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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- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
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- 239000003960 organic solvent Substances 0.000 description 1
- ORTFAQDWJHRMNX-UHFFFAOYSA-M oxidooxomethyl Chemical compound [O-][C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-M 0.000 description 1
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- 239000010452 phosphate Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 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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- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 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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- 230000001225 therapeutic effect Effects 0.000 description 1
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- 125000005424 tosyloxy group Chemical group S(=O)(=O)(C1=CC=C(C)C=C1)O* 0.000 description 1
- 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 (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 |
| DE69819192T2 (de) | 1997-06-27 | 2004-06-09 | Amplimed, Inc., Tucson | Neue cyanoaziridine zur behandlung von krebs |
| 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 |
| US7011846B2 (en) * | 2001-12-21 | 2006-03-14 | Shire Laboratories, Inc. | Oral capsule formulation with increased physical stability |
| US20040005339A1 (en) * | 2002-06-28 | 2004-01-08 | Shojaei Amir H. | Formulations of fenofibrate and/or fenofibrate derivatives with improved oral bioavailability |
| DK1599468T3 (da) | 2003-01-14 | 2008-02-04 | Arena Pharm Inc | 1,2,3-trisubstituerede aryl- og heteroarylderivater som modulatorer af metabolisme og forebyggelse og behandling af forstyrrelser forbundet dermed såsom diabetes og hyperglykæmi |
| DE602004017703D1 (de) * | 2003-02-24 | 2008-12-24 | Arena Pharm Inc | Phenyl- und pyridylpiperidinderivate als modulatoren des glucose-metabolismus |
| 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 |
| CN101870690A (zh) * | 2004-06-04 | 2010-10-27 | 艾尼纳制药公司 | 作为代谢调节剂的经取代芳基和杂芳基衍生物及其相关病症的预防和治疗 |
| 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 |
| CA2619093A1 (en) * | 2005-09-16 | 2007-03-29 | Arena Pharmaceuticals, 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 |
| TW200811140A (en) * | 2006-07-06 | 2008-03-01 | Arena Pharm Inc | Modulators of metabolism and the treatment of disorders related thereto |
| SG182610A1 (en) | 2010-01-27 | 2012-08-30 | Arena Pharm 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 |
| JP5941916B2 (ja) | 2010-09-22 | 2016-06-29 | アリーナ ファーマシューティカルズ， インコーポレイテッド | Ｇｐｒ１１９レセプターのモジュレーターおよびそれに関連する障害の処置 |
| ES2995737T3 (en) | 2015-01-06 | 2025-02-11 | Arena Pharm Inc | Compound for use in treating conditions related to the s1p1 receptor |
| US10301262B2 (en) | 2015-06-22 | 2019-05-28 | Arena Pharmaceuticals, Inc. | Crystalline L-arginine salt of (R)-2-(7-(4-cyclopentyl-3-(trifluoromethyl)benzyloxy)-1,2,3,4-tetrahydrocyclo-penta [b]indol-3-yl)acetic acid(Compund1) for use in SIPI receptor-associated disorders |
| AU2018220521A1 (en) | 2017-02-16 | 2019-09-05 | Arena Pharmaceuticals, Inc. | Compounds and methods for treatment of primary biliary cholangitis |
| ES2987794T3 (es) | 2018-06-06 | 2024-11-18 | Arena Pharm Inc | Procedimientos de tratamiento de afecciones relacionadas con el receptor S1P1 |
| 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 AT AT80100792T patent/ATE818T1/de not_active IP Right Cessation
- 1980-02-16 EP EP80100792A patent/EP0014976B1/de not_active Expired
- 1980-02-16 DE DE8080100792T patent/DE3060268D1/de not_active Expired
- 1980-02-18 CA CA000345886A patent/CA1148962A/en not_active Expired
- 1980-02-18 SU SU802882348A patent/SU1181541A3/ru active
- 1980-02-18 ZA ZA00800902A patent/ZA80902B/xx unknown
- 1980-02-18 PL PL1980222088A patent/PL129707B1/pl unknown
- 1980-02-18 AU AU55649/80A patent/AU529982B2/en not_active Ceased
- 1980-02-19 HU HU80383A patent/HU182801B/hu not_active IP Right Cessation
- 1980-02-19 IL IL59425A patent/IL59425A/xx unknown
- 1980-02-19 CS CS801134A patent/CS208798B2/cs unknown
- 1980-02-19 DD DD80219137A patent/DD148772A5/de not_active IP Right Cessation
- 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 |
|---|---|
| ES488656A1 (es) | 1980-09-16 |
| PT70847A (de) | 1980-03-01 |
| FI70702C (fi) | 1986-10-06 |
| DD148772A5 (de) | 1981-06-10 |
| US4517183A (en) | 1985-05-14 |
| PL129707B1 (en) | 1984-06-30 |
| IL59425A0 (en) | 1980-05-30 |
| DE3060268D1 (en) | 1982-05-19 |
| JPS55113760A (en) | 1980-09-02 |
| AU529982B2 (en) | 1983-06-30 |
| US4397848A (en) | 1983-08-09 |
| AU5564980A (en) | 1980-08-28 |
| JPH0150700B2 (en, 2012) | 1989-10-31 |
| FI70702B (fi) | 1986-06-26 |
| DE2906603A1 (de) | 1980-09-04 |
| AR223863A1 (es) | 1981-09-30 |
| IL59425A (en) | 1984-05-31 |
| CA1148962A (en) | 1983-06-28 |
| ATE818T1 (de) | 1982-04-15 |
| EP0014976B1 (de) | 1982-04-07 |
| IE49267B1 (en) | 1985-09-04 |
| ZA80902B (en) | 1981-03-25 |
| HU182801B (en) | 1984-03-28 |
| SU1181541A3 (ru) | 1985-09-23 |
| PL222088A1 (en, 2012) | 1980-12-01 |
| IE800327L (en) | 1980-08-21 |
| EP0014976A1 (de) | 1980-09-03 |
| FI800510A7 (fi) | 1980-08-22 |
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