SU1039445A3 - Способ получени производных циклофосфатиазенового р да - Google Patents
Способ получени производных циклофосфатиазенового р да Download PDFInfo
- Publication number
- SU1039445A3 SU1039445A3 SU802940708A SU2940708A SU1039445A3 SU 1039445 A3 SU1039445 A3 SU 1039445A3 SU 802940708 A SU802940708 A SU 802940708A SU 2940708 A SU2940708 A SU 2940708A SU 1039445 A3 SU1039445 A3 SU 1039445A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- strong
- medium
- aziridine
- compound
- formula
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title claims 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 19
- 125000004069 aziridinyl group Chemical group 0.000 claims abstract description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 30
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 claims description 9
- -1 chloro, phenyl Chemical group 0.000 claims description 7
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- 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 claims description 5
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- OZDGMOYKSFPLSE-UHFFFAOYSA-N 2-Methylaziridine Chemical compound CC1CN1 OZDGMOYKSFPLSE-UHFFFAOYSA-N 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 238000002955 isolation Methods 0.000 claims description 2
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 239000003814 drug Substances 0.000 abstract 1
- 238000002347 injection Methods 0.000 description 16
- 239000007924 injection Substances 0.000 description 16
- 239000000243 solution Substances 0.000 description 12
- 206010028980 Neoplasm Diseases 0.000 description 11
- 239000000047 product Substances 0.000 description 9
- 238000000034 method Methods 0.000 description 8
- 230000000259 anti-tumor effect Effects 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 241000699670 Mus sp. Species 0.000 description 5
- 239000000460 chlorine Chemical group 0.000 description 5
- 229910052801 chlorine Inorganic materials 0.000 description 5
- 238000001819 mass spectrum Methods 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 238000000921 elemental analysis Methods 0.000 description 4
- 208000008342 Leukemia P388 Diseases 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 238000002329 infrared spectrum Methods 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001541 aziridines Chemical class 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- 239000002674 ointment Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000829 suppository Substances 0.000 description 2
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 1
- XLJQPXVBQNJNLW-UHFFFAOYSA-N 1-methylaziridine Chemical compound CN1CC1 XLJQPXVBQNJNLW-UHFFFAOYSA-N 0.000 description 1
- GMTAOJMPNXLKJI-UHFFFAOYSA-N 2-[[1-cyclopentyl-5-[1-(oxetan-3-yl)piperidin-4-yl]pyrazol-3-yl]amino]pyridine-4-carbonitrile Chemical compound C1(CCCC1)N1N=C(C=C1C1CCN(CC1)C1COC1)NC=1C=C(C#N)C=CN=1 GMTAOJMPNXLKJI-UHFFFAOYSA-N 0.000 description 1
- 201000009030 Carcinoma Diseases 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 102100028971 HLA class I histocompatibility antigen, C alpha chain Human genes 0.000 description 1
- 101100395312 Homo sapiens HLA-C gene Proteins 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 206010039491 Sarcoma Diseases 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 239000000824 cytostatic agent Substances 0.000 description 1
- 230000001085 cytostatic effect Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- UYMKPFRHYYNDTL-UHFFFAOYSA-N ethenamine Chemical compound NC=C UYMKPFRHYYNDTL-UHFFFAOYSA-N 0.000 description 1
- 235000010228 ethyl p-hydroxybenzoate Nutrition 0.000 description 1
- 239000004403 ethyl p-hydroxybenzoate Substances 0.000 description 1
- 229940043351 ethyl-p-hydroxybenzoate Drugs 0.000 description 1
- NUVBSKCKDOMJSU-UHFFFAOYSA-N ethylparaben Chemical compound CCOC(=O)C1=CC=C(O)C=C1 NUVBSKCKDOMJSU-UHFFFAOYSA-N 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 231100000086 high toxicity Toxicity 0.000 description 1
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 1
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 201000001441 melanoma Diseases 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- FEPJGKIDZJBOOX-UHFFFAOYSA-N morpholin-4-ium;phenoxide Chemical compound C1COCC[NH2+]1.[O-]C1=CC=CC=C1 FEPJGKIDZJBOOX-UHFFFAOYSA-N 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 230000035772 mutation Effects 0.000 description 1
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000000149 penetrating effect Effects 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 239000008213 purified water Substances 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 230000036299 sexual function Effects 0.000 description 1
- 239000010802 sludge Substances 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 238000002255 vaccination Methods 0.000 description 1
- 231100000925 very toxic Toxicity 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000003871 white petrolatum 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
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6581—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and nitrogen atoms with or without oxygen or sulfur atoms, as ring hetero atoms
- C07F9/6587—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and nitrogen atoms with or without oxygen or sulfur atoms, as ring hetero atoms having two phosphorus atoms as ring hetero atoms in the same ring
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Glass Compositions (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
- Lubricants (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7917336A FR2460303A1 (fr) | 1979-07-04 | 1979-07-04 | Nouveaux composes a cycle inorganique utiles comme medicaments et procede pour leur preparation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU1039445A3 true SU1039445A3 (ru) | 1983-08-30 |
Family
ID=9227493
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU802940708A SU1039445A3 (ru) | 1979-07-04 | 1980-07-01 | Способ получени производных циклофосфатиазенового р да |
Country Status (17)
| Country | Link |
|---|---|
| US (2) | US4317773A (cg-RX-API-DMAC10.html) |
| EP (1) | EP0022407B1 (cg-RX-API-DMAC10.html) |
| JP (1) | JPS5686192A (cg-RX-API-DMAC10.html) |
| AT (1) | ATE879T1 (cg-RX-API-DMAC10.html) |
| AU (1) | AU535125B2 (cg-RX-API-DMAC10.html) |
| CA (1) | CA1149399A (cg-RX-API-DMAC10.html) |
| DE (1) | DE3060305D1 (cg-RX-API-DMAC10.html) |
| DK (1) | DK287580A (cg-RX-API-DMAC10.html) |
| ES (1) | ES8104813A1 (cg-RX-API-DMAC10.html) |
| FR (1) | FR2460303A1 (cg-RX-API-DMAC10.html) |
| GR (1) | GR69190B (cg-RX-API-DMAC10.html) |
| HU (1) | HU185616B (cg-RX-API-DMAC10.html) |
| IE (1) | IE49924B1 (cg-RX-API-DMAC10.html) |
| IL (1) | IL60383A0 (cg-RX-API-DMAC10.html) |
| NZ (1) | NZ194229A (cg-RX-API-DMAC10.html) |
| PT (1) | PT71488A (cg-RX-API-DMAC10.html) |
| SU (1) | SU1039445A3 (cg-RX-API-DMAC10.html) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2460303A1 (fr) * | 1979-07-04 | 1981-01-23 | Anvar | Nouveaux composes a cycle inorganique utiles comme medicaments et procede pour leur preparation |
| FR2536751B1 (fr) * | 1982-11-25 | 1986-04-25 | Centre Nat Rech Scient | Nouveaux derives de tricyclophosphazenes, procede pour leur preparation et leur application en tant que medicament |
| US7721999B2 (en) * | 2005-05-20 | 2010-05-25 | The Boeing Company | Aerospace vehicle fairing systems and associated methods |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2460303A1 (fr) * | 1979-07-04 | 1981-01-23 | Anvar | Nouveaux composes a cycle inorganique utiles comme medicaments et procede pour leur preparation |
-
1979
- 1979-07-04 FR FR7917336A patent/FR2460303A1/fr active Pending
-
1980
- 1980-06-24 IL IL60383A patent/IL60383A0/xx unknown
- 1980-06-24 IE IE1308/80A patent/IE49924B1/en unknown
- 1980-06-25 US US06/162,759 patent/US4317773A/en not_active Expired - Lifetime
- 1980-06-26 CA CA000354877A patent/CA1149399A/en not_active Expired
- 1980-06-30 AU AU59776/80A patent/AU535125B2/en not_active Expired - Fee Related
- 1980-07-01 SU SU802940708A patent/SU1039445A3/ru active
- 1980-07-02 DE DE8080401002T patent/DE3060305D1/de not_active Expired
- 1980-07-02 EP EP80401002A patent/EP0022407B1/fr not_active Expired
- 1980-07-02 AT AT80401002T patent/ATE879T1/de active
- 1980-07-03 ES ES493454A patent/ES8104813A1/es not_active Expired
- 1980-07-03 NZ NZ194229A patent/NZ194229A/xx unknown
- 1980-07-03 PT PT71488A patent/PT71488A/pt unknown
- 1980-07-03 DK DK287580A patent/DK287580A/da not_active Application Discontinuation
- 1980-07-03 HU HU801657A patent/HU185616B/hu unknown
- 1980-07-04 JP JP9215980A patent/JPS5686192A/ja active Pending
- 1980-07-04 GR GR62367A patent/GR69190B/el unknown
-
1981
- 1981-09-09 US US06/300,561 patent/US4469687A/en not_active Expired - Fee Related
Non-Patent Citations (1)
| Title |
|---|
| 1. Гамбицкий П.А. и др. Хими этиленимина, 1966, с. 76-84, 191194. 2,Eurppean JournaE of Cancer., J.-F. Babarre и др.Antitvunour Activity of Some Cyc ophosphazenes, Vot, 15, 5, p. 637-64.3, 1979 (май). 3.Rec. Trav. Chim. (Nether6ands), 91, 935-941, 1972. * |
Also Published As
| Publication number | Publication date |
|---|---|
| ATE879T1 (de) | 1982-05-15 |
| DE3060305D1 (en) | 1982-06-03 |
| ES493454A0 (es) | 1981-05-16 |
| DK287580A (da) | 1981-01-05 |
| JPS5686192A (en) | 1981-07-13 |
| GR69190B (cg-RX-API-DMAC10.html) | 1982-05-06 |
| IE49924B1 (en) | 1986-01-08 |
| IE801308L (en) | 1981-01-04 |
| HU185616B (en) | 1985-03-28 |
| PT71488A (en) | 1980-08-01 |
| ES8104813A1 (es) | 1981-05-16 |
| US4317773A (en) | 1982-03-02 |
| EP0022407B1 (fr) | 1982-04-21 |
| FR2460303A1 (fr) | 1981-01-23 |
| AU535125B2 (en) | 1984-03-01 |
| NZ194229A (en) | 1983-02-15 |
| IL60383A0 (en) | 1980-09-16 |
| EP0022407A1 (fr) | 1981-01-14 |
| US4469687A (en) | 1984-09-04 |
| AU5977680A (en) | 1981-01-15 |
| CA1149399A (en) | 1983-07-05 |
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