IL40447A - Delta3-cephalosporin compounds and process for their preparation from delta2-cephalosporin - Google Patents
Delta3-cephalosporin compounds and process for their preparation from delta2-cephalosporinInfo
- Publication number
- IL40447A IL40447A IL40447A IL4044769A IL40447A IL 40447 A IL40447 A IL 40447A IL 40447 A IL40447 A IL 40447A IL 4044769 A IL4044769 A IL 4044769A IL 40447 A IL40447 A IL 40447A
- Authority
- IL
- Israel
- Prior art keywords
- compound
- alkyl
- hydrogen
- amino
- tert
- Prior art date
Links
- 229940124587 cephalosporin Drugs 0.000 title claims 3
- 150000001875 compounds Chemical class 0.000 claims 26
- 229910052739 hydrogen Inorganic materials 0.000 claims 16
- 239000001257 hydrogen Substances 0.000 claims 16
- -1 nitro, hydroxy Chemical group 0.000 claims 14
- 150000002431 hydrogen Chemical class 0.000 claims 10
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 9
- 229910052717 sulfur Chemical group 0.000 claims 9
- 239000011593 sulfur Chemical group 0.000 claims 9
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 7
- 229910052760 oxygen Inorganic materials 0.000 claims 7
- 239000001301 oxygen Substances 0.000 claims 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 4
- 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 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 4
- 229910052794 bromium Inorganic materials 0.000 claims 4
- 239000000460 chlorine Substances 0.000 claims 4
- 229910052801 chlorine Inorganic materials 0.000 claims 4
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 4
- 239000011734 sodium Substances 0.000 claims 4
- 229910052708 sodium Inorganic materials 0.000 claims 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 229910052731 fluorine Inorganic materials 0.000 claims 3
- 239000011737 fluorine Substances 0.000 claims 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- 125000005605 benzo group Chemical group 0.000 claims 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 150000001768 cations Chemical class 0.000 claims 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 2
- 229940126214 compound 3 Drugs 0.000 claims 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 239000000126 substance Chemical group 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- 239000004215 Carbon black (E152) Substances 0.000 claims 1
- 241001024304 Mino Species 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 150000001412 amines Chemical group 0.000 claims 1
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000002541 furyl group Chemical group 0.000 claims 1
- 229930195733 hydrocarbon Natural products 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000006502 nitrobenzyl group Chemical group 0.000 claims 1
- 239000007800 oxidant agent Substances 0.000 claims 1
- 150000003462 sulfoxides Chemical class 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims 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
- C07D501/02—Preparation
- C07D501/04—Preparation from compounds already containing the ring or condensed ring systems, e.g. by dehydrogenation of the ring, by introduction, elimination or modification of substituents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/54—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame
- A61K31/542—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame ortho- or peri-condensed with heterocyclic ring systems
- A61K31/545—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, cefaclor, or cephalexine
-
- 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
-
- 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
-
- 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
- C07D501/60—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 3 and 4
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Cephalosporin Compounds (AREA)
Claims (6)
1. WHAT WE CLAIM IS: A process for producing a compound of the formula S R-NH-CH-CH CH, 0=C N C-CH„-R' COOR" wherein R is hydrogen; .mino where X is amino, butoxycarbony nydrpxy, carboxyl, or to Cj-alkanoyloxy; where X is oxygen or sulfur or a chemical bond, y is an integer of from 0 to 2, and z is an integer of from 1 to 2 , and Q in each of the above phenyl rings is hydrogen, C^ to C^ ^^y^ Cj to Cj- alkoxy, nitro, hydroxy, chloro, bromo, fluoro, trifiuoro-methyl, carfcoxymethyl (KOOC-CH2-) or carbamoylnethyl (H2NIfi:(0)CH2-) , —62— 40447/4 Z-C CH II li Z-C C-CH-CO- ; where Y is sulfur, and each Z separately denotes hydrogen, or taken together with the carbons to which they are bonded, complete a benzo-ring, wherein e to to Cj-alkanoyl where X is oxygen or sulfur C2 to -haloalkanoyl where halogen is luorine, chlorine, or bromine, or R' is cyano or -0Y where Y is to C1Q-alkyl, C3 to C10-alkenyf, C3 to C10-alfcynyl , to C3-alkyl-X-C2 to C&-alky1 where X is oxygen or sulfur C2 to C4-alkanoyloxy-C2 to C^-alkyl, (furyl)-^ to C3-alkyl, 3' -tetrahydrofuryl 40447/3 tetrahydrofuryl-Cj to Cj-alkyl phenyl or benzyl, which are substituted on ring carbon atoms thereof with Cj to C^-alkyl, to Cg-alkoxy, Cj to Cj-alkoxycarbonyl, fluorine, chlorine, bromine, nitro, cyano or trifluoromethyl ; and R" is hydrogen a zwitterionic charge, a salt with pharmaceutically acceptable cation, C4 to C6-tert-alkyl, benzyl , methoxybenzyl or nitrobenzyl 2 which comprises reacting the corresponding ^ -compounds : C00R" where R' arid R" are defined as above and R'" is phenoxyacetyl , thio-pheneacetyl or phenylacetyl, with an oxidizing agent to produce the 3 3 corresponding ^ sulfoxide and then reducing to produce said -cephalosporin ester compound and if desired optionally cleaVing the R'" group from the seven position to provide the R group as defined above, and when desired preparing the salts.
2. A process according to claim 1, wherein the compound produced is that in which R is hydrogen, R' is cyano, " is a to Cg-tert-alkyl , -or a to C-^-aromatic hydrocarbon sulfonic acid salt of such a compound. 40447/3
3. A process according to claim 1 or 2 wherein the compound 3 produced is tert-batty1 7-amino-3-cyanomethyl-^ -cephem-4-carboxylate or a p-toluenesulfonate salt thereof.
4. A process according to claim 1 wherein the compound produced is that in which R is hydrogen, R' is -0Y, Y is to C1Q-alkyl, and R" is C4 to Cg-tert-alkyl or a to C-^-aromatic hydrocarbon sulfonic acid salt of such a compound.
5. A process according to claim 1 or 4 wherein the compound produced is tert-butyl 7-amino-3-methoxy-methyl-^-cephem-4-carboxylic acid, or a p-toluenesulfonate salt thereof.
6. A process according to claim 1, wherein the compound produced is that in which R is butoxycarbonylamino, hydroxy where X is amino, protected amino, to C^-alltoxy, -C00H, or to Cg-iilkanoyloxy, and Q is hydrogen, R' is -0Y, Y is to C^-allcyl, and R" is hydrogen, or a sodium or potassium salt of such a compound. 7* A process according to claim 1 or 6, wherein the compound 3 produced is 7-(D-21 amino-2 'phenyl-acetamido) -5-methoxymethyl ^ -cephem-4-carboxylic acid* 8i A process according to claim 1 or 6, wherein the compound produced is 7^ [o-^-hydroxy-^-phenyl-acetaiiiido -3-methoxymethyl-j$-cephem-4-carboxylic acid or the sodium or potassium salt of such a compound* -65 - 40447/3 9. A compound of the formula S ^ \ R-NH-CH»CH CH_ I I i 2 0=C-N C-CH-- 2 c I I C00R'; wherein R is hydrogen; amine where X is amino., butoxycarbonyy hydroxy, carboxyl, or to C -alkanoyloxy; where X is oxygen or sulfur or a chemical bond, y is an integer of from 0 to 2, and z is an integer of from 1 to 2; and Q in each of the above phenyl rings is hydrogen, Cj to alkyl Cj to Cj-alkoxy, nitro, hydroxy, chloro, brorao, fluoro, trifluoro-methyi, carboxymethyi (H00C-CH2-) or carbamoylmethyl (H_N|C(0)CH7-) , where Y is sulfur, and each Z taken together with the carbons to which they are bonded, complete benzo-ring, C-CH-CO- il l2 N N R ■ 0 1 2 wherein each of R and R is hydrogen., or methyl; 2-sydnone-3-C^ to C^-alkanoyl-, Cj to CjQ-alkanoyl, to C^-alkenoyl, Cj to C7~alk l-X-Cj to Cg-alkanoyl where X is oxygen or sulfur, Cj to C7~alkenyl-X-Cj to C^-alkanoyl where X is oxygen or sulfur, to CjQ-haloakanoyl where halogen is fluorine, chlorine, or bromine, or C2 to CjQ-cyanoalkanoyl ; R» is cyano or -0Y where Y is Cj to C10-alkyl Cj to C^g-alkenyl C2 to CjQ-haloalkyl, C.to C^-alkyl-X-C^ to C^-alkyl where X is oxygen or sulfur, C2 to C^-alkanoyloxy-C2 to C,-alkyl, C2 to to (_6-alkyl (furyl)-C. to C,-alkyl, 1 3· tetrahydrofuryl tetrahydrofuryl-Cj to Cg-alkyl phenyl or benzyl, which a o substituted on ring carbon atoms thereof with to C^-alkyl, to C^-alkoxy, to Cj-alkoxycarbonyl, fluorine, chlorine, bromine, nitro, cyano or trifluoromethyl ; 40447/3 and R" is hydrogen a zwitterionic charge, a salt with pharmaceutically acceptable cation, C4 to Cg-tert-alkyl , benzyl, methoxybenzyl or nitx-obenzyl . 10. The compound of claim 9, wherein R is hydrogen, R' is cyano R" is a C4 to C^-tert-alkyl , or a to C^-aromatic hydrocarbon sulfonic acid salt of such a compound. 11. The compound of claim 9 or 10, wherein the compound is tert- 3 butyl 7-amino-3-cyanomethyl-^ -cephem-4-carboxylate or a p-toluenesul-fonate salt thereof. 12. The compound of claim 9 wherein R is hydrogen, R* is -0Y, Y is C to C1()-alkyl. and R" is to Cg-tert-alkyl or a C& to C12~ arorofctic hydrocarbon sulfonic acid salt of such a compound. 13. The compound of claim 9 or 12, wherein the compound is tert- 3 butyl 7-amino-3-methoxymethyl-^ -cephem-4-carboxylic acid, or a p-toluenesulfonate salt thereof. 14. The compound of claim 9, wherein R is X butoxycarbonylamino, hydroxy where X is amino, a protoetod amino, C^, to C^-alkoxy, -CCOH, or to Cj-alkanoyloxy, and Q is hydrogen, R' is -0Y, Y is to CjQ-alkyl, and R" is hydrogen, or a sodium or potassium salt of such a compound. 40447/3 15. The compound of claim 9 or 14, wherein the compound is 7-(D-2 ' -amino-2 ' -phenylacetamido) -3-methoxymeth l ^-cephem-4-carboxylic acid. 16. The compound of claim 9 or 14 , wherein the compound is 7- |)-¾^-hydroxy-_Y-phenylacetamido~J -3-methoxymethyl-^-cephem-4-carboxylic acid or the sodium or potassium salt of such a compound. S.HOROWITZ fT CO. AGENTS FOR APPLICANTS
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US70352368A | 1968-02-07 | 1968-02-07 | |
| US79084269A | 1969-01-13 | 1969-01-13 | |
| US79088669A | 1969-01-13 | 1969-01-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| IL40447A true IL40447A (en) | 1976-02-29 |
Family
ID=27418758
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL40447A IL40447A (en) | 1968-02-07 | 1969-02-06 | Delta3-cephalosporin compounds and process for their preparation from delta2-cephalosporin |
| IL41553A IL41553A (en) | 1968-02-07 | 1969-02-06 | 3-bromomethyl-delta2-cephalosporin compounds and process for preparing the same |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL41553A IL41553A (en) | 1968-02-07 | 1969-02-06 | 3-bromomethyl-delta2-cephalosporin compounds and process for preparing the same |
Country Status (11)
| Country | Link |
|---|---|
| JP (3) | JPS524558B1 (en) |
| BE (1) | BE728053A (en) |
| CH (1) | CH534694A (en) |
| DK (1) | DK140726B (en) |
| FI (1) | FI56535C (en) |
| FR (3) | FR2001491B1 (en) |
| GB (2) | GB1265333A (en) |
| IL (2) | IL40447A (en) |
| LU (1) | LU57932A1 (en) |
| NL (1) | NL173407C (en) |
| SE (3) | SE384511B (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2132883A1 (en) * | 1970-07-08 | 1972-01-13 | Ciba Geigy Ag | Cephem compounds |
| JPS53164082U (en) * | 1977-05-31 | 1978-12-22 | ||
| JPS5899787U (en) * | 1981-12-28 | 1983-07-07 | 奥野電器株式会社 | lamp socket |
| EP0300546B1 (en) * | 1987-07-10 | 1995-08-09 | Gist-Brocades N.V. | Process for the preparation of cephem compounds and cephalosporin derivatives |
-
1969
- 1969-02-04 FI FI326/69A patent/FI56535C/en active
- 1969-02-05 SE SE6901500A patent/SE384511B/en unknown
- 1969-02-06 IL IL40447A patent/IL40447A/en unknown
- 1969-02-06 LU LU57932D patent/LU57932A1/xx unknown
- 1969-02-06 IL IL41553A patent/IL41553A/en unknown
- 1969-02-06 DK DK63069AA patent/DK140726B/en not_active IP Right Cessation
- 1969-02-07 GB GB1265333D patent/GB1265333A/en not_active Expired
- 1969-02-07 CH CH190469A patent/CH534694A/en not_active IP Right Cessation
- 1969-02-07 GB GB1265332D patent/GB1265332A/en not_active Expired
- 1969-02-07 FR FR696902897A patent/FR2001491B1/fr not_active Expired
- 1969-02-07 NL NLAANVRAGE6902013,A patent/NL173407C/en not_active IP Right Cessation
- 1969-02-07 BE BE728053D patent/BE728053A/xx not_active IP Right Cessation
- 1969-02-07 JP JP44009211A patent/JPS524558B1/ja active Pending
-
1971
- 1971-03-03 FR FR7107344A patent/FR2095486A5/fr not_active Expired
- 1971-03-03 FR FR7107345A patent/FR2085656B1/fr not_active Expired
- 1971-08-13 JP JP46061595A patent/JPS524559B1/ja active Pending
- 1971-08-13 JP JP46061594A patent/JPS4924076B1/ja active Pending
-
1972
- 1972-01-14 SE SE7200411A patent/SE407064B/en unknown
-
1975
- 1975-11-14 SE SE7512818A patent/SE418616B/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| FR2001491B1 (en) | 1973-07-13 |
| JPS524559B1 (en) | 1977-02-04 |
| BE728053A (en) | 1969-08-07 |
| GB1265332A (en) | 1972-03-01 |
| LU57932A1 (en) | 1969-09-17 |
| FR2001491A1 (en) | 1969-09-26 |
| SE384511B (en) | 1976-05-10 |
| JPS4924076B1 (en) | 1974-06-20 |
| FR2085656A1 (en) | 1971-12-31 |
| GB1265333A (en) | 1972-03-01 |
| DK140726B (en) | 1979-11-05 |
| IL41553A (en) | 1976-02-29 |
| NL6902013A (en) | 1969-08-11 |
| DK140726C (en) | 1980-03-31 |
| FR2085656B1 (en) | 1974-08-23 |
| NL173407C (en) | 1984-01-16 |
| FR2095486A5 (en) | 1972-02-11 |
| SE407064B (en) | 1979-03-12 |
| NL173407B (en) | 1983-08-16 |
| SE7512818L (en) | 1975-11-14 |
| FI56535C (en) | 1980-02-11 |
| JPS524558B1 (en) | 1977-02-04 |
| CH534694A (en) | 1973-03-15 |
| SE418616B (en) | 1981-06-15 |
| FI56535B (en) | 1979-10-31 |
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