CS196381B2 - Method of producing unsaturated derivatives of 7-acylamido-3-cephem-4-carboxylic acid - Google Patents
Method of producing unsaturated derivatives of 7-acylamido-3-cephem-4-carboxylic acid Download PDFInfo
- Publication number
- CS196381B2 CS196381B2 CS775327A CS532777A CS196381B2 CS 196381 B2 CS196381 B2 CS 196381B2 CS 775327 A CS775327 A CS 775327A CS 532777 A CS532777 A CS 532777A CS 196381 B2 CS196381 B2 CS 196381B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- group
- alkyl
- formula
- compounds
- benzyl
- Prior art date
Links
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims abstract description 3
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims abstract 4
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 125000003277 amino group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 3
- 125000004432 carbon atom Chemical group C* 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims 2
- -1 alkaline earth metal carbonates Chemical class 0.000 claims 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
- 150000007529 inorganic bases Chemical class 0.000 claims 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims 1
- BWLUMTFWVZZZND-UHFFFAOYSA-N Dibenzylamine Chemical compound C=1C=CC=CC=1CNCC1=CC=CC=C1 BWLUMTFWVZZZND-UHFFFAOYSA-N 0.000 claims 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 1
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 claims 1
- 239000004472 Lysine Substances 0.000 claims 1
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims 1
- HTLZVHNRZJPSMI-UHFFFAOYSA-N N-ethylpiperidine Chemical compound CCN1CCCCC1 HTLZVHNRZJPSMI-UHFFFAOYSA-N 0.000 claims 1
- MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 claims 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 1
- JVVXZOOGOGPDRZ-SLFFLAALSA-N [(1R,4aS,10aR)-1,4a-dimethyl-7-propan-2-yl-2,3,4,9,10,10a-hexahydrophenanthren-1-yl]methanamine Chemical compound NC[C@]1(C)CCC[C@]2(C)C3=CC=C(C(C)C)C=C3CC[C@H]21 JVVXZOOGOGPDRZ-SLFFLAALSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 239000003513 alkali Substances 0.000 claims 1
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical class [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 230000000844 anti-bacterial effect Effects 0.000 claims 1
- UPABQMWFWCMOFV-UHFFFAOYSA-N benethamine Chemical compound C=1C=CC=CC=1CNCCC1=CC=CC=C1 UPABQMWFWCMOFV-UHFFFAOYSA-N 0.000 claims 1
- JUHORIMYRDESRB-UHFFFAOYSA-N benzathine Chemical compound C=1C=CC=CC=1CNCCNCC1=CC=CC=C1 JUHORIMYRDESRB-UHFFFAOYSA-N 0.000 claims 1
- 229910052791 calcium Inorganic materials 0.000 claims 1
- 239000011575 calcium Substances 0.000 claims 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 230000002503 metabolic effect Effects 0.000 claims 1
- 239000002207 metabolite Substances 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 229910052700 potassium Inorganic materials 0.000 claims 1
- 239000011591 potassium Substances 0.000 claims 1
- 239000002243 precursor Substances 0.000 claims 1
- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 claims 1
- 229960004919 procaine Drugs 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- 208000015181 infectious disease Diseases 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 244000005700 microbiome Species 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D501/14—Compounds having a nitrogen atom directly attached in position 7
- C07D501/16—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3
- C07D501/20—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids
- C07D501/24—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids with hydrocarbon radicals, substituted by hetero atoms or hetero rings, attached in position 3
- C07D501/26—Methylene radicals, substituted by oxygen atoms; Lactones thereof with the 2-carboxyl group
- C07D501/28—Methylene radicals, substituted by oxygen atoms; Lactones thereof with the 2-carboxyl group with the 7-amino radical acylated by an aliphatic carboxylic acid, which is substituted by hetero atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
- C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/60—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton with the carbon atom of at least one of the carboxyl groups bound to nitrogen atoms
-
- 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
- C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D501/14—Compounds having a nitrogen atom directly attached in position 7
- C07D501/16—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3
- C07D501/20—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids
- C07D501/24—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids with hydrocarbon radicals, substituted by hetero atoms or hetero rings, attached in position 3
- C07D501/36—Methylene radicals, substituted by sulfur atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Cephalosporin Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
NANNINI GIULIANO, PERRONE ETTORE, BRESSO, SEVERINO DINO, VEDASCQ DI STRESA, MEINARDI GIUSEPPE, MONTI GISELLA, BIANCHI ALBERTA, FORGIONE ANGELO, MILÁN a
CONFALONIERI CARLO, CUSAŇO MILANINO (Itálie)
FARMITALIA CARLO ERBA S.p.A., MILÁN (Itálie) (54) Způsob výroby nenasycených derivátů kyseliny 7-acylamido-3-cefem-4-karbcxylové
Vynález se týká způsobu výroby nenasycených derivátů kyseliny 7-acylamido-3-’Cefem-4-karboxylové obecného vzorce I ve kterém R značí atom vodíku nebo methyl, nebo
X Z-A-S-CH.-C-NH—T A H o > o
X (I)
ve kterém.
Z značí kyanovou nebo karbamoylovou skupinu, ·
A značí skupinu transrCH=CH— , cis-CH=CH— nebo —C^C— ,
В značí skupinu vzorce —О—С—СНз nebo —S—Het,
II o
ve kterém Heit představuje skupinu obecného vzorce
ve které Ri a R2 se nezávisle na sobě volí ze skupiny zahrnující atom vodíku a methyl, а X značí volnou karboxylovou skupinu nebo esiterifikovanou karboxylovou skupinu vzorce —COOM, v němž M značí skupinu —CH—O—C—R4 ' -I II.
R3O nebo —CH2—Q—C—O—R3 ,
III.
RžO
198381 v nichž R3 značí atom vodíku nebo Ci-6alkyl, Q je atom kyslíku nebo skupina —NH—,
R4 značí Ci_6alkyl nebo zásaditou skupinu, zejména С1_6а1ку1 nebo Ct-sarýlCi-taikyl, substituovanou alespoň jednou aminoskupinou, která je popřípadě substituovaná, například Rá je
Ci_6alkyl-NH—CH3,
C6_earylCi-6alkyl-NH—CH3,
Ci _éalkyl ,
nebo . —CHz—NHz, Rs značí Ci-talkyl, C6_8aryl, C4-.gcykloalkyl, heteromonocyklický kruh, jako- je pyridyl, heterobicykllcký -kruh, jako je indanyl, nebo Có-sarylCi_6alkyl, jako je benzyl.
Claims (1)
- Předmětem vynálezu - - jsou - rovněž farmaceuticky nebo veterinárně vhodné soli sloučenin obecného vzorce I, ve kterém X .značí karboxylovou skupinu, a rovněž antlbakteriálně účinné . metabolity a metabolické prekursory sloučenin obecného vzorce I.Jako- farmaceuticky a veterinárně vhodných solí sloučenin obecného vzorce I lze použít buď solí s anorganickými bázemi, jako například s hydroxidem· sodným, draselným, vápenatým nebo hlinitým, nebo- s uhličitany nebo kyselými uhličitany alkalických kovů a kovů alkalických zemin, nebo- - solí s anorganickými bázemi, jako například s organickými aminy, -například s lysinem, triethylaminem, prokainem, dibenzylaminem, N-benzyl-já-fenethylaminem, N,N‘-dibenzylethylendiamlnem, . dehydroabietylaminem, N-ethylpiperidinem, diethanolaminem, N-methylgluka.minem, -tris-hydí^c^xymethylaminomethanem a podobnými.Představuje-li X esterifikovanou karboxylovou skupinu, je touto skupinou výhod ně skupina - -obecného vzorce —COOM, ve kterém- M značí radikály obecných vzorcůCH—O—C—RiR3 O nebo· —CHz—Q—'C—O—Rs ,Rz O ve kterých R3 - představuje atom vodíku nebo alkyl s 1—6 atomy uhlíku, Q značí —O— nebo —NH—, Ri značí alkylovou skupinu s 1—6 atomy uhlíku nebo bazickou skupinu, zvláště alkylovou skupinu s- 1—6 atomy uhlíku nebo C6.-Jary1C1_6a1ky1fSku^pinu (například -benzylovou skupinu) - substituovanou alespoň jednou aminoskupínou, která může být -bud nesubstituovaná, nebo substituovaná, -například Ri představuje -skupinu -Ci-6alkyl-NH— CH3, - C6_»ayylCi_6alky--NH—CH3 Cl —6Alkyl 1 —CHzNHz, a - Rs značí - alkylovou - skupinu s 1 až 6 - atomy - uhlíku, například methyl, propyl nebo- isopropyl, 06-8ary1ovou skupinu, zvláště fenyl, C^-scykloalkylovou skupinu, zvláště cyklopentyl, cyklohexyl nebo cykloheptyl, heteromonocyklický - kruh, například - pyridyl, heterobicykllcký kruh, například - indanyl, a- C,^-(^s^ir^l^l^i-^-alkylovou skupinu, například benzyl.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS784991A CS196382B2 (cs) | 1977-02-11 | 1978-07-27 | Způsob výroby nenasycených derivátů kyseliny 7-acylamido-3-cefem-4-karboxylove |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT20173/77A IT1075277B (it) | 1977-02-11 | 1977-02-11 | Derivati insaturi e epossidici dell'acio 7-acilamido-3-cefem-4-carbossilico e procedimento per la loro preparazione |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS196381B2 true CS196381B2 (en) | 1980-03-31 |
Family
ID=11164407
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS775327A CS196381B2 (en) | 1977-02-11 | 1977-08-11 | Method of producing unsaturated derivatives of 7-acylamido-3-cephem-4-carboxylic acid |
| CS788042A CS199714B2 (en) | 1977-02-11 | 1978-01-17 | Process for preparing heteromonocyclic and heterobicyclic derivatives of unsaturated 7-acylamido-3-cephem-4-carboxylic acids |
| CS78331A CS199713B2 (en) | 1977-02-11 | 1978-01-17 | Process for preparing heteromonocyclic and heterobicyclic derivatives of unsaturated 7-acylamido-3-cephem-4-carboxylic acid |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS788042A CS199714B2 (en) | 1977-02-11 | 1978-01-17 | Process for preparing heteromonocyclic and heterobicyclic derivatives of unsaturated 7-acylamido-3-cephem-4-carboxylic acids |
| CS78331A CS199713B2 (en) | 1977-02-11 | 1978-01-17 | Process for preparing heteromonocyclic and heterobicyclic derivatives of unsaturated 7-acylamido-3-cephem-4-carboxylic acid |
Country Status (29)
| Country | Link |
|---|---|
| US (3) | US4154830A (cs) |
| JP (2) | JPS5398991A (cs) |
| AT (2) | AT355206B (cs) |
| AU (2) | AU512934B2 (cs) |
| BE (2) | BE858433A (cs) |
| CA (2) | CA1103237A (cs) |
| CH (3) | CH632513A5 (cs) |
| CS (3) | CS196381B2 (cs) |
| CY (1) | CY1234A (cs) |
| DE (2) | DE2736471A1 (cs) |
| DK (2) | DK155944C (cs) |
| FI (3) | FI65259C (cs) |
| FR (3) | FR2380285A1 (cs) |
| GB (4) | GB1582295A (cs) |
| GR (2) | GR71901B (cs) |
| HK (1) | HK55284A (cs) |
| HU (2) | HU177596B (cs) |
| IL (3) | IL52708A0 (cs) |
| IT (1) | IT1075277B (cs) |
| MY (1) | MY8500446A (cs) |
| NL (2) | NL7708943A (cs) |
| NO (4) | NO152654C (cs) |
| NZ (2) | NZ184889A (cs) |
| PH (1) | PH16946A (cs) |
| SE (4) | SE7709002L (cs) |
| SG (1) | SG9484G (cs) |
| SU (4) | SU845788A3 (cs) |
| YU (1) | YU40307B (cs) |
| ZA (2) | ZA774835B (cs) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1075277B (it) * | 1977-02-11 | 1985-04-22 | Erba Carlo Spa | Derivati insaturi e epossidici dell'acio 7-acilamido-3-cefem-4-carbossilico e procedimento per la loro preparazione |
| JPS5593413A (en) * | 1979-01-11 | 1980-07-15 | Osaka Gas Co Ltd | Lining method for inner surface of pipe |
| US4331666A (en) * | 1979-05-11 | 1982-05-25 | Farmitalia Carlo Erba S.P.A. | 3-[(8-Carboxy-6-tetrazolo[1,5-b]pyridazinyl)-thiomethyl]-7-[2-(2-amino-4-thiazolyl)-2-methoxyimino-acetamido]-3-cephem-4-carboxylic acid |
| US4420477A (en) * | 1979-11-30 | 1983-12-13 | Fujisawa Pharmaceutical Co., Ltd. | Cephem compounds |
| US4405617A (en) * | 1980-02-11 | 1983-09-20 | Fujisawa Pharmaceutical Co., Ltd. | 3-(Propynyltetrazol)thiomethyl-3-cephems |
| GB2076803B (en) * | 1980-05-16 | 1984-02-08 | Erba Farmitalia | Substituted 7-(a-oxy-imino-acetamido)-cephalosporins and process for their preparation |
| GB2186875A (en) * | 1983-10-31 | 1987-08-26 | Fujisawa Pharmaceutical Co | New cephem compounds and processes for preparation thereof |
| EP0225634B1 (en) * | 1985-12-13 | 1994-04-06 | Takeda Chemical Industries, Ltd. | Antibacterial compounds, their production and use |
| US5126349A (en) * | 1990-01-12 | 1992-06-30 | The Dow Chemical Company | Composition and use of substituted 3-thio-2-propynenitriles as an industrial antimicrobial |
| US5198445A (en) * | 1990-01-12 | 1993-03-30 | The Dow Chemical Company | Composition and use of substituted 3-thio-2-propynenitriles as industrial antimicrobials |
| WO1991011503A1 (en) * | 1990-01-12 | 1991-08-08 | The Dow Chemical Company | Composition and use of substituted 3-thio-2-propynenitriles as an industrial antimicrobial |
| US5157051A (en) * | 1992-03-05 | 1992-10-20 | The Dow Chemical Company | Composition and use of 3-thiocyano-2-halo-2-propenenitriles as antimicrobial agents |
| US5155119A (en) * | 1992-03-05 | 1992-10-13 | The Dow Chemical Company | 3-(2-pyridinylthio)-N-oxide, 2-halo-2-propenenitrile compounds useful as antimicrobials |
| US5206227A (en) * | 1992-06-02 | 1993-04-27 | The Dow Chemical Company | Composition and use of phosphonic acid, (2-halo-2-cyanoethenyl)-dialkyl esters as antimicrobials |
| JP3115455B2 (ja) * | 1992-12-18 | 2000-12-04 | 明治製菓株式会社 | 新規セファロスポリン誘導体 |
| SE9802974D0 (sv) * | 1998-09-03 | 1998-09-03 | Astra Ab | New crystalline forms |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1075277B (it) * | 1977-02-11 | 1985-04-22 | Erba Carlo Spa | Derivati insaturi e epossidici dell'acio 7-acilamido-3-cefem-4-carbossilico e procedimento per la loro preparazione |
| GB1478055A (en) * | 1973-07-27 | 1977-06-29 | Erba Carlo Spa | Cephalosporin compounds |
| US3883520A (en) * | 1973-08-17 | 1975-05-13 | Smithkline Corp | Substituted mercaptoacetamidocephalosporins |
| FI761035A7 (cs) * | 1975-04-21 | 1976-10-22 | Erba Carlo Spa | |
| ZA767084B (en) * | 1975-12-16 | 1977-10-26 | Erba Carlo Spa | Thiadiazolyl derivatives of 7-acylamido 3-cephem-4-carboxylic acid and process for their preparation |
| US4057631A (en) * | 1976-09-02 | 1977-11-08 | Smithkline Corporation | 7-(α-Substituted phenylacetamido)-3-(1-carboxymethylthioethyltetrazolyl-5-thiomethyl)-3-cephem-4-carboxylic acids |
| US4079134A (en) * | 1976-09-24 | 1978-03-14 | Smithkline Corporation | 7-Acylamino-3-(5-sulfomethyl-1,3,4-thiadiazol-2-ylthiomethyl)-3-cephem-4-carboxylic acids |
-
1977
- 1977-02-11 IT IT20173/77A patent/IT1075277B/it active
- 1977-08-08 DK DK353577A patent/DK155944C/da not_active IP Right Cessation
- 1977-08-08 NO NO772779A patent/NO152654C/no unknown
- 1977-08-08 US US05/822,638 patent/US4154830A/en not_active Expired - Lifetime
- 1977-08-09 SE SE7709002A patent/SE7709002L/xx not_active Application Discontinuation
- 1977-08-09 CY CY1234A patent/CY1234A/xx unknown
- 1977-08-09 GB GB33418/77A patent/GB1582295A/en not_active Expired
- 1977-08-09 GB GB43324/79A patent/GB1590610A/en not_active Expired
- 1977-08-10 ZA ZA00774835A patent/ZA774835B/xx unknown
- 1977-08-10 FI FI772411A patent/FI65259C/fi not_active IP Right Cessation
- 1977-08-10 HU HU77EA176A patent/HU177596B/hu not_active IP Right Cessation
- 1977-08-10 NZ NZ184889A patent/NZ184889A/xx unknown
- 1977-08-10 CA CA284,460A patent/CA1103237A/en not_active Expired
- 1977-08-11 CS CS775327A patent/CS196381B2/cs unknown
- 1977-08-11 CH CH984577A patent/CH632513A5/de not_active IP Right Cessation
- 1977-08-11 GR GR54135A patent/GR71901B/el unknown
- 1977-08-11 AT AT585677A patent/AT355206B/de not_active IP Right Cessation
- 1977-08-12 NL NL7708943A patent/NL7708943A/xx not_active Application Discontinuation
- 1977-08-12 DE DE19772736471 patent/DE2736471A1/de active Granted
- 1977-08-12 AU AU27865/77A patent/AU512934B2/en not_active Expired
- 1977-08-12 IL IL52708A patent/IL52708A0/xx not_active IP Right Cessation
- 1977-08-12 FR FR7724952A patent/FR2380285A1/fr active Granted
- 1977-08-13 JP JP9742077A patent/JPS5398991A/ja active Granted
- 1977-08-22 SU SU772516753A patent/SU845788A3/ru active
- 1977-09-06 YU YU2109/77A patent/YU40307B/xx unknown
- 1977-09-06 BE BE180695A patent/BE858433A/xx not_active IP Right Cessation
-
1978
- 1978-01-09 NO NO780074A patent/NO780074L/no unknown
- 1978-01-10 DK DK11578A patent/DK11578A/da not_active Application Discontinuation
- 1978-01-11 GB GB4691/80A patent/GB1597262A/en not_active Expired
- 1978-01-11 ZA ZA00780181A patent/ZA78181B/xx unknown
- 1978-01-11 SE SE7800292A patent/SE7800292L/xx unknown
- 1978-01-11 GB GB1121/78A patent/GB1597261A/en not_active Expired
- 1978-01-11 US US05/868,665 patent/US4172892A/en not_active Expired - Lifetime
- 1978-01-12 HU HU78EA182A patent/HU178918B/hu unknown
- 1978-01-13 NL NL7800443A patent/NL7800443A/xx not_active Application Discontinuation
- 1978-01-16 AU AU32476/78A patent/AU513444B2/en not_active Expired
- 1978-01-16 DE DE19782801644 patent/DE2801644A1/de not_active Withdrawn
- 1978-01-17 CS CS788042A patent/CS199714B2/cs unknown
- 1978-01-17 NZ NZ186236A patent/NZ186236A/xx unknown
- 1978-01-17 CS CS78331A patent/CS199713B2/cs unknown
- 1978-01-17 AT AT32778A patent/AT356270B/de not_active IP Right Cessation
- 1978-01-17 IL IL53830A patent/IL53830A/xx unknown
- 1978-01-19 GR GR55208A patent/GR72589B/el unknown
- 1978-01-20 PH PH20693A patent/PH16946A/en unknown
- 1978-01-24 FR FR7801928A patent/FR2384783A1/fr active Granted
- 1978-01-26 JP JP676978A patent/JPS53121788A/ja active Pending
- 1978-02-03 BE BE184877A patent/BE863625A/xx not_active IP Right Cessation
- 1978-02-10 SU SU782578100A patent/SU856388A3/ru active
- 1978-02-10 FI FI780437A patent/FI780437A7/fi not_active Application Discontinuation
- 1978-02-10 CH CH153278A patent/CH636359A5/de not_active IP Right Cessation
- 1978-02-10 FI FI800994A patent/FI800994A7/fi not_active Application Discontinuation
- 1978-02-10 CA CA296,689A patent/CA1108603A/en not_active Expired
- 1978-07-28 SU SU782640405A patent/SU753361A3/ru active
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1979
- 1979-04-26 SU SU792759905A patent/SU904524A3/ru active
- 1979-12-14 NO NO794101A patent/NO794101L/no unknown
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1980
- 1980-01-08 SE SE8000110A patent/SE446536B/sv not_active IP Right Cessation
- 1980-01-24 CH CH58280A patent/CH634330A5/de not_active IP Right Cessation
- 1980-01-31 NO NO800239A patent/NO800239L/no unknown
- 1980-03-05 IL IL59527A patent/IL59527A0/xx unknown
- 1980-03-07 FR FR8005220A patent/FR2445834A1/fr active Granted
- 1980-04-18 SE SE8002904A patent/SE8002904L/sv not_active Application Discontinuation
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1981
- 1981-08-21 US US06/295,074 patent/US4388314A/en not_active Expired - Fee Related
-
1984
- 1984-02-06 SG SG94/84A patent/SG9484G/en unknown
- 1984-07-19 HK HK552/84A patent/HK55284A/xx unknown
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1985
- 1985-12-30 MY MY446/85A patent/MY8500446A/xx unknown
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