IE35436B1 - Cyclopentene derivatives and a process for the manufacture thereof - Google Patents
Cyclopentene derivatives and a process for the manufacture thereofInfo
- Publication number
- IE35436B1 IE35436B1 IE858/71A IE85871A IE35436B1 IE 35436 B1 IE35436 B1 IE 35436B1 IE 858/71 A IE858/71 A IE 858/71A IE 85871 A IE85871 A IE 85871A IE 35436 B1 IE35436 B1 IE 35436B1
- Authority
- IE
- Ireland
- Prior art keywords
- group
- enyl
- reacting
- formula
- dimethylcyclopent
- Prior art date
Links
- 125000002433 cyclopentenyl group Chemical class C1(=CCCC1)* 0.000 title abstract 4
- 238000004519 manufacturing process Methods 0.000 title 1
- 238000000034 method Methods 0.000 title 1
- 239000002253 acid Substances 0.000 abstract 3
- 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 abstract 2
- LMKDBOCNOYOSCX-UHFFFAOYSA-N 5-[5,5-dimethyl-2-(2-methyl-1,3-dioxolan-2-yl)cyclopenten-1-yl]-3-methylpenta-2,4-dienal Chemical compound C1OC(C)(OC1)C1=C(C(CC1)(C)C)C=CC(=CC=O)C LMKDBOCNOYOSCX-UHFFFAOYSA-N 0.000 abstract 2
- 150000007513 acids Chemical class 0.000 abstract 2
- 150000001299 aldehydes Chemical class 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 230000009435 amidation Effects 0.000 abstract 2
- 238000007112 amidation reaction Methods 0.000 abstract 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 2
- 238000006567 deketalization reaction Methods 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- 125000004494 ethyl ester group Chemical group 0.000 abstract 2
- 238000005907 ketalization reaction Methods 0.000 abstract 2
- 125000000468 ketone group Chemical group 0.000 abstract 2
- 150000004714 phosphonium salts Chemical class 0.000 abstract 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 abstract 2
- 125000006619 (C1-C6) dialkylamino group Chemical group 0.000 abstract 1
- 208000002874 Acne Vulgaris Diseases 0.000 abstract 1
- 101000653791 Bos taurus Protein S100-A12 Proteins 0.000 abstract 1
- 201000009030 Carcinoma Diseases 0.000 abstract 1
- 201000004681 Psoriasis Diseases 0.000 abstract 1
- USQRIYUGDHHGOV-UHFFFAOYSA-M [5-[5,5-dimethyl-2-(2-methyl-1,3-dioxolan-2-yl)cyclopenten-1-yl]-3-methylpenta-2,4-dienyl]-triphenylphosphanium bromide Chemical compound [Br-].C1OC(C)(OC1)C1=C(C(CC1)(C)C)C=CC(=CC[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)C USQRIYUGDHHGOV-UHFFFAOYSA-M 0.000 abstract 1
- CHQWTQFDYAMUHI-UHFFFAOYSA-M [Cl-].C(=O)(OCC)C=C(C[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)C Chemical compound [Cl-].C(=O)(OCC)C=C(C[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)C CHQWTQFDYAMUHI-UHFFFAOYSA-M 0.000 abstract 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 abstract 1
- 206010000496 acne Diseases 0.000 abstract 1
- 150000001298 alcohols Chemical class 0.000 abstract 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 1
- -1 aralkoxycarbonyl Chemical group 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- ZIJOSLUFMCXNHW-VURMDHGXSA-N butyl (z)-3-methyl-4-oxobut-2-enoate Chemical compound CCCCOC(=O)\C=C(\C)C=O ZIJOSLUFMCXNHW-VURMDHGXSA-N 0.000 abstract 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 239000003937 drug carrier Substances 0.000 abstract 1
- 230000032050 esterification Effects 0.000 abstract 1
- 238000005886 esterification reaction Methods 0.000 abstract 1
- NJKFMYNBRXOKOL-GQCTYLIASA-N ethyl (e)-4-chloro-3-methylbut-2-enoate Chemical compound CCOC(=O)\C=C(/C)CCl NJKFMYNBRXOKOL-GQCTYLIASA-N 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 150000002500 ions Chemical class 0.000 abstract 1
- 238000007911 parenteral administration Methods 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 150000004291 polyenes Polymers 0.000 abstract 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 abstract 1
- 238000011200 topical administration Methods 0.000 abstract 1
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
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/54—Quaternary phosphonium compounds
- C07F9/5428—Acyclic unsaturated phosphonium compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/36—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal
- C07C29/38—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal by reaction with aldehydes or ketones
- C07C29/42—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal by reaction with aldehydes or ketones with compounds containing triple carbon-to-carbon bonds, e.g. with metal-alkynes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C403/00—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone
- C07C403/20—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by carboxyl groups or halides, anhydrides, or (thio)esters 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
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/29—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups
- C07C45/298—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups with manganese derivatives
-
- 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
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
- C07C45/511—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups
- C07C45/513—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups the singly bound functional group being an etherified hydroxyl group
-
- 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
- C07C45/56—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds
- C07C45/57—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom
- C07C45/59—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom in five-membered rings
-
- 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
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/527—Unsaturated compounds containing keto groups bound to rings other than six-membered aromatic rings
- C07C49/573—Unsaturated compounds containing keto groups bound to rings other than six-membered aromatic rings containing hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/527—Unsaturated compounds containing keto groups bound to rings other than six-membered aromatic rings
- C07C49/577—Unsaturated compounds containing keto groups bound to rings other than six-membered aromatic rings containing ether groups, groups, groups, or groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
- C07C51/305—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with sulfur or sulfur-containing compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/76—Unsaturated compounds containing keto groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
- C07C67/313—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by introduction of doubly bound oxygen containing functional groups, e.g. carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
- C07C67/317—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
- C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
- C07C67/343—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D317/26—Radicals substituted by doubly bound oxygen or sulfur atoms or by two such atoms singly bound to the same carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/10—Systems containing only non-condensed rings with a five-membered ring the ring being unsaturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Epoxy Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Abstract
1336324 Cyclopentene derivatives F HOFFMANN-LA ROCHE & CO AG 8 July 1971 [10 July 1970] 32112/71 Heading C2C Novel cyclopentene derivatives of the formula wherein X is CH 3 CO, 1-hydroxyethyl, CH 3 CH 2 or CH 3 , and R<SP>1</SP> is CH 2 OH, alkoxymethylene, aralkoxymethylene, alkanoyloxymethylene, aroyloxymethylene, COOH, alkoxycarbonyl, aralkoxycarbonyl, carbamoyl, mono- or di- (C 1-6 alkyl)-carbamoyl, or a N-heterocyclylcarbonyl group attached to the polyene chain through the carbonyl group, are prepared by cyclizing - cum - dehydrating a 3,7,11,11 - tetramethyl - 10,15 - dioxo -'2,4,6,8 - hexadecatetraenoic acid or alkyl or aralkyl esters thereof, or by reacting phosphonium salts of the formula in which X<SP>11</SP> is CH 2 CO (the carbonyl group of which may be ketalized) or, CH 3 or CH 3 CH 2 , Y is aryl or di-(C 1-6 alkyl)amino and Z is a halogen or hydrosulphate ion with aldehydes of the formula or by reacting aldehydes of the formula with phosphonium salts of the formula and, in any desired sequence, subjecting if desired acids so obtained to esterification or to amidation or after ketalization of any keto group which may be present, to reduction and deketalization, or subjecting if desired esters so obtained to hydrolysis of amidation, or, after ketalization of any keto group which may be present to reduction and deketalization, and, if desired, etherifying alcohols thus obtained from acids or esters, and, if desired, reducing an acetyl group X to the 1-hydroxyethyl group or to the ethyl group. 9 - [2 - (1,1 - Ethylendioxyethyl)- 5,5 - dimethylcyclopent - 1 - enyl] - 3,7 - dimethyl - 2,4,6,8,- nonatetraenoic acid ethyl ester and butyl ester are obtained by reacting (3 - ethoxycarbonyl - 2- methylprop - 2 - enyl) - triphenylphosphonium chloride with 5 - [2 - (1,1 - ethylenedioxyethyl)- 5,5 - dimethylcyclopent - 1 - enyl] - 3 - methyl- 2,4-pentadien-1-al and by reacting {5-[2-(1,1- ethylenedioxy ethyl) - 5,5 - dimethylcyclopent- 1 - enyl] - 3 - methyl - 2,4 - pentadienyl} - triphenylphosphonium bromide with 3-formylcrotonic butyl ester respectively. The above ethyl ester may also be prepared by reacting 5 - [2 - (1,1 - ethylenedioxyethyl) - 5,5 - dimethylcyclopent - 1 - enyl] - 3 - methyl - 2,4 - pentadien - 1 - al, 4 - chloro - 3 - methylcrotonic acid ethyl ester and triphenyl phosphine. Pharmaceutical compositions, suitable for enteral, parenteral or topical administration, contain the above novel cyclopentene derivatives and compatible pharmaceutical carriers. The compounds are used in the treatment of precanceroses, carcinomas, acne and psoriasis.
[GB1336324A]
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1048070A CH544057A (en) | 1970-07-10 | 1970-07-10 | Process for the preparation of polyene compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE35436L IE35436L (en) | 1972-01-10 |
| IE35436B1 true IE35436B1 (en) | 1976-02-18 |
Family
ID=4363681
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE858/71A IE35436B1 (en) | 1970-07-10 | 1971-07-06 | Cyclopentene derivatives and a process for the manufacture thereof |
Country Status (14)
| Country | Link |
|---|---|
| AT (2) | AT316507B (en) |
| BE (1) | BE769754A (en) |
| CA (1) | CA978186A (en) |
| CH (1) | CH544057A (en) |
| DE (1) | DE2132032A1 (en) |
| ES (1) | ES393090A1 (en) |
| FR (1) | FR2100887A1 (en) |
| GB (3) | GB1336326A (en) |
| HU (1) | HU162584B (en) |
| IE (1) | IE35436B1 (en) |
| IL (1) | IL37253A (en) |
| NL (1) | NL7109525A (en) |
| SE (1) | SE377560B (en) |
| ZA (1) | ZA714124B (en) |
-
1970
- 1970-07-10 CH CH1048070A patent/CH544057A/en not_active IP Right Cessation
-
1971
- 1971-06-23 ZA ZA714124A patent/ZA714124B/en unknown
- 1971-06-28 DE DE19712132032 patent/DE2132032A1/en active Pending
- 1971-07-06 IE IE858/71A patent/IE35436B1/en unknown
- 1971-07-07 IL IL37253A patent/IL37253A/en unknown
- 1971-07-08 GB GB3211271A patent/GB1336326A/en not_active Expired
- 1971-07-08 HU HUHO1391A patent/HU162584B/hu unknown
- 1971-07-08 GB GB410873A patent/GB1336325A/en not_active Expired
- 1971-07-08 GB GB3311271A patent/GB1336324A/en not_active Expired
- 1971-07-09 SE SE7108918A patent/SE377560B/xx unknown
- 1971-07-09 ES ES393090A patent/ES393090A1/en not_active Expired
- 1971-07-09 CA CA117,819A patent/CA978186A/en not_active Expired
- 1971-07-09 BE BE769754A patent/BE769754A/en unknown
- 1971-07-09 AT AT966172A patent/AT316507B/en not_active IP Right Cessation
- 1971-07-09 AT AT600171A patent/AT311935B/en not_active IP Right Cessation
- 1971-07-09 FR FR7125287A patent/FR2100887A1/fr not_active Withdrawn
- 1971-07-09 NL NL7109525A patent/NL7109525A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| HU162584B (en) | 1973-03-28 |
| BE769754A (en) | 1972-01-10 |
| SE377560B (en) | 1975-07-14 |
| GB1336326A (en) | 1973-11-07 |
| FR2100887A1 (en) | 1972-03-24 |
| IE35436L (en) | 1972-01-10 |
| GB1336324A (en) | 1973-11-07 |
| DE2132032A1 (en) | 1972-01-13 |
| AT311935B (en) | 1973-12-10 |
| CA978186A (en) | 1975-11-18 |
| ZA714124B (en) | 1972-03-29 |
| ES393090A1 (en) | 1973-08-16 |
| IL37253A0 (en) | 1971-10-20 |
| GB1336325A (en) | 1973-11-07 |
| IL37253A (en) | 1974-12-31 |
| CH544057A (en) | 1973-11-15 |
| NL7109525A (en) | 1972-01-12 |
| AT316507B (en) | 1974-07-10 |
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