IE33077L - Epoxypropylphosphonic acid derivatives - Google Patents
Epoxypropylphosphonic acid derivativesInfo
- Publication number
- IE33077L IE33077L IE681254A IE125468A IE33077L IE 33077 L IE33077 L IE 33077L IE 681254 A IE681254 A IE 681254A IE 125468 A IE125468 A IE 125468A IE 33077 L IE33077 L IE 33077L
- Authority
- IE
- Ireland
- Prior art keywords
- compounds
- cis
- salts
- agents
- oxygen
- Prior art date
Links
- 239000002253 acid Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 18
- 229910052760 oxygen Inorganic materials 0.000 abstract 10
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 8
- 239000007800 oxidant agent Substances 0.000 abstract 8
- 239000001301 oxygen Substances 0.000 abstract 8
- 150000003839 salts Chemical class 0.000 abstract 8
- -1 1,2 - Epoxypropyl Chemical group 0.000 abstract 6
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 abstract 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 abstract 4
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 abstract 4
- 238000006243 chemical reaction Methods 0.000 abstract 4
- 239000003795 chemical substances by application Substances 0.000 abstract 4
- 229910052736 halogen Inorganic materials 0.000 abstract 4
- 150000002367 halogens Chemical class 0.000 abstract 4
- 125000001183 hydrocarbyl group Chemical group 0.000 abstract 4
- 239000000203 mixture Substances 0.000 abstract 4
- 150000004967 organic peroxy acids Chemical class 0.000 abstract 4
- XYPISWUKQGWYGX-UHFFFAOYSA-N 2,2,2-trifluoroethaneperoxoic acid Chemical compound OOC(=O)C(F)(F)F XYPISWUKQGWYGX-UHFFFAOYSA-N 0.000 abstract 2
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 abstract 2
- 239000004215 Carbon black (E152) Substances 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 abstract 2
- BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical class NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 abstract 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 2
- 239000005864 Sulphur Substances 0.000 abstract 2
- 239000003513 alkali Substances 0.000 abstract 2
- 150000001342 alkaline earth metals Chemical class 0.000 abstract 2
- 150000001412 amines Chemical class 0.000 abstract 2
- 125000003277 amino group Chemical group 0.000 abstract 2
- 230000000844 anti-bacterial effect Effects 0.000 abstract 2
- 125000000732 arylene group Chemical group 0.000 abstract 2
- 239000011230 binding agent Substances 0.000 abstract 2
- 229910052791 calcium Inorganic materials 0.000 abstract 2
- 239000002775 capsule Substances 0.000 abstract 2
- ONANWDUDFJIIGP-UHFFFAOYSA-N carbamoyl carbamoperoxoate Chemical compound NC(=O)OOC(N)=O ONANWDUDFJIIGP-UHFFFAOYSA-N 0.000 abstract 2
- 239000011248 coating agent Substances 0.000 abstract 2
- 125000004122 cyclic group Chemical group 0.000 abstract 2
- 239000003085 diluting agent Substances 0.000 abstract 2
- 229940042400 direct acting antivirals phosphonic acid derivative Drugs 0.000 abstract 2
- 238000006735 epoxidation reaction Methods 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- 239000000796 flavoring agent Substances 0.000 abstract 2
- 235000013355 food flavoring agent Nutrition 0.000 abstract 2
- 238000009472 formulation Methods 0.000 abstract 2
- 239000003979 granulating agent Substances 0.000 abstract 2
- 125000000623 heterocyclic group Chemical group 0.000 abstract 2
- 229930195733 hydrocarbon Natural products 0.000 abstract 2
- 150000002430 hydrocarbons Chemical class 0.000 abstract 2
- 150000002432 hydroperoxides Chemical class 0.000 abstract 2
- JGJLWPGRMCADHB-UHFFFAOYSA-N hypobromite Inorganic materials Br[O-] JGJLWPGRMCADHB-UHFFFAOYSA-N 0.000 abstract 2
- 238000011065 in-situ storage Methods 0.000 abstract 2
- 238000002347 injection Methods 0.000 abstract 2
- 239000007924 injection Substances 0.000 abstract 2
- 150000004966 inorganic peroxy acids Chemical class 0.000 abstract 2
- 239000006193 liquid solution Substances 0.000 abstract 2
- 239000006194 liquid suspension Substances 0.000 abstract 2
- 229910052749 magnesium Inorganic materials 0.000 abstract 2
- 150000002825 nitriles Chemical class 0.000 abstract 2
- 125000000864 peroxy group Chemical group O(O*)* 0.000 abstract 2
- 125000004437 phosphorous atom Chemical group 0.000 abstract 2
- 229910052698 phosphorus Inorganic materials 0.000 abstract 2
- 239000003755 preservative agent Substances 0.000 abstract 2
- 239000000376 reactant Substances 0.000 abstract 2
- 229910052708 sodium Inorganic materials 0.000 abstract 2
- 239000007858 starting material Substances 0.000 abstract 2
- 229910052717 sulfur Inorganic materials 0.000 abstract 2
- 150000003573 thiols Chemical class 0.000 abstract 2
- 229910052727 yttrium Inorganic materials 0.000 abstract 2
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
- C07F9/6571—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 oxygen atoms as the only ring hetero atoms
- C07F9/657163—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 oxygen atoms as the only ring hetero atoms the ring phosphorus atom being bound to at least one carbon atom
- C07F9/657181—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 oxygen atoms as the only ring hetero atoms the ring phosphorus atom being bound to at least one carbon atom the ring phosphorus atom and, at least, one ring oxygen atom being part of a (thio)phosphonic acid derivative
-
- 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
- C07F9/655—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms
- C07F9/65502—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms the oxygen atom being part of a three-membered ring
- C07F9/65505—Phosphonic acids containing oxirane groups; esters thereof
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
1,236,956. (cis 1,2 - Epoxypropyl) - phosphonic acid derivatives. MERCK & CO. Inc. 24 Oct., 1968 [15 May, 1968], No. 50634/68. Heading C2C. The invention comprises a mixture of the (+) and (-) enantiomers of (cis 1,2-epoxypropyl)-phosphonic acid compounds of the formula in which X is O or S, Y is -OR, -SR, -NR 1 R 2 or halogen and Z is -OR, -SR, -NR 1 R 2 or halogen, with the proviso that at least one of Y and Z is other than -OR when X is oxygen, R is H or a substituted or unsubstituted hydrocarbyl or heterocyclic radical and each of R 1 and R 2 is H, a substituted or unsubstituted hydrocarbyl or heterocyclic radical or an acyl radical or NR 1 R 2 represents a heterocyclic amino group, also the cyclic derivatives of such compounds in which Y and Z are joined together by a divalent radical, e.g. polymethylene or arylene, and salts of such compounds in which at least one of Y and Z is -OH or -SH. The invention also comprises ( ) cis compounds of the formula or or in which X and Z are as defined above, A is -O-, -S- or -NR-, R 1 and R 2 when present in Z being a substituted or unsubstituted hydrocarbon or heterocyclic radical or an acyl radical, R 3 is H, an alkali or alkaline earth metal or C 1 -C 6 alkyl, with the proviso that at least one of X, Z and A is other than oxygen or an oxygen-containing radical. The compounds (I) may be obtained by the epoxidation of a compound of the formula with an oxidizing agent and compounds of Formul (II), (III) and (IV) may be prepared by treating a compound of the formula or or with an oxidizing agent. Several suitable oxidizing agents are specified, the preferred agents being peroxy compounds such as H 2 O 2 , an inorganic or organic per acid (including optically active organic per acids), an organic hydroperoxide or peroxyimidic acid which may be formed in situ from H 2 O 2 and a nitrile. The compounds may also be obtained by reacting the corresponding cis-propenyl phosphonous acid derivatives with an oxidizing agent as above so as to convert the phosphorus atom from P<SP>III</SP> to P<SP>v</SP> and to epoxidize the olefinic double bond in the one reaction. The products when they are other than salts may be converted to salts, e.g. the Na, Ca, Mg, piperazine, ethylenediamine, benzylamine or phenethylamine salts. The cis-propenyl phosphonic compounds used as starting materials may be obtained from the cis-propenyl phosphonic (or thiophosphonic)-dichloride by reacting with an alcohol, thiol or amine, the reaction being carried out with more than one such reactant and in more than one stage as appropriate and when X in the products is sulphur the latter may be replaced by oxygen by treatment with peroxy-trifluoroacetic acid or with bromine water. The ( )(cis - 1,2 - epoxypropyl)-phosphonic acid and its salts and labile esters have antibacterial properties and may be administered orally, e.g. as capsules or tablets or in an orally administratable liquid solution or suspension. The formulations may be prepared from diluents, granulating agents, preservatives, binders, flavouring agents and coating agents. The agents may also be administered parenterally by injection in a sterile vehicle.
1,236,956. (cis 1,2 - Epoxypropyl) - phosphonic acid derivatives. MERCK & CO. Inc. 24 Oct., 1968 [15 May, 1968], No. 50634/68. Heading C2C. The invention comprises a mixture of the (+) and (-) enantiomers of (cis 1,2-epoxypropyl)-phosphonic acid compounds of the formula in which X is O or S, Y is -OR, -SR, -NR 1 R 2 or halogen and Z is -OR, -SR, -NR 1 R 2 or halogen, with the proviso that at least one of Y and Z is other than -OR when X is oxygen, R is H or a substituted or unsubstituted hydrocarbyl or heterocyclic radical and each of R 1 and R 2 is H, a substituted or unsubstituted hydrocarbyl or heterocyclic radical or an acyl radical or NR 1 R 2 represents a heterocyclic amino group, also the cyclic derivatives of such compounds in which Y and Z are joined together by a divalent radical, e.g. polymethylene or arylene, and salts of such compounds in which at least one of Y and Z is -OH or -SH. The invention also comprises () cis compounds of the formula or or in which X and Z are as defined above, A is -O-, -S- or -NR-, R 1 and R 2 when present in Z being a substituted or unsubstituted hydrocarbon or heterocyclic radical or an acyl radical, R 3 is H, an alkali or alkaline earth metal or C 1 -C 6 alkyl, with the proviso that at least one of X, Z and A is other than oxygen or an oxygen-containing radical. The compounds (I) may be obtained by the epoxidation of a compound of the formula with an oxidizing agent and compounds of Formulµ (II), (III) and (IV) may be prepared by treating a compound of the formula or or with an oxidizing agent. Several suitable oxidizing agents are specified, the preferred agents being peroxy compounds such as H 2 O 2 , an inorganic or organic per acid (including optically active organic per acids), an organic hydroperoxide or peroxyimidic acid which may be formed in situ from H 2 O 2 and a nitrile. The compounds may also be obtained by reacting the corresponding cis-propenyl phosphonous acid derivatives with an oxidizing agent as above so as to convert the phosphorus atom from P<SP>III</SP> to P<SP>v</SP> and to epoxidize the olefinic double bond in the one reaction. The products when they are other than salts may be converted to salts, e.g. the Na, Ca, Mg, piperazine, ethylenediamine, benzylamine or phenethylamine salts. The cis-propenyl phosphonic compounds used as starting materials may be obtained from the cis-propenyl phosphonic (or thiophosphonic)-dichloride by reacting with an alcohol, thiol or amine, the reaction being carried out with more than one such reactant and in more than one stage as appropriate and when X in the products is sulphur the latter may be replaced by oxygen by treatment with peroxy-trifluoroacetic acid or with bromine water. The ()(cis - 1,2 - epoxypropyl)-phosphonic acid and its salts and labile esters have antibacterial properties and may be administered orally, e.g. as capsules or tablets or in an orally administratable liquid solution or suspension. The formulations may be prepared from diluents, granulating agents, preservatives, binders, flavouring agents and coating agents. The agents may also be administered parenterally by injection in a sterile vehicle.
[GB1236956A]
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US72942968A | 1968-05-15 | 1968-05-15 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE33077L true IE33077L (en) | 1969-11-15 |
| IE33077B1 IE33077B1 (en) | 1974-03-20 |
Family
ID=24930977
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE1254/68A IE33077B1 (en) | 1968-05-15 | 1968-10-21 | Epoxypropylphoshonic and thiophosphonic acid derivatives |
Country Status (17)
| Country | Link |
|---|---|
| AT (1) | AT299245B (en) |
| BE (1) | BE723079A (en) |
| BR (1) | BR6803537D0 (en) |
| CH (1) | CH515937A (en) |
| DE (1) | DE1805675A1 (en) |
| ES (1) | ES359535A1 (en) |
| FR (1) | FR2008618A1 (en) |
| GB (1) | GB1236956A (en) |
| HU (1) | HU162829B (en) |
| IE (1) | IE33077B1 (en) |
| IL (1) | IL30915A0 (en) |
| LU (1) | LU57187A1 (en) |
| MT (1) | MTP584B (en) |
| NL (1) | NL6814981A (en) |
| PL (1) | PL71417B1 (en) |
| SE (1) | SE367205B (en) |
| ZM (1) | ZM14068A1 (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN117964661B (en) * | 2024-04-01 | 2024-06-07 | 深圳创元生物医药科技有限公司 | Preparation method of fosfomycin genotoxic impurity C |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2770610A (en) * | 1952-10-30 | 1956-11-13 | Monsanto Chemicals | Esters of epoxidized phosphonic acids and halogenated organic materials stabilized therewith |
-
1968
- 1968-10-18 NL NL6814981A patent/NL6814981A/xx unknown
- 1968-10-21 IE IE1254/68A patent/IE33077B1/en unknown
- 1968-10-21 IL IL30915A patent/IL30915A0/en unknown
- 1968-10-22 CH CH1578768A patent/CH515937A/en not_active IP Right Cessation
- 1968-10-23 HU HUME997A patent/HU162829B/hu unknown
- 1968-10-24 PL PL1968129715A patent/PL71417B1/pl unknown
- 1968-10-24 GB GB50634/68A patent/GB1236956A/en not_active Expired
- 1968-10-25 ES ES359535A patent/ES359535A1/en not_active Expired
- 1968-10-28 DE DE19681805675 patent/DE1805675A1/en active Pending
- 1968-10-29 BE BE723079D patent/BE723079A/xx unknown
- 1968-10-29 BR BR203537/68A patent/BR6803537D0/en unknown
- 1968-10-29 LU LU57187D patent/LU57187A1/xx unknown
- 1968-10-29 SE SE14614/68A patent/SE367205B/xx unknown
- 1968-10-30 AT AT1055568A patent/AT299245B/en not_active IP Right Cessation
- 1968-10-30 ZM ZM140/68A patent/ZM14068A1/en unknown
- 1968-11-11 MT MT584A patent/MTP584B/en unknown
-
1969
- 1969-05-16 FR FR6915920A patent/FR2008618A1/fr not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| LU57187A1 (en) | 1969-05-16 |
| IL30915A0 (en) | 1968-12-26 |
| MTP584B (en) | 1970-01-21 |
| IE33077B1 (en) | 1974-03-20 |
| SE367205B (en) | 1974-05-20 |
| FR2008618A1 (en) | 1970-01-23 |
| GB1236956A (en) | 1971-06-23 |
| NL6814981A (en) | 1969-11-18 |
| CH515937A (en) | 1971-11-30 |
| DE1805675A1 (en) | 1969-12-11 |
| BR6803537D0 (en) | 1973-02-22 |
| PL71417B1 (en) | 1974-06-29 |
| AT299245B (en) | 1972-06-12 |
| ES359535A1 (en) | 1970-08-16 |
| BE723079A (en) | 1969-04-29 |
| ZM14068A1 (en) | 1970-06-18 |
| HU162829B (en) | 1973-04-28 |
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