IL41986A - Whole synthesis of cephalosporins - Google Patents
Whole synthesis of cephalosporinsInfo
- Publication number
- IL41986A IL41986A IL41986A IL4198673A IL41986A IL 41986 A IL41986 A IL 41986A IL 41986 A IL41986 A IL 41986A IL 4198673 A IL4198673 A IL 4198673A IL 41986 A IL41986 A IL 41986A
- Authority
- IL
- Israel
- Prior art keywords
- formula
- compound
- hydrogen
- methyl
- methoxy
- Prior art date
Links
- 229930186147 Cephalosporin Natural products 0.000 title claims 19
- 229940124587 cephalosporin Drugs 0.000 title claims 19
- 150000001780 cephalosporins Chemical class 0.000 title claims 6
- 238000006257 total synthesis reaction Methods 0.000 title 1
- -1 azido, amino Chemical group 0.000 claims 49
- 150000001875 compounds Chemical class 0.000 claims 40
- 229910052739 hydrogen Inorganic materials 0.000 claims 38
- 239000001257 hydrogen Substances 0.000 claims 38
- 238000000034 method Methods 0.000 claims 30
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical class CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 26
- 150000003839 salts Chemical class 0.000 claims 23
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 21
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 19
- 150000002148 esters Chemical class 0.000 claims 14
- 239000000047 product Substances 0.000 claims 14
- 230000000903 blocking effect Effects 0.000 claims 12
- 150000002431 hydrogen Chemical group 0.000 claims 11
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 11
- 238000006243 chemical reaction Methods 0.000 claims 10
- 239000002253 acid Substances 0.000 claims 8
- 125000000453 2,2,2-trichloroethyl group Chemical group [H]C([H])(*)C(Cl)(Cl)Cl 0.000 claims 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 7
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims 7
- AGIJRRREJXSQJR-UHFFFAOYSA-N 2h-thiazine Chemical compound N1SC=CC=C1 AGIJRRREJXSQJR-UHFFFAOYSA-N 0.000 claims 6
- 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 claims 6
- XAKBSHICSHRJCL-UHFFFAOYSA-N [CH2]C(=O)C1=CC=CC=C1 Chemical group [CH2]C(=O)C1=CC=CC=C1 XAKBSHICSHRJCL-UHFFFAOYSA-N 0.000 claims 6
- 125000003545 alkoxy group Chemical group 0.000 claims 6
- 239000002585 base Substances 0.000 claims 6
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 6
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims 5
- ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 claims 5
- 239000000203 mixture Substances 0.000 claims 5
- 125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 claims 5
- 239000007858 starting material Substances 0.000 claims 5
- 125000000217 alkyl group Chemical group 0.000 claims 4
- 150000001412 amines Chemical class 0.000 claims 4
- 229910052736 halogen Inorganic materials 0.000 claims 4
- 150000002367 halogens Chemical group 0.000 claims 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical group [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims 4
- 230000010933 acylation Effects 0.000 claims 3
- 238000005917 acylation reaction Methods 0.000 claims 3
- 125000005843 halogen group Chemical group 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- 230000003287 optical effect Effects 0.000 claims 3
- QLAJNZSPVITUCQ-UHFFFAOYSA-N 1,3,2-dioxathietane 2,2-dioxide Chemical compound O=S1(=O)OCO1 QLAJNZSPVITUCQ-UHFFFAOYSA-N 0.000 claims 2
- DRSHXJFUUPIBHX-UHFFFAOYSA-N COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 Chemical compound COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 DRSHXJFUUPIBHX-UHFFFAOYSA-N 0.000 claims 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 2
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims 2
- 239000003377 acid catalyst Substances 0.000 claims 2
- 125000002252 acyl group Chemical group 0.000 claims 2
- 125000004442 acylamino group Chemical group 0.000 claims 2
- 125000003277 amino group Chemical group 0.000 claims 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 239000003054 catalyst Substances 0.000 claims 2
- 239000003153 chemical reaction reagent Substances 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 230000002153 concerted effect Effects 0.000 claims 2
- 125000004185 ester group Chemical group 0.000 claims 2
- 125000001188 haloalkyl group Chemical group 0.000 claims 2
- 125000001475 halogen functional group Chemical group 0.000 claims 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 2
- 150000007529 inorganic bases Chemical class 0.000 claims 2
- 229910052751 metal Inorganic materials 0.000 claims 2
- 239000002184 metal Substances 0.000 claims 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims 2
- 229910000027 potassium carbonate Inorganic materials 0.000 claims 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims 2
- IKWLIQXIPRUIDU-ZCFIWIBFSA-N (6r)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound OC(=O)C1=CCS[C@@H]2CC(=O)N12 IKWLIQXIPRUIDU-ZCFIWIBFSA-N 0.000 claims 1
- CVRHUOVQGJXGAV-UHFFFAOYSA-N 1-hydroxysulfanyl-2-methylbenzene Chemical compound CC1=CC=CC=C1SO CVRHUOVQGJXGAV-UHFFFAOYSA-N 0.000 claims 1
- NZYLEVMJODSINC-UHFFFAOYSA-N 1-methoxypyridin-1-ium Chemical compound CO[N+]1=CC=CC=C1 NZYLEVMJODSINC-UHFFFAOYSA-N 0.000 claims 1
- YUMSFEDUCCHSIV-UHFFFAOYSA-N 2-methyl-2-methylperoxypropane Chemical compound COOC(C)(C)C YUMSFEDUCCHSIV-UHFFFAOYSA-N 0.000 claims 1
- 229930184397 7-Methoxycephalosporin Natural products 0.000 claims 1
- 229910000761 Aluminium amalgam Inorganic materials 0.000 claims 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 claims 1
- 229930182555 Penicillin Natural products 0.000 claims 1
- SGPGESCZOCHFCL-UHFFFAOYSA-N Tilisolol hydrochloride Chemical compound [Cl-].C1=CC=C2C(=O)N(C)C=C(OCC(O)C[NH2+]C(C)(C)C)C2=C1 SGPGESCZOCHFCL-UHFFFAOYSA-N 0.000 claims 1
- DBJUEJCZPKMDPA-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O DBJUEJCZPKMDPA-UHFFFAOYSA-N 0.000 claims 1
- 230000003213 activating effect Effects 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 150000001260 acyclic compounds Chemical class 0.000 claims 1
- 125000004423 acyloxy group Chemical group 0.000 claims 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 claims 1
- 150000008041 alkali metal carbonates Chemical class 0.000 claims 1
- 229910000102 alkali metal hydride Inorganic materials 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- 150000003934 aromatic aldehydes Chemical class 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- DHDCEZNLFYNPOD-SSDOTTSWSA-N carbamoyloxymethyl (6R)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound C(N)(=O)OCOC(=O)C1=CCS[C@H]2N1C(C2)=O DHDCEZNLFYNPOD-SSDOTTSWSA-N 0.000 claims 1
- 125000001589 carboacyl group Chemical group 0.000 claims 1
- 150000001721 carbon Chemical group 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims 1
- 150000001768 cations Chemical class 0.000 claims 1
- 239000007795 chemical reaction product Substances 0.000 claims 1
- BULLHNJGPPOUOX-UHFFFAOYSA-N chloroacetone Chemical compound CC(=O)CCl BULLHNJGPPOUOX-UHFFFAOYSA-N 0.000 claims 1
- 229910052802 copper Inorganic materials 0.000 claims 1
- 239000010949 copper Substances 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- SRXOCFMDUSFFAK-UHFFFAOYSA-N dimethyl peroxide Chemical compound COOC SRXOCFMDUSFFAK-UHFFFAOYSA-N 0.000 claims 1
- NALBLJLOBICXRH-UHFFFAOYSA-N dinitrogen monohydride Chemical group N=[N] NALBLJLOBICXRH-UHFFFAOYSA-N 0.000 claims 1
- 150000004678 hydrides Chemical class 0.000 claims 1
- 125000001841 imino group Chemical group [H]N=* 0.000 claims 1
- 239000012442 inert solvent Substances 0.000 claims 1
- 238000006140 methanolysis reaction Methods 0.000 claims 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 229910000510 noble metal Inorganic materials 0.000 claims 1
- 150000007530 organic bases Chemical class 0.000 claims 1
- 150000002900 organolithium compounds Chemical class 0.000 claims 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 claims 1
- 229910052763 palladium Inorganic materials 0.000 claims 1
- 150000002960 penicillins Chemical class 0.000 claims 1
- 239000008194 pharmaceutical composition 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
- XUYJLQHKOGNDPB-UHFFFAOYSA-N phosphonoacetic acid Chemical compound OC(=O)CP(O)(O)=O XUYJLQHKOGNDPB-UHFFFAOYSA-N 0.000 claims 1
- 229910052697 platinum Inorganic materials 0.000 claims 1
- 229910003446 platinum oxide Inorganic materials 0.000 claims 1
- 239000000376 reactant Substances 0.000 claims 1
- 239000011541 reaction mixture Substances 0.000 claims 1
- 238000006798 ring closing metathesis reaction Methods 0.000 claims 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 1
- 125000005537 sulfoxonium group Chemical group 0.000 claims 1
- 150000003512 tertiary amines Chemical class 0.000 claims 1
- LWRYDHOHXNQTSK-UHFFFAOYSA-N thiophene oxide Chemical compound O=S1C=CC=C1 LWRYDHOHXNQTSK-UHFFFAOYSA-N 0.000 claims 1
- 229910052727 yttrium Inorganic materials 0.000 claims 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)
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 |
|---|---|
| IL41986A0 IL41986A0 (en) | 1973-06-29 |
| IL41986A true IL41986A (en) | 1976-12-31 |
Family
ID=27540192
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL41986A IL41986A (en) | 1972-04-14 | 1973-04-09 | Whole synthesis of cephalosporins |
Country Status (10)
| Country | Link |
|---|---|
| JP (1) | JPS5538957B2 (de) |
| CH (1) | CH599220A5 (de) |
| DD (3) | DD107053A5 (de) |
| DE (3) | DE2365582C2 (de) |
| FR (1) | FR2182953B1 (de) |
| GB (2) | GB1424373A (de) |
| IE (1) | IE37510B1 (de) |
| IL (1) | IL41986A (de) |
| NL (1) | NL7304755A (de) |
| SE (2) | SE7513005L (de) |
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 GB GB1705073A patent/GB1424373A/en not_active Expired
- 1973-04-10 IE IE562/73A patent/IE37510B1/xx unknown
- 1973-04-10 GB GB596475A patent/GB1424375A/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 DE DE2365582A patent/DE2365582C2/de not_active Expired
- 1973-04-13 DE DE2365406*A patent/DE2365406A1/de not_active Ceased
- 1973-04-13 DD DD170170A patent/DD107053A5/xx unknown
- 1973-04-13 DE DE2365456*A patent/DE2365456A1/de not_active Ceased
- 1973-04-13 DD DD179995*A patent/DD112455A5/xx unknown
- 1973-04-13 DD DD179575*A patent/DD112272A5/xx unknown
- 1973-04-14 JP JP4184973A patent/JPS5538957B2/ja not_active Expired
-
1975
- 1975-11-19 SE SE7513005A patent/SE7513005L/xx unknown
- 1975-11-19 SE SE7513006A patent/SE7513006L/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IE37510B1 (en) | 1977-08-03 |
| DE2365456A1 (de) | 1975-02-20 |
| GB1424375A (en) | 1976-02-11 |
| SE7513006L (sv) | 1975-11-19 |
| JPS4914488A (de) | 1974-02-07 |
| NL7304755A (de) | 1973-10-16 |
| DD107053A5 (de) | 1974-07-12 |
| CH599220A5 (de) | 1978-05-12 |
| DD112272A5 (de) | 1975-04-05 |
| IL41986A0 (en) | 1973-06-29 |
| DE2365582A1 (de) | 1975-06-26 |
| DD112455A5 (de) | 1975-04-12 |
| DE2318829A1 (de) | 1973-10-31 |
| DE2365582C2 (de) | 1982-03-25 |
| GB1424373A (en) | 1976-02-11 |
| DE2365406A1 (de) | 1975-01-23 |
| IE37510L (en) | 1973-10-14 |
| DE2318829B2 (de) | 1976-01-02 |
| FR2182953B1 (de) | 1976-07-02 |
| JPS5538957B2 (de) | 1980-10-07 |
| SE7513005L (sv) | 1975-11-19 |
| FR2182953A1 (de) | 1973-12-14 |
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