CS208798B2 - Method of making the new derivatives of the n-substituted aziridin-2-carboxyl acid - Google Patents
Method of making the new derivatives of the n-substituted aziridin-2-carboxyl acid Download PDFInfo
- Publication number
- CS208798B2 CS208798B2 CS801134A CS113480A CS208798B2 CS 208798 B2 CS208798 B2 CS 208798B2 CS 801134 A CS801134 A CS 801134A CS 113480 A CS113480 A CS 113480A CS 208798 B2 CS208798 B2 CS 208798B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- cyano
- group
- aziridine
- formula
- hal
- Prior art date
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- 239000002253 acid Substances 0.000 title description 7
- 238000004519 manufacturing process Methods 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 44
- -1 N-substituted aziridine-2-carboxylic acid Chemical class 0.000 claims description 14
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 11
- 238000002360 preparation method Methods 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 125000002560 nitrile group Chemical group 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 239000000543 intermediate Substances 0.000 claims description 2
- 238000002955 isolation Methods 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
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- 239000000706 filtrate Substances 0.000 description 11
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- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
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- 239000000741 silica gel Substances 0.000 description 9
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- 238000003756 stirring Methods 0.000 description 7
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- GDSNWDNQYWSZQR-UHFFFAOYSA-N 1-methoxyaziridine-2-carbonitrile Chemical compound CON1CC1C#N GDSNWDNQYWSZQR-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
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- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
- OYMQRTSYDQVPGI-UHFFFAOYSA-N 1-[(3-fluorophenyl)methoxy]aziridine-2-carbonitrile Chemical compound FC1=CC=CC(CON2C(C2)C#N)=C1 OYMQRTSYDQVPGI-UHFFFAOYSA-N 0.000 description 3
- SJFDGCBOMIAMIW-UHFFFAOYSA-N 1-butan-2-yloxyaziridine-2-carbonitrile Chemical compound CCC(C)ON1CC1C#N SJFDGCBOMIAMIW-UHFFFAOYSA-N 0.000 description 3
- ARRIEYYNOLTVTE-UHFFFAOYSA-N 2,3-dibromopropanenitrile Chemical compound BrCC(Br)C#N ARRIEYYNOLTVTE-UHFFFAOYSA-N 0.000 description 3
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- RFDXBINFEIBBHC-UHFFFAOYSA-N 1-(2-hydroxyethoxy)aziridine-2-carbonitrile Chemical compound OCCON1CC1C#N RFDXBINFEIBBHC-UHFFFAOYSA-N 0.000 description 2
- NOXPFQDJOJMZMD-UHFFFAOYSA-N 1-(2-phenoxyethoxy)aziridine-2-carbonitrile Chemical compound N#CC1CN1OCCOC1=CC=CC=C1 NOXPFQDJOJMZMD-UHFFFAOYSA-N 0.000 description 2
- VOCGFLKQAQIZPC-UHFFFAOYSA-N 1-(pyridin-2-ylmethoxy)aziridine-2-carbonitrile Chemical compound N#CC1CN1OCC1=CC=CC=N1 VOCGFLKQAQIZPC-UHFFFAOYSA-N 0.000 description 2
- VIJHSZAOZSRXFK-UHFFFAOYSA-N 1-(pyrimidin-2-ylmethoxy)aziridine-2-carbonitrile Chemical compound N#CC1CN1OCC1=NC=CC=N1 VIJHSZAOZSRXFK-UHFFFAOYSA-N 0.000 description 2
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- ORTFAQDWJHRMNX-UHFFFAOYSA-M oxidooxomethyl Chemical compound [O-][C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-M 0.000 description 1
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- XYKIUTSFQGXHOW-UHFFFAOYSA-N propan-2-one;toluene Chemical compound CC(C)=O.CC1=CC=CC=C1 XYKIUTSFQGXHOW-UHFFFAOYSA-N 0.000 description 1
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- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
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- 159000000000 sodium salts Chemical class 0.000 description 1
- IUTYMHORIFSPCU-UHFFFAOYSA-M sodium;1-ethoxyaziridine-2-carboxylate Chemical compound [Na+].CCON1CC1C([O-])=O IUTYMHORIFSPCU-UHFFFAOYSA-M 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
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- 235000019364 tetracycline Nutrition 0.000 description 1
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- 231100000419 toxicity 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)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Immunology (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Public Health (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 |
|---|---|
| CS208798B2 true CS208798B2 (en) | 1981-09-15 |
Family
ID=6063481
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS801134A CS208798B2 (en) | 1979-02-21 | 1980-02-19 | Method of making the new derivatives of the n-substituted aziridin-2-carboxyl acid |
Country Status (19)
| Country | Link |
|---|---|
| US (2) | US4397848A (pl) |
| EP (1) | EP0014976B1 (pl) |
| JP (1) | JPS55113760A (pl) |
| AR (1) | AR223863A1 (pl) |
| AT (1) | ATE818T1 (pl) |
| AU (1) | AU529982B2 (pl) |
| CA (1) | CA1148962A (pl) |
| CS (1) | CS208798B2 (pl) |
| DD (1) | DD148772A5 (pl) |
| DE (2) | DE2906603A1 (pl) |
| ES (1) | ES488656A1 (pl) |
| FI (1) | FI70702C (pl) |
| HU (1) | HU182801B (pl) |
| IE (1) | IE49267B1 (pl) |
| IL (1) | IL59425A (pl) |
| PL (1) | PL129707B1 (pl) |
| PT (1) | PT70847A (pl) |
| SU (1) | SU1181541A3 (pl) |
| ZA (1) | ZA80902B (pl) |
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 |
| ATE252381T1 (de) | 1997-06-27 | 2003-11-15 | Amplimed Inc | Neue cyanoaziridine zur behandlung von krebs |
| US20030129222A1 (en) * | 2000-11-21 | 2003-07-10 | Gabriel Lopez-Berestein | Liposomal imexon |
| 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 |
| 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 |
| AU2004205642C1 (en) | 2003-01-14 | 2012-01-12 | Arena Pharmaceuticals, Inc. | 1,2,3-trisubstituted aryl and heteroaryl derivatives as modulators of metabolism and the prophylaxis and treatment of disorders related thereto such as diabetes and hyperglycemia |
| KR20050106033A (ko) * | 2003-02-24 | 2005-11-08 | 아레나 파마슈티칼스, 인크. | 글루코스 대사 조절제로서의 페닐- 및피리딜피페리딘-유도체 |
| 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 |
| WO2005121121A2 (en) * | 2004-06-04 | 2005-12-22 | Arena Pharmaceuticals, Inc. | Substituted aryl and heteroaryl derivatives as modulators of metabolism and the prophylaxis and treatment of disorders related thereto |
| 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 |
| DOP2006000010A (es) | 2005-01-10 | 2006-07-31 | Arena Pharm Inc | Procedimiento para preparar eteres aromáticos |
| EP1931654B1 (en) * | 2005-09-16 | 2009-04-22 | Arena Pharmaceuticals, 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 |
| CA2812061A1 (en) | 2010-09-22 | 2012-03-29 | Arena Pharmaceuticals, Inc. | Modulators of the gpr119 receptor and the treatment of disorders related thereto |
| MX386419B (es) | 2015-01-06 | 2025-03-18 | Arena Pharm Inc | Metodos de condiciones de tratamiento relacionadas con el receptor s1p1. |
| MA42807A (fr) | 2015-06-22 | 2018-07-25 | Arena Pharm Inc | Sel l-arginine cristallin d'acide (r)-2-(7-(4-cyclopentyl-3-(trifluorométhyl)benzyloxy)-1,2,3,4-tétrahydrocyclo-penta[b]indol-3-yl)acétique (composé 1) pour une utilisation dans des troubles associés au récepteur de s1p1 |
| KR20190116416A (ko) | 2017-02-16 | 2019-10-14 | 아레나 파마슈티칼스, 인크. | 원발 담즙성 담관염을 치료하기 위한 화합물 및 방법 |
| KR102859841B1 (ko) | 2018-06-06 | 2025-09-12 | 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 EP EP80100792A patent/EP0014976B1/de not_active Expired
- 1980-02-16 AT AT80100792T patent/ATE818T1/de not_active IP Right Cessation
- 1980-02-18 SU SU802882348A patent/SU1181541A3/ru active
- 1980-02-18 PL PL1980222088A patent/PL129707B1/pl unknown
- 1980-02-18 AU AU55649/80A patent/AU529982B2/en not_active Ceased
- 1980-02-18 ZA ZA00800902A patent/ZA80902B/xx unknown
- 1980-02-18 CA CA000345886A patent/CA1148962A/en not_active Expired
- 1980-02-19 IL IL59425A patent/IL59425A/xx unknown
- 1980-02-19 HU HU80383A patent/HU182801B/hu not_active IP Right Cessation
- 1980-02-19 DD DD80219137A patent/DD148772A5/de not_active IP Right Cessation
- 1980-02-19 CS CS801134A patent/CS208798B2/cs unknown
- 1980-02-20 PT PT70847A patent/PT70847A/pt unknown
- 1980-02-20 FI FI800510A patent/FI70702C/fi not_active IP Right Cessation
- 1980-02-20 IE IE327/80A patent/IE49267B1/en unknown
- 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 |
|---|---|
| IL59425A (en) | 1984-05-31 |
| US4517183A (en) | 1985-05-14 |
| JPS55113760A (en) | 1980-09-02 |
| DE2906603A1 (de) | 1980-09-04 |
| EP0014976A1 (de) | 1980-09-03 |
| ATE818T1 (de) | 1982-04-15 |
| AU529982B2 (en) | 1983-06-30 |
| DD148772A5 (de) | 1981-06-10 |
| JPH0150700B2 (pl) | 1989-10-31 |
| PL129707B1 (en) | 1984-06-30 |
| IL59425A0 (en) | 1980-05-30 |
| PT70847A (de) | 1980-03-01 |
| DE3060268D1 (en) | 1982-05-19 |
| IE800327L (en) | 1980-08-21 |
| ZA80902B (en) | 1981-03-25 |
| IE49267B1 (en) | 1985-09-04 |
| AR223863A1 (es) | 1981-09-30 |
| FI70702C (fi) | 1986-10-06 |
| ES488656A1 (es) | 1980-09-16 |
| FI70702B (fi) | 1986-06-26 |
| FI800510A7 (fi) | 1980-08-22 |
| EP0014976B1 (de) | 1982-04-07 |
| SU1181541A3 (ru) | 1985-09-23 |
| HU182801B (en) | 1984-03-28 |
| PL222088A1 (pl) | 1980-12-01 |
| US4397848A (en) | 1983-08-09 |
| AU5564980A (en) | 1980-08-28 |
| CA1148962A (en) | 1983-06-28 |
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