IE37510B1 - 7-azido-cephalosporin compounds and their preparation - Google Patents
7-azido-cephalosporin compounds and their preparationInfo
- Publication number
- IE37510B1 IE37510B1 IE562/73A IE56273A IE37510B1 IE 37510 B1 IE37510 B1 IE 37510B1 IE 562/73 A IE562/73 A IE 562/73A IE 56273 A IE56273 A IE 56273A IE 37510 B1 IE37510 B1 IE 37510B1
- Authority
- IE
- Ireland
- Prior art keywords
- azido
- acid
- reacted
- reaction
- ester
- Prior art date
Links
- 229940124587 cephalosporin Drugs 0.000 title abstract 3
- 238000002360 preparation method Methods 0.000 title abstract 2
- -1 carbamoyloxy Chemical group 0.000 abstract 7
- 238000006243 chemical reaction Methods 0.000 abstract 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical class CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 4
- 150000003839 salts Chemical class 0.000 abstract 4
- 239000002253 acid Substances 0.000 abstract 3
- 150000001412 amines Chemical class 0.000 abstract 3
- 229910052736 halogen Inorganic materials 0.000 abstract 3
- 150000002367 halogens Chemical class 0.000 abstract 3
- 239000000543 intermediate Substances 0.000 abstract 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 abstract 2
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 abstract 2
- 239000002585 base Substances 0.000 abstract 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 abstract 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 2
- RPAJSBKBKSSMLJ-DFWYDOINSA-N (2s)-2-aminopentanedioic acid;hydrochloride Chemical class Cl.OC(=O)[C@@H](N)CCC(O)=O RPAJSBKBKSSMLJ-DFWYDOINSA-N 0.000 abstract 1
- HORQAOAYAYGIBM-UHFFFAOYSA-N 2,4-dinitrophenylhydrazine Chemical compound NNC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O HORQAOAYAYGIBM-UHFFFAOYSA-N 0.000 abstract 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 abstract 1
- IOVQBHMSPTUQAQ-UHFFFAOYSA-N 2-azido-2-methoxyacetic acid Chemical compound COC(C(O)=O)N=[N+]=[N-] IOVQBHMSPTUQAQ-UHFFFAOYSA-N 0.000 abstract 1
- HWPXTDXPHUUFID-UHFFFAOYSA-N 2-azido-2-methoxyacetyl chloride Chemical compound COC(C(Cl)=O)N=[N+]=[N-] HWPXTDXPHUUFID-UHFFFAOYSA-N 0.000 abstract 1
- PPXUUPXQWDQNGO-UHFFFAOYSA-N 2-azidoacetic acid Chemical compound OC(=O)CN=[N+]=[N-] PPXUUPXQWDQNGO-UHFFFAOYSA-N 0.000 abstract 1
- AGIJRRREJXSQJR-UHFFFAOYSA-N 2h-thiazine Chemical compound N1SC=CC=C1 AGIJRRREJXSQJR-UHFFFAOYSA-N 0.000 abstract 1
- 229930186147 Cephalosporin Natural products 0.000 abstract 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 abstract 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 abstract 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 abstract 1
- 239000002262 Schiff base Substances 0.000 abstract 1
- 150000004753 Schiff bases Chemical class 0.000 abstract 1
- 125000004423 acyloxy group Chemical group 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000005083 alkoxyalkoxy group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000002102 aryl alkyloxo group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 125000004104 aryloxy group Chemical group 0.000 abstract 1
- HUMNYLRZRPPJDN-KWCOIAHCSA-N benzaldehyde Chemical group O=[11CH]C1=CC=CC=C1 HUMNYLRZRPPJDN-KWCOIAHCSA-N 0.000 abstract 1
- 230000000903 blocking effect Effects 0.000 abstract 1
- 239000003153 chemical reaction reagent Substances 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 150000002466 imines Chemical class 0.000 abstract 1
- BRMYZIKAHFEUFJ-UHFFFAOYSA-L mercury diacetate Chemical compound CC(=O)O[Hg]OC(C)=O BRMYZIKAHFEUFJ-UHFFFAOYSA-L 0.000 abstract 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- JNKVFSFFZPJLMW-UHFFFAOYSA-N methyl 2-azido-2-methoxyacetate Chemical compound [N-]=[N+]=NC(OC)C(=O)OC JNKVFSFFZPJLMW-UHFFFAOYSA-N 0.000 abstract 1
- DCOWHZYIFORKFC-UHFFFAOYSA-N methyl 2-chloro-2-methoxyacetate Chemical compound COC(Cl)C(=O)OC DCOWHZYIFORKFC-UHFFFAOYSA-N 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- KTKAAPWVXFAGIT-UHFFFAOYSA-N methylsulfonyl 2-azidoacetate Chemical compound CS(=O)(=O)OC(=O)CN=[N+]=[N-] KTKAAPWVXFAGIT-UHFFFAOYSA-N 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 238000006386 neutralization reaction Methods 0.000 abstract 1
- 150000002900 organolithium compounds Chemical class 0.000 abstract 1
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 abstract 1
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 abstract 1
- ULUATRKSGFEGOE-UHFFFAOYSA-N prop-1-en-2-yl 2-azidoacetate Chemical compound CC(=C)OC(=O)CN=[N+]=[N-] ULUATRKSGFEGOE-UHFFFAOYSA-N 0.000 abstract 1
- MWWATHDPGQKSAR-UHFFFAOYSA-N propyne Chemical group CC#C MWWATHDPGQKSAR-UHFFFAOYSA-N 0.000 abstract 1
- QRUBYZBWAOOHSV-UHFFFAOYSA-M silver trifluoromethanesulfonate Chemical compound [Ag+].[O-]S(=O)(=O)C(F)(F)F QRUBYZBWAOOHSV-UHFFFAOYSA-M 0.000 abstract 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 abstract 1
- QTXBEQGZSJCCAU-UHFFFAOYSA-N trifluoromethylsulfonyl 2-azidoacetate Chemical compound FC(F)(F)S(=O)(=O)OC(=O)CN=[N+]=[N-] QTXBEQGZSJCCAU-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
- C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D257/04—Five-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C265/00—Derivatives of isocyanic acid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/09—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid esters or lactones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/58—Preparation of carboxylic acid halides
- C07C51/60—Preparation of carboxylic acid halides by conversion of carboxylic acids or their anhydrides or esters, lactones, salts into halides with the same carboxylic acid part
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
- C07D285/125—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
-
- 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
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4006—Esters of acyclic acids which can have further substituents on alkyl
-
- 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
- C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
- C07F9/568—Four-membered rings
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)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Cephalosporin Compounds (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
1424373 dl - 7 - Azido - cephalosporin compounds; phosphonate intermediates MERCK & CO Inc 10 April 1973 [14 April 1972 30 June 1972 (2) 10 Oct 1972 5 March 1973] 17050/73 Headings C2C and C2P Novel dl-7-azido-cephalosporin compounds of the Formula (V) in which R is alkyl or aryl, R 1 is a blocking group, R<SP>1</SP> is H, halogen, carbamoyloxy, which may be N-substituted or N,N-disubstituted, alkoxyalkoxy, alkoxy, aryloxy, aralkyloxy, heterocyclic-thio or acyloxy, and B is H, the azido being in α-position or B is -CH 3 or -OCH 3 , the azido then being in #-position, may be obtained by the processes shown in the flowsheet (A) wherein (I) is reacted with a thioformylating agent (e.g. a thionoformate ester) to form (II), which is reacted with a substituted acetone R<SP>1</SP>CH 2 COCH 2 X, where X is halogen or a sulphonate ester, to form (III), the latter is converted to thiazine (IV), or alternatively (IV) is formed directly by reaction of II and the substituted acetone, and finally (IV) is reacted with an azido acetyl reagent where X<SP>1</SP> is halogen, p-toluenesulphonyloxy, -OSO 2 CF 3 or -OSO 2 CH 3 , in the presence of a base. Alternatively, the desired 7-azido compound (V) is obtained by reacting a mixture of III and IV or IV or III per se with the azidoacetyl compound. An intermediate, 1,3,5-tribenzyl-sym-hexahydrotriazine (XXIII) is obtained by reacting benzylamine with formaldehyde, and the α- aminophosphonoacetate ester (I) is obtained as in the following flowsheet (B) XXIII is reacted with a disubstituted phosphite to yield XXIV, isolated as an acid salt, the latter is reduced in the presence of Pd/C forming the salt of XXV. The salt is connected to the amine XXVI by reaction with NH 3 . The amine on reaction with benzaldehyde forms a Schiff base XXVII, which on reaction with a strong base, e.g. an organolithium compound and then a haloformate ester forms imine XXVIII. Treatment of this imine with 2,4- dinitrophenyl hydrazine in the presence of p-toluenesulphonic acid monohdyrate or with p-toluenesulphonic acid hydrate in ether followed by neutralization of the amine acid salt yields the compound I. Other intermediate preparations described are: reaction of methyl 2-chloro-2-methoxyacetate and NaN 3 to give methyl 2-azido-2- methoxyacetate, hydrolysed to 2-azido-2- methoxyacetic acid and reaction with thionyl chloride to 2-azido-2-methoxyacetyl chloride; the latter is reacted with silver trifluoromethyl sulphonate yielding azidoacetyl trifluoromethyl sulphonate; azido acetic acid, mercuric acetate and propyne form isopropenyl azido acetate, which reacts with methane sulphonic acid forming azidoacetyl methanesulphonate; methyl glycolate is phosgenated and reacted with di-pmethoxybenzylamine forming methyl (N,N-dip - methoxybenzyl) - carbamoyloxyacetate which is converted in turn to the corresponding acid and acid chloride, then to 1-diazo-3-(N,N- di - p - methoxybenzyl)carbamoyloxy-2-propanone.
[GB1424373A]
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US24427172A | 1972-04-14 | 1972-04-14 | |
| US26784672A | 1972-06-30 | 1972-06-30 | |
| US26784572A | 1972-06-30 | 1972-06-30 | |
| US29635672A | 1972-10-10 | 1972-10-10 | |
| US05/336,561 US3962224A (en) | 1972-10-10 | 1973-03-05 | Cephalosporin compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE37510L IE37510L (en) | 1973-10-14 |
| IE37510B1 true IE37510B1 (en) | 1977-08-03 |
Family
ID=27540192
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE562/73A IE37510B1 (en) | 1972-04-14 | 1973-04-10 | 7-azido-cephalosporin compounds and their preparation |
Country Status (10)
| Country | Link |
|---|---|
| JP (1) | JPS5538957B2 (en) |
| CH (1) | CH599220A5 (en) |
| DD (3) | DD107053A5 (en) |
| DE (3) | DE2365456A1 (en) |
| FR (1) | FR2182953B1 (en) |
| GB (2) | GB1424375A (en) |
| IE (1) | IE37510B1 (en) |
| IL (1) | IL41986A (en) |
| NL (1) | NL7304755A (en) |
| SE (2) | SE7513006L (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3947413A (en) * | 1972-11-13 | 1976-03-30 | Merck & Co., Inc. | 3-α-Substituted cephalosporins |
| GB2300856A (en) * | 1995-05-16 | 1996-11-20 | Pfizer Ltd | Beta-lactam preparation |
-
1973
- 1973-04-05 NL NL7304755A patent/NL7304755A/xx not_active Application Discontinuation
- 1973-04-09 IL IL41986A patent/IL41986A/en unknown
- 1973-04-10 IE IE562/73A patent/IE37510B1/en unknown
- 1973-04-10 GB GB596475A patent/GB1424375A/en not_active Expired
- 1973-04-10 GB GB1705073A patent/GB1424373A/en not_active Expired
- 1973-04-11 CH CH525173A patent/CH599220A5/xx not_active IP Right Cessation
- 1973-04-11 FR FR7313062A patent/FR2182953B1/fr not_active Expired
- 1973-04-13 DD DD170170A patent/DD107053A5/xx unknown
- 1973-04-13 DE DE2365456*A patent/DE2365456A1/en not_active Ceased
- 1973-04-13 DE DE2365582A patent/DE2365582C2/en not_active Expired
- 1973-04-13 DD DD179575*A patent/DD112272A5/xx unknown
- 1973-04-13 DD DD179995*A patent/DD112455A5/xx unknown
- 1973-04-13 DE DE2365406*A patent/DE2365406A1/en not_active Ceased
- 1973-04-14 JP JP4184973A patent/JPS5538957B2/ja not_active Expired
-
1975
- 1975-11-19 SE SE7513006A patent/SE7513006L/en unknown
- 1975-11-19 SE SE7513005A patent/SE7513005L/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DD107053A5 (en) | 1974-07-12 |
| IE37510L (en) | 1973-10-14 |
| DE2318829A1 (en) | 1973-10-31 |
| GB1424373A (en) | 1976-02-11 |
| JPS4914488A (en) | 1974-02-07 |
| DD112455A5 (en) | 1975-04-12 |
| IL41986A (en) | 1976-12-31 |
| DE2365406A1 (en) | 1975-01-23 |
| SE7513005L (en) | 1975-11-19 |
| DE2365582C2 (en) | 1982-03-25 |
| DE2318829B2 (en) | 1976-01-02 |
| DE2365582A1 (en) | 1975-06-26 |
| DD112272A5 (en) | 1975-04-05 |
| CH599220A5 (en) | 1978-05-12 |
| FR2182953B1 (en) | 1976-07-02 |
| SE7513006L (en) | 1975-11-19 |
| DE2365456A1 (en) | 1975-02-20 |
| JPS5538957B2 (en) | 1980-10-07 |
| NL7304755A (en) | 1973-10-16 |
| GB1424375A (en) | 1976-02-11 |
| FR2182953A1 (en) | 1973-12-14 |
| IL41986A0 (en) | 1973-06-29 |
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