SU576944A3 - Способ получени 6-/ -(аминоаминоалканоиламино)-арациламино/пенициллановых кислот или их солей - Google Patents
Способ получени 6-/ -(аминоаминоалканоиламино)-арациламино/пенициллановых кислот или их солейInfo
- Publication number
- SU576944A3 SU576944A3 SU7301949310A SU1949310A SU576944A3 SU 576944 A3 SU576944 A3 SU 576944A3 SU 7301949310 A SU7301949310 A SU 7301949310A SU 1949310 A SU1949310 A SU 1949310A SU 576944 A3 SU576944 A3 SU 576944A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- aracilamino
- amidinoaminoalkanoylamino
- salts
- preparing
- filtered
- Prior art date
Links
- 239000002253 acid Substances 0.000 title description 3
- 238000000034 method Methods 0.000 title description 2
- 150000003839 salts Chemical class 0.000 title description 2
- 150000007513 acids Chemical class 0.000 title 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 23
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- -1 AMIDINOAMINO Chemical class 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 238000002329 infrared spectrum Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000013067 intermediate product Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- VKPIRUPOWIICKO-UHFFFAOYSA-N 2-carbamimidoylbenzoyl chloride;hydrochloride Chemical compound Cl.NC(=N)C1=CC=CC=C1C(Cl)=O VKPIRUPOWIICKO-UHFFFAOYSA-N 0.000 description 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- BTJIUGUIPKRLHP-UHFFFAOYSA-N 4-nitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1 BTJIUGUIPKRLHP-UHFFFAOYSA-N 0.000 description 1
- 108010031086 Shiva-1 Proteins 0.000 description 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- AVKUERGKIZMTKX-NJBDSQKTSA-N ampicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CC=CC=C1 AVKUERGKIZMTKX-NJBDSQKTSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hcl hcl Chemical compound Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- RBKMMJSQKNKNEV-RITPCOANSA-N penicillanic acid Chemical compound OC(=O)[C@H]1C(C)(C)S[C@@H]2CC(=O)N21 RBKMMJSQKNKNEV-RITPCOANSA-N 0.000 description 1
- 210000003899 penis Anatomy 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000005301 thienylmethyl group Chemical group [H]C1=C([H])C([H])=C(S1)C([H])([H])* 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/33—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/335—Radicals substituted by nitrogen atoms not forming part of a nitro radical
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/52—Radicals substituted by nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/66—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/30—Hetero atoms other than halogen
- C07D333/36—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D499/00—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oncology (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Communicable Diseases (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
(54) СПОСОБ ПОЛУЧЕНИЯ 6- а- (АМИДИНОАМИНОАЛКАНСМ1ЛАМИНО) -АРАЦИЛАМИНО ПЕНИЦИЛЛАНОВЫХ присутствии дациклогексилкарбодиимида, когда X-СИ, или в присутствии алифатического третичного амина, например, триэтиламина или пиридина. когда X-С1, с последующим вьщелением продуктов в свободном виде или в виде соли. П р и м е р 1. 6 - D - 2 - Фенил - 2 (амидиноацетамидоацетамидо) - пеницилланова кислота., К 10 мл сухого диметилформамида при комнатной температуре в атмосфере азота добавл ют 810мг (бммолей) п - нитрофенола, 1,24 г (6 ммолей) дициклогексилкарбодиимида и 830 мг уксуснокислого аминогищ)охлорида, и полученную смесь перемецмвают в течение 2ч. О - а- амино- беизилпенициллин, триэтиламиновую соль в количестве 1,8 г (4 ммол ) добавл ют к желтой суспеизии и перемешивают при температуре окружающей среды в течение ночи. Затем твердое вещество отфильтровьшают, а чистый фильтрат ввод т в диэтиловьш эфир, количество которого составл ет 200 мл. Вьшавший в осадок желтый продукт отфильтровьшают и суспензируют в 100 мл метиленхлорида , к которому добавл ют 2 мл триэтиламина . Посла перемешивани в течение часа очищенный продукт отфильтровывают и подвергают вакуумной сушке. Выход составл ет 910 мг (степень конверсии 52,5%). ИК-спектр (мкм КВг) ; 3,0 (Ь); 3,4; 5,6; 6,0; 6,25; 6,6; 6,85; 7,15; 7,4; 8,1 и 8,85. Спектр ПМР (РРМ - фазово-импульсна модул ци ; DM SO-О); 1,48 (g, 6Н); 3,95 (с , 2Н) ; 4,04 (1Н); 5,2-5,8 (с,ЗН); 7,36 (7Н) и 8-9 (Ь ЗН). Пример 2. 6- D-2- Фенил - 2 - (3 . -амидинопропионамидо) ацетамидо пенищишанова кислота: К 1,35 г (3 ммол ) суспензии D а-аминобензшшенициллина , триэтиламиновой соли в 15 мл сухого диметилформамида в атмосфере азота добавл ют 0,63 мл (4,5 ммол ) триэтиламина и полученную смесь охлаждают в лед ной бане до 0°С. Добавл ют 770 мг (4,5 ммоль) амидинопропионилхлорид гидрохлорида и полученную смесь перемешивают при 0°С в течение 15 мин, а затем дополнительно в течение 1 ч при комнатной температуре . Далее смесь снова охлаждают до 0°С и дополнительно ввод т 237мг (1,5 ммоль) хлорид гидрохлоридной кислоты и 0,21 мл (1,5 ммолъ) триэтиламина и смесь перемешивают в течение 1 ч при комнатной температуре. После этого твердые вещества отфильтровывают, а фильтрат через капельницу ввод т при посто нном перемешивании в 200мл диэтилового эфира. 1,2 г сухого полупродукта суспензируют в 200 мл метиленхлорида и обрабатьшают 1 мл тризтиламина. После перемешивани в течение 30 мин чистый продукт отфильтровьгоают и сушат при пониженном давлении. Выход 640 мг (47,4% от теоретического выхода). ИК-спектр (мкм КВг) 3,0 (Ь); 3,35; 5,6; 6,0; 6, 6,6; 6,85; 7,15; 7,65; 8,0; 8,15 и 8,85. Спектр ПМР (РРМ; DMSO-Dg): 1,5 (g, 6Н); ,55 (b,4H); 4,0 (с, IH); 5,24-5,85 (с, ЗН); 1,4 7Н) и 9,0 (Ь, ЗН). - П р и м е р 3/ б -2 - {2 - Тиенил} - 2 - (N етиламидиноацетамидо ) j - пешщилланова кисота . В колбу емкостью 150 мл и имеюшую азотную подушку, загружают суспензию, состо щую из 3,55 г (0,01 мол ) DL -а- амино 2 тиенилметилпенищшлина в 70 мл сухого диметилформамида и 3,06 мл (0,022 мол ) триэткламина. Реакционную смесь охлаждают до 0°С и затем порционцо ввод т 1,88 г (0,11 мол ) N - метиламищшоацетилхлорид гидрохлорида. Полученную сушензию нагревают до комнатной температуры и выдер а1вают ири этой температуре в течение 1 ч. Затем смесь фильтруют, а чистый фильтрат через капельницу ввод т при быстром перемешивании в 1л диэтилоаого эфира. Полученную суспензию дополнительно перемешивают в течение 30 мин, отфильтровывают и твердый полупродукт сушат под вакуумом. Затем полупродукт суспенжруют в 100 МП метиленхлорида, к которому добавл ют 2мл триэтиламина. Через 45 мин чистый продукт отфильтровьшают и сушат при пониженном давлении . ЯМР (DMSO) + ); 1,5а,(6Н); 3,96 (S, Ш) 5,3-5,8 (с, ЗН) 7,4 (Ь 5Н) ИК-спектр (КВг): 3,0 (Ь) 5,62, 6,0-6,5 (Ь) 6,8, ,2/7,6,8,0,8,5,9,9,25. Пример 4. 6- D-2- Фенил - 2 - (п амидинобензамидо ) - ацетамидо - пеницилланова кислота. К суспензии, состо щей из 806 мг (1 ммоль) D- а - аминобензилпенициллинтригидрата в растворе, содержащем 10 мл сухого диметилформамида, 0,56 мл триэтилаламина; наход щейс под азотнсш подушкой и охлажденной в лед ной бане до 0°С, добавл ют через капельницу 438 мг (2 ммол ) п амидинобензоилхлорид гидрохлорида в 10 мл того же самого растворител . Полученный таким образом раствор перемешивают в течение 10 мин при 0°С, затем в течение 50 мин при комнатной температуре . Осадок, образовавшийс во врем реакции , отфильтровывают и чистый фильтрат добавл ют через капельницу в 400 мл диэтилового эфира при переме:шива1|йи. Продукт коричневато-желтого цвета очищаю суснендированием его в 30 мл метиленхлорида в присутствии 0,5 мл триэтиламина. После перемешивани в течение 1,5 ч продукт отфильтровьтают и подвергают вакуумной сушке. Выход составл ет 750 мг (75,5%). ЯМР (DMSO +D20) : 1,5 (g бН) 3,96 (с, 1Н) 5,3-5,8 (с, ЗН) 7,4 (ь 5Н), 8,0 (Ь 4Ш. ИК-спектр (КВг): 3,0 (Ь) 5,62,6,0-6.5 (Ь) 6,8, 7,2-7,6, 8,0. 8,5 8.9, 9г 9,25.. П р и м е р Э.6 - D - 2 - Фенил - 2 - (2 - имидазолиниладетамидо ) - аивтамйдо пеницилланова кислота.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US27706472A | 1972-08-02 | 1972-08-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU576944A3 true SU576944A3 (ru) | 1977-10-15 |
Family
ID=23059254
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU7301949310A SU576944A3 (ru) | 1972-08-02 | 1973-08-01 | Способ получени 6-/ -(аминоаминоалканоиламино)-арациламино/пенициллановых кислот или их солей |
| SU7502185959A SU576945A3 (ru) | 1972-08-02 | 1975-11-03 | Способ получени 6-/ -(имидоиламиноалкиллоиламино)арацициламино -пенициллановых кислот или их солей |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU7502185959A SU576945A3 (ru) | 1972-08-02 | 1975-11-03 | Способ получени 6-/ -(имидоиламиноалкиллоиламино)арацициламино -пенициллановых кислот или их солей |
Country Status (30)
| Country | Link |
|---|---|
| JP (1) | JPS5318039B2 (ru) |
| AR (1) | AR206879A1 (ru) |
| AT (1) | AT327382B (ru) |
| AU (1) | AU472676B2 (ru) |
| BE (1) | BE803094A (ru) |
| BG (1) | BG25798A3 (ru) |
| CA (1) | CA1015355A (ru) |
| CH (1) | CH574447A5 (ru) |
| CS (1) | CS168459B2 (ru) |
| DD (1) | DD106849A5 (ru) |
| DE (1) | DE2338389A1 (ru) |
| DK (1) | DK137047B (ru) |
| EG (1) | EG10896A (ru) |
| ES (1) | ES417461A1 (ru) |
| FI (1) | FI56840C (ru) |
| FR (1) | FR2194415B1 (ru) |
| GB (1) | GB1418656A (ru) |
| HU (1) | HU167653B (ru) |
| IE (1) | IE37961B1 (ru) |
| IL (1) | IL42820A (ru) |
| LU (1) | LU68143A1 (ru) |
| NL (1) | NL7310696A (ru) |
| NO (1) | NO144831C (ru) |
| PH (1) | PH12770A (ru) |
| PL (1) | PL96500B1 (ru) |
| RO (2) | RO63748A (ru) |
| SE (1) | SE415977B (ru) |
| SU (2) | SU576944A3 (ru) |
| YU (1) | YU36966B (ru) |
| ZA (1) | ZA735236B (ru) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4024130A (en) * | 1975-03-31 | 1977-05-17 | Pfizer Inc. | Process for the manufacture of alkali metal salts of 6-[2-phenyl-2-(imidoylaminoalkanoylamino)acetamido]penicillanic acids |
| US4073780A (en) * | 1976-06-03 | 1978-02-14 | Pfizer Inc. | 4-Pyridylformimidoylglycyl-D-phenylglycine |
-
1972
- 1972-12-27 GB GB5971172A patent/GB1418656A/en not_active Expired
-
1973
- 1973-01-01 AR AR249414A patent/AR206879A1/es active
- 1973-07-09 SE SE7309644A patent/SE415977B/xx unknown
- 1973-07-24 AU AU58433/73A patent/AU472676B2/en not_active Expired
- 1973-07-25 IL IL42820A patent/IL42820A/en unknown
- 1973-07-28 DE DE19732338389 patent/DE2338389A1/de not_active Withdrawn
- 1973-07-31 FR FR7327954A patent/FR2194415B1/fr not_active Expired
- 1973-07-31 IE IE1303/73A patent/IE37961B1/xx unknown
- 1973-07-31 CA CA177,719A patent/CA1015355A/en not_active Expired
- 1973-07-31 FI FI2405/73A patent/FI56840C/fi active
- 1973-08-01 BE BE1005272A patent/BE803094A/xx not_active IP Right Cessation
- 1973-08-01 ZA ZA735236A patent/ZA735236B/xx unknown
- 1973-08-01 SU SU7301949310A patent/SU576944A3/ru active
- 1973-08-01 NO NO3091/73A patent/NO144831C/no unknown
- 1973-08-01 YU YU2086/73A patent/YU36966B/xx unknown
- 1973-08-01 DD DD172673A patent/DD106849A5/xx unknown
- 1973-08-01 DK DK422873AA patent/DK137047B/da not_active IP Right Cessation
- 1973-08-01 ES ES417461A patent/ES417461A1/es not_active Expired
- 1973-08-01 HU HUPI392A patent/HU167653B/hu unknown
- 1973-08-02 RO RO7300075697A patent/RO63748A/ro unknown
- 1973-08-02 AT AT680773A patent/AT327382B/de active
- 1973-08-02 CH CH1124373A patent/CH574447A5/xx not_active IP Right Cessation
- 1973-08-02 RO RO7387460A patent/RO68719A2/ro unknown
- 1973-08-02 PL PL1973164483A patent/PL96500B1/pl unknown
- 1973-08-02 NL NL7310696A patent/NL7310696A/xx not_active Application Discontinuation
- 1973-08-02 EG EG298/73A patent/EG10896A/xx active
- 1973-08-02 CS CS5498A patent/CS168459B2/cs unknown
- 1973-08-02 BG BG024251A patent/BG25798A3/xx unknown
- 1973-08-02 JP JP8646073A patent/JPS5318039B2/ja not_active Expired
- 1973-08-02 LU LU68143A patent/LU68143A1/xx unknown
-
1975
- 1975-10-16 PH PH17666A patent/PH12770A/en unknown
- 1975-11-03 SU SU7502185959A patent/SU576945A3/ru active
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