DD246299A5 - Verfahren zur herstellung n-substituierter anziridin-2-carbonsaeurederivaten - Google Patents
Verfahren zur herstellung n-substituierter anziridin-2-carbonsaeurederivaten Download PDFInfo
- Publication number
- DD246299A5 DD246299A5 DD85284394A DD28439485A DD246299A5 DD 246299 A5 DD246299 A5 DD 246299A5 DD 85284394 A DD85284394 A DD 85284394A DD 28439485 A DD28439485 A DD 28439485A DD 246299 A5 DD246299 A5 DD 246299A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- compounds
- general formula
- methyl
- carboxylic acid
- pyridine
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 19
- 150000001875 compounds Chemical class 0.000 claims abstract description 57
- 238000002360 preparation method Methods 0.000 claims abstract description 12
- 230000008569 process Effects 0.000 claims abstract description 12
- 150000003839 salts Chemical class 0.000 claims abstract description 7
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 11
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 9
- 150000001204 N-oxides Chemical class 0.000 claims description 8
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 7
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 7
- 150000002825 nitriles Chemical group 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- KKFDJZZADQONDE-UHFFFAOYSA-N (hydridonitrato)hydroxidocarbon(.) Chemical compound O[C]=N KKFDJZZADQONDE-UHFFFAOYSA-N 0.000 claims description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 2
- -1 N-substituted aziridine-2-carboxylic acid Chemical class 0.000 abstract description 14
- 230000001506 immunosuppresive effect Effects 0.000 abstract description 8
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- 230000002519 immonomodulatory effect Effects 0.000 abstract description 6
- 239000000126 substance Substances 0.000 abstract description 6
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- 238000006243 chemical reaction Methods 0.000 description 19
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- ILVXOBCQQYKLDS-UHFFFAOYSA-N pyridine N-oxide Chemical compound [O-][N+]1=CC=CC=C1 ILVXOBCQQYKLDS-UHFFFAOYSA-N 0.000 description 8
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- 239000000370 acceptor Substances 0.000 description 1
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- 239000002671 adjuvant Substances 0.000 description 1
- 235000010419 agar Nutrition 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 230000000735 allogeneic effect Effects 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 150000001540 azides Chemical class 0.000 description 1
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- XGDRZDIAZMPNJZ-UHFFFAOYSA-J calcium;magnesium;octadecanoate;phosphate Chemical compound [Mg+2].[Ca+2].[O-]P([O-])([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XGDRZDIAZMPNJZ-UHFFFAOYSA-J 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 208000030499 combat disease Diseases 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000008139 complexing agent Substances 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 229930182912 cyclosporin Natural products 0.000 description 1
- 238000005695 dehalogenation reaction Methods 0.000 description 1
- 239000012024 dehydrating agents Substances 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- KQPGCIIYXNRIMU-UHFFFAOYSA-N ethyl 1-[(6-carbamoyl-2-methoxypyridin-3-yl)methyl]aziridine-2-carboxylate Chemical compound CCOC(=O)C1CN1CC1=CC=C(C(N)=O)N=C1OC KQPGCIIYXNRIMU-UHFFFAOYSA-N 0.000 description 1
- YDTYYHMUPMDXMB-UHFFFAOYSA-N ethyl 1-[(6-carbamoyl-2-oxo-1h-pyridin-3-yl)methyl]aziridine-2-carboxylate Chemical compound CCOC(=O)C1CN1CC1=CC=C(C(N)=O)NC1=O YDTYYHMUPMDXMB-UHFFFAOYSA-N 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 208000024908 graft versus host disease Diseases 0.000 description 1
- 210000000548 hind-foot Anatomy 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- RCBVKBFIWMOMHF-UHFFFAOYSA-L hydroxy-(hydroxy(dioxo)chromio)oxy-dioxochromium;pyridine Chemical compound C1=CC=NC=C1.C1=CC=NC=C1.O[Cr](=O)(=O)O[Cr](O)(=O)=O RCBVKBFIWMOMHF-UHFFFAOYSA-L 0.000 description 1
- 230000035874 hyperreactivity Effects 0.000 description 1
- 210000000987 immune system Anatomy 0.000 description 1
- 230000016784 immunoglobulin production Effects 0.000 description 1
- 230000004957 immunoregulator effect Effects 0.000 description 1
- 239000003018 immunosuppressive agent Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 230000000968 intestinal effect Effects 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 206010025135 lupus erythematosus Diseases 0.000 description 1
- 210000004698 lymphocyte Anatomy 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000002207 metabolite Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- KSXQRYUHBMAREL-UHFFFAOYSA-N methyl 3-methoxypyridine-2-carboxylate Chemical compound COC(=O)C1=NC=CC=C1OC KSXQRYUHBMAREL-UHFFFAOYSA-N 0.000 description 1
- PLAZZEMQCLWSSA-UHFFFAOYSA-N methyl 5-(aminomethyl)-6-methoxypyridine-2-carboxylate Chemical compound COC(=O)C1=CC=C(CN)C(OC)=N1 PLAZZEMQCLWSSA-UHFFFAOYSA-N 0.000 description 1
- QIDXRLXSKMXLJO-UHFFFAOYSA-N methyl 5-[(2-cyanoaziridin-1-yl)methyl]-6-methoxypyridine-2-carboxylate Chemical compound COC1=NC(C(=O)OC)=CC=C1CN1C(C#N)C1 QIDXRLXSKMXLJO-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 210000001616 monocyte Anatomy 0.000 description 1
- 201000006417 multiple sclerosis Diseases 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 125000002560 nitrile group Chemical group 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 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
- 210000000056 organ Anatomy 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- MMKQSIQNDMIVIN-UHFFFAOYSA-N oxido-(oxido(dioxo)chromio)oxy-dioxochromium;tetrabutylazanium Chemical compound [O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC.CCCC[N+](CCCC)(CCCC)CCCC MMKQSIQNDMIVIN-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 229940124531 pharmaceutical excipient Drugs 0.000 description 1
- 239000003444 phase transfer catalyst Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 238000006303 photolysis reaction Methods 0.000 description 1
- 230000015843 photosynthesis, light reaction Effects 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 206010039073 rheumatoid arthritis Diseases 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 1
- 206010043778 thyroiditis Diseases 0.000 description 1
- 238000002054 transplantation Methods 0.000 description 1
- 125000004954 trialkylamino group Chemical group 0.000 description 1
- 239000005051 trimethylchlorosilane Substances 0.000 description 1
- 235000019871 vegetable fat Nutrition 0.000 description 1
- 230000003313 weakening effect Effects 0.000 description 1
- 230000004584 weight gain Effects 0.000 description 1
- 235000019786 weight gain Nutrition 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Immunology (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Cephalosporin Compounds (AREA)
- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Medicines Containing Plant Substances (AREA)
- Pyridine Compounds (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Investigating Or Analysing Biological Materials (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19843446713 DE3446713A1 (de) | 1984-12-21 | 1984-12-21 | N-substituierte aziridin-2-carbonsaeurederivate, verfahren zu deren herstellung sowie diese substanzen enthaltende arzneimittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD246299A5 true DD246299A5 (de) | 1987-06-03 |
Family
ID=6253432
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD85284394A DD246299A5 (de) | 1984-12-21 | 1985-12-16 | Verfahren zur herstellung n-substituierter anziridin-2-carbonsaeurederivaten |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US4826858A (cs) |
| EP (1) | EP0186049B1 (cs) |
| JP (1) | JPS61152678A (cs) |
| CN (1) | CN85108698B (cs) |
| AT (1) | ATE54315T1 (cs) |
| AU (2) | AU578335B2 (cs) |
| CS (1) | CS256395B2 (cs) |
| DD (1) | DD246299A5 (cs) |
| DE (2) | DE3446713A1 (cs) |
| DK (1) | DK591685A (cs) |
| ES (1) | ES8800198A1 (cs) |
| FI (1) | FI854985A7 (cs) |
| GR (1) | GR853057B (cs) |
| HU (1) | HU194869B (cs) |
| IL (1) | IL77357A (cs) |
| NO (1) | NO855210L (cs) |
| NZ (1) | NZ214596A (cs) |
| PH (1) | PH23039A (cs) |
| PL (1) | PL148867B1 (cs) |
| PT (1) | PT81702B (cs) |
| SU (1) | SU1431676A3 (cs) |
| YU (1) | YU199985A (cs) |
| ZA (1) | ZA859592B (cs) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100738229B1 (ko) * | 2001-12-31 | 2007-07-12 | 한국화학연구원 | 신규한 피롤리디닐피리딘 유도체 |
| MXPA06006428A (es) * | 2003-12-12 | 2006-08-23 | Syngenta Participations Ag | Nuevos herbicidas. |
| MX2010013311A (es) | 2008-06-16 | 2010-12-21 | Hoffmann La Roche | Derivados de pirrolidina como antagonistas del receptor de nk2. |
| CN105272896A (zh) * | 2015-10-19 | 2016-01-27 | 山东国润生物医药有限公司 | (（2s）-2-氮丙啶基)二苯基甲醇的制备方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2833986A1 (de) * | 1978-08-03 | 1980-02-21 | Boehringer Mannheim Gmbh | Immunstimulierende n-substituierte aziridin-2-carbonsaeurederivate, verfahren zu ihrer herstellung sowie arzneimittel, die diese substanzen enthalten |
| DE3211254A1 (de) * | 1982-03-26 | 1983-09-29 | Boehringer Mannheim Gmbh, 6800 Mannheim | Verfahren zum nachweis des vorliegens einer allergie und zum spezifischen nachweis des fuer die allergie verantwortlichen allergens |
-
1984
- 1984-12-21 DE DE19843446713 patent/DE3446713A1/de not_active Withdrawn
-
1985
- 1985-12-11 AT AT85115785T patent/ATE54315T1/de not_active IP Right Cessation
- 1985-12-11 EP EP85115785A patent/EP0186049B1/de not_active Expired - Lifetime
- 1985-12-11 DE DE8585115785T patent/DE3578563D1/de not_active Expired - Lifetime
- 1985-12-16 PH PH33180A patent/PH23039A/en unknown
- 1985-12-16 FI FI854985A patent/FI854985A7/fi not_active Application Discontinuation
- 1985-12-16 DD DD85284394A patent/DD246299A5/de unknown
- 1985-12-16 AU AU51265/85A patent/AU578335B2/en not_active Ceased
- 1985-12-16 IL IL77357A patent/IL77357A/xx unknown
- 1985-12-17 JP JP60282177A patent/JPS61152678A/ja active Pending
- 1985-12-17 ZA ZA859592A patent/ZA859592B/xx unknown
- 1985-12-17 NZ NZ214596A patent/NZ214596A/xx unknown
- 1985-12-18 GR GR853057A patent/GR853057B/el unknown
- 1985-12-18 PT PT81702A patent/PT81702B/pt unknown
- 1985-12-18 DK DK591685A patent/DK591685A/da not_active Application Discontinuation
- 1985-12-19 YU YU01999/85A patent/YU199985A/xx unknown
- 1985-12-19 PL PL1985256941A patent/PL148867B1/pl unknown
- 1985-12-19 CS CS859547A patent/CS256395B2/cs unknown
- 1985-12-20 SU SU853991691A patent/SU1431676A3/ru active
- 1985-12-20 ES ES550285A patent/ES8800198A1/es not_active Expired
- 1985-12-20 NO NO855210A patent/NO855210L/no unknown
- 1985-12-20 HU HU854938A patent/HU194869B/hu unknown
- 1985-12-21 CN CN85108698A patent/CN85108698B/zh not_active Expired
-
1987
- 1987-11-25 US US07/125,353 patent/US4826858A/en not_active Expired - Fee Related
-
1990
- 1990-02-01 AU AU49015/90A patent/AU625355B2/en not_active Ceased
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