488656A1 (es) | 1980-09-16 |
| JPS55113760A (en) | 1980-09-02 |
| ZA80902B (en) | 1981-03-25 |
| FI800510A7 (fi) | 1980-08-22 |
| EP0014976A1 (de) | 1980-09-03 |
| IL59425A0 (en) | 1980-05-30 |
| FI70702B (fi) | 1986-06-26 |
| DE3060268D1 (en) | 1982-05-19 |
| EP0014976B1 (de) | 1982-04-07 |
| PL222088A1 (en, 2012) | 1980-12-01 |
| US4517183A (en) | 1985-05-14 |
| CA1148962A (en) | 1983-06-28 |
| FI70702C (fi) | 1986-10-06 |
| PT70847A (de) | 1980-03-01 |
| AR223863A1 (es) | 1981-09-30 |
| AU5564980A (en) | 1980-08-28 |
| IE800327L (en) | 1980-08-21 |
| CS208798B2 (en) | 1981-09-15 |
| ATE818T1 (de) | 1982-04-15 |
| JPH0150700B2 (en, 2012) | 1989-10-31 |
| US4397848A (en) | 1983-08-09 |
| AU529982B2 (en) | 1983-06-30 |
| DD148772A5 (de) | 1981-06-10 |
| PL129707B1 (en) | 1984-06-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| HU90 | Patent valid on 900628 | ||
| HMM4 | Cancellation of final prot. due to non-payment of fee |