CH374981A - Verfahren zur Herstellung von Sulfonylharnstoffen - Google Patents

Verfahren zur Herstellung von Sulfonylharnstoffen

Info

Publication number: CH374981A
Authority: CH; Switzerland
Prior art keywords: acid; sodium; radical; reaction; chloramide
Prior art date: 1958-06-10

Application number

CH6613058A

Other languages

German (de)

English (en)

Inventor

Walter Dr Aumueller

Herr Heinz

Original Assignee

Hoechst Ag

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1958-06-10

Filing date

1958-11-13

Publication date

1964-02-15

1958-11-13 Application filed by Hoechst Ag filed Critical Hoechst Ag

1964-02-15 Publication of CH374981A publication Critical patent/CH374981A/de

Links

238000000034 method Methods 0.000 title claims description 17
229940100389 Sulfonylurea Drugs 0.000 title claims description 8
238000002360 preparation method Methods 0.000 title claims description 6
-1 phenoxyphenyl Chemical group 0.000 claims description 25
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 6
125000001931 aliphatic group Chemical group 0.000 claims description 4
150000001447 alkali salts Chemical class 0.000 claims description 4
150000003857 carboxamides Chemical class 0.000 claims description 4
125000000217 alkyl group Chemical group 0.000 claims description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
125000003545 alkoxy group Chemical group 0.000 claims description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
239000004305 biphenyl Substances 0.000 claims description 2
235000010290 biphenyl Nutrition 0.000 claims description 2
125000004432 carbon atom Chemical group C* 0.000 claims description 2
125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 2
125000000753 cycloalkyl group Chemical group 0.000 claims description 2
229910052760 oxygen Inorganic materials 0.000 claims description 2
239000001301 oxygen Substances 0.000 claims description 2
125000003884 phenylalkyl group Chemical group 0.000 claims description 2
ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 2
229920006395 saturated elastomer Polymers 0.000 claims description 2
125000004417 unsaturated alkyl group Chemical group 0.000 claims description 2
125000006267 biphenyl group Chemical group 0.000 claims 1
238000006243 chemical reaction Methods 0.000 description 21
229910001868 water Inorganic materials 0.000 description 20
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 14
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
239000000243 solution Substances 0.000 description 11
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
239000000047 product Substances 0.000 description 8
229910000029 sodium carbonate Inorganic materials 0.000 description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
239000000706 filtrate Substances 0.000 description 7
239000012948 isocyanate Substances 0.000 description 7
SANOUVWGPVYVAV-UHFFFAOYSA-N isovaleramide Chemical compound CC(C)CC(N)=O SANOUVWGPVYVAV-UHFFFAOYSA-N 0.000 description 7
235000017550 sodium carbonate Nutrition 0.000 description 7
DAULHAZHIILZEA-UHFFFAOYSA-N [Na].NCl.C1(=CC=C(C=C1)S(=O)(=O)O)C Chemical compound [Na].NCl.C1(=CC=C(C=C1)S(=O)(=O)O)C DAULHAZHIILZEA-UHFFFAOYSA-N 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
XWGJFPHUCFXLBL-UHFFFAOYSA-M rongalite Chemical compound [Na+].OCS([O-])=O XWGJFPHUCFXLBL-UHFFFAOYSA-M 0.000 description 6
JTDKEDJPCUTMJL-UHFFFAOYSA-N 1-(4-methylphenyl)sulfonyl-3-(2-methylpropyl)urea Chemical compound CC(C)CNC(=O)NS(=O)(=O)C1=CC=C(C)C=C1 JTDKEDJPCUTMJL-UHFFFAOYSA-N 0.000 description 5
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 5
229910021529 ammonia Inorganic materials 0.000 description 5
150000002513 isocyanates Chemical class 0.000 description 5
238000002844 melting Methods 0.000 description 5
230000008018 melting Effects 0.000 description 5
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
229910052783 alkali metal Inorganic materials 0.000 description 4
238000010438 heat treatment Methods 0.000 description 4
239000000155 melt Substances 0.000 description 4
239000011734 sodium Substances 0.000 description 4
SBOYIDYZPREUQJ-UHFFFAOYSA-N 1-methyl-3-(4-methylphenyl)sulfonylurea Chemical compound CNC(=O)NS(=O)(=O)C1=CC=C(C)C=C1 SBOYIDYZPREUQJ-UHFFFAOYSA-N 0.000 description 3
150000001408 amides Chemical class 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
238000001556 precipitation Methods 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
LMYRWZFENFIFIT-UHFFFAOYSA-N toluene-4-sulfonamide Chemical compound CC1=CC=C(S(N)(=O)=O)C=C1 LMYRWZFENFIFIT-UHFFFAOYSA-N 0.000 description 3
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
QSLBKVNCTRJJNT-UHFFFAOYSA-N 1-(4-methylphenyl)sulfonyl-3-propylurea Chemical compound CCCNC(=O)NS(=O)(=O)C1=CC=C(C)C=C1 QSLBKVNCTRJJNT-UHFFFAOYSA-N 0.000 description 2
TYCNEYCZTJHLJI-UHFFFAOYSA-N 1-benzyl-3-(4-methylphenyl)sulfonylurea Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)NCC1=CC=CC=C1 TYCNEYCZTJHLJI-UHFFFAOYSA-N 0.000 description 2
NNZVKALEGZPYKL-UHFFFAOYSA-N 1-isocyanato-2-methylpropane Chemical compound CC(C)CN=C=O NNZVKALEGZPYKL-UHFFFAOYSA-N 0.000 description 2
LSBDFXRDZJMBSC-UHFFFAOYSA-N 2-phenylacetamide Chemical compound NC(=O)CC1=CC=CC=C1 LSBDFXRDZJMBSC-UHFFFAOYSA-N 0.000 description 2
235000008733 Citrus aurantifolia Nutrition 0.000 description 2
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 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
235000011941 Tilia x europaea Nutrition 0.000 description 2
239000002253 acid Substances 0.000 description 2
DNSISZSEWVHGLH-UHFFFAOYSA-N butanamide Chemical compound CCCC(N)=O DNSISZSEWVHGLH-UHFFFAOYSA-N 0.000 description 2
150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
150000001875 compounds Chemical class 0.000 description 2
238000001816 cooling Methods 0.000 description 2
239000013078 crystal Substances 0.000 description 2
MFNYBOWJWGPXFM-UHFFFAOYSA-N cyclobutanecarboxamide Chemical compound NC(=O)C1CCC1 MFNYBOWJWGPXFM-UHFFFAOYSA-N 0.000 description 2
238000005187 foaming Methods 0.000 description 2
RIGBPMDIGYBTBJ-UHFFFAOYSA-N glycyclamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)NC1CCCCC1 RIGBPMDIGYBTBJ-UHFFFAOYSA-N 0.000 description 2
125000005843 halogen group Chemical group 0.000 description 2
239000004571 lime Substances 0.000 description 2
239000000203 mixture Substances 0.000 description 2
239000004570 mortar (masonry) Substances 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
239000007858 starting material Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
DEVUYWTZRXOMSI-UHFFFAOYSA-N (sulfamoylamino)benzene Chemical compound NS(=O)(=O)NC1=CC=CC=C1 DEVUYWTZRXOMSI-UHFFFAOYSA-N 0.000 description 1
PVFQXLVHJBFKHG-UHFFFAOYSA-N 1-(2-methylpropyl)cyclohexane-1-carboxamide Chemical compound CC(C)CC1(C(N)=O)CCCCC1 PVFQXLVHJBFKHG-UHFFFAOYSA-N 0.000 description 1
GEENOMDCQXABNR-UHFFFAOYSA-N 1-(3,4-dimethylphenyl)sulfonyl-3-(2-methylpropyl)urea Chemical compound CC=1C=C(C=CC=1C)S(=O)(=O)NC(=O)NCC(C)C GEENOMDCQXABNR-UHFFFAOYSA-N 0.000 description 1
FSMXHJWUKJCMQI-UHFFFAOYSA-N 1-cyclobutyl-3-(4-methylphenyl)sulfonylurea Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)NC1CCC1 FSMXHJWUKJCMQI-UHFFFAOYSA-N 0.000 description 1
ICBQXEWYZVQCFH-UHFFFAOYSA-N 3-(4-bromoanilino)-n,n-dimethylpropanamide Chemical class CN(C)C(=O)CCNC1=CC=C(Br)C=C1 ICBQXEWYZVQCFH-UHFFFAOYSA-N 0.000 description 1
VUYFJZVCVCYCJT-UHFFFAOYSA-N 4-methylbenzenesulfonamide;sodium Chemical compound [Na].CC1=CC=C(S(N)(=O)=O)C=C1 VUYFJZVCVCYCJT-UHFFFAOYSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical class [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical class NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 1
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
235000013832 Valeriana officinalis Nutrition 0.000 description 1
244000126014 Valeriana officinalis Species 0.000 description 1
XCFZFZHFLHHWOY-UHFFFAOYSA-N [Na].C1(=CC=CC=C1)S(=O)(=O)Cl Chemical compound [Na].C1(=CC=CC=C1)S(=O)(=O)Cl XCFZFZHFLHHWOY-UHFFFAOYSA-N 0.000 description 1
FCCWAECUNYGHFL-UHFFFAOYSA-N [Na].NBr.C1(=CC=C(C=C1)S(=O)(=O)O)C Chemical compound [Na].NBr.C1(=CC=C(C=C1)S(=O)(=O)O)C FCCWAECUNYGHFL-UHFFFAOYSA-N 0.000 description 1
DQSCNRIAQYOTPV-UHFFFAOYSA-N [Na].NCl.CC1=C(C(=CC=C1)Cl)S(=O)(=O)O Chemical compound [Na].NCl.CC1=C(C(=CC=C1)Cl)S(=O)(=O)O DQSCNRIAQYOTPV-UHFFFAOYSA-N 0.000 description 1
239000003513 alkali Substances 0.000 description 1
229940125708 antidiabetic agent Drugs 0.000 description 1
239000003472 antidiabetic agent Substances 0.000 description 1
238000013459 approach Methods 0.000 description 1
239000012736 aqueous medium Substances 0.000 description 1
150000001540 azides Chemical class 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
239000008280 blood Substances 0.000 description 1
210000004369 blood Anatomy 0.000 description 1
239000004202 carbamide Substances 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
239000012043 crude product Substances 0.000 description 1
PNZXMIKHJXIPEK-UHFFFAOYSA-N cyclohexanecarboxamide Chemical compound NC(=O)C1CCCCC1 PNZXMIKHJXIPEK-UHFFFAOYSA-N 0.000 description 1
AIMMVWOEOZMVMS-UHFFFAOYSA-N cyclopropanecarboxamide Chemical compound NC(=O)C1CC1 AIMMVWOEOZMVMS-UHFFFAOYSA-N 0.000 description 1
238000004200 deflagration Methods 0.000 description 1
238000006731 degradation reaction Methods 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000007789 gas Substances 0.000 description 1
DBBRJAWSDTYYBM-UHFFFAOYSA-N isocyanatocyclopropane Chemical compound O=C=NC1CC1 DBBRJAWSDTYYBM-UHFFFAOYSA-N 0.000 description 1
239000007788 liquid Substances 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
VBTQNRFWXBXZQR-UHFFFAOYSA-N n-bromoacetamide Chemical compound CC(=O)NBr VBTQNRFWXBXZQR-UHFFFAOYSA-N 0.000 description 1
HNHVTXYLRVGMHD-UHFFFAOYSA-N n-butyl isocyanate Chemical compound CCCCN=C=O HNHVTXYLRVGMHD-UHFFFAOYSA-N 0.000 description 1
IPWFJLQDVFKJDU-UHFFFAOYSA-N pentanamide Chemical compound CCCCC(N)=O IPWFJLQDVFKJDU-UHFFFAOYSA-N 0.000 description 1
DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical class O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
ORQYPOUSZINNCB-UHFFFAOYSA-N potassium;hypobromite Chemical compound [K+].Br[O-] ORQYPOUSZINNCB-UHFFFAOYSA-N 0.000 description 1
QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 1
239000000376 reactant Substances 0.000 description 1
238000001226 reprecipitation Methods 0.000 description 1
238000012552 review Methods 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
229940124530 sulfonamide Drugs 0.000 description 1
150000003456 sulfonamides Chemical class 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
235000016788 valerian Nutrition 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/50—Compounds containing any of the groups, X being a hetero atom, Y being any atom
- C07C311/52—Y being a hetero atom
- C07C311/54—Y being a hetero atom either X or Y, but not both, being nitrogen atoms, e.g. N-sulfonylurea

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CH6613058A 1958-06-10 1958-11-13 Verfahren zur Herstellung von Sulfonylharnstoffen CH374981A (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DEF0025929		1958-06-10

Publications (1)

Publication Number	Publication Date
CH374981A true CH374981A (de)	1964-02-15

Family

ID=7091819

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH6613058A CH374981A (de)	1958-06-10	1958-11-13	Verfahren zur Herstellung von Sulfonylharnstoffen

Country Status (2)

Country	Link
CH (1)	CH374981A (fr)
OA (1)	OA01373A (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GR890100141A (el) *	1988-03-04	1990-01-19	Nitrokemia Ipartelepek & Magya	Μεθοδος για την παρασκευη ν-σουλφονυλ-ουριας

1958
- 1958-11-13 CH CH6613058A patent/CH374981A/de unknown
1964
- 1964-12-31 OA OA51821A patent/OA01373A/fr unknown

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GR890100141A (el) *	1988-03-04	1990-01-19	Nitrokemia Ipartelepek & Magya	Μεθοδος για την παρασκευη ν-σουλφονυλ-ουριας

Also Published As

Publication number	Publication date
OA01373A (fr)	1969-07-04

Publication	Publication Date	Title
AT207383B (de)	1960-01-25	Verfahren zur Herstellung von Sulfonylharnstoffen
CH374981A (de)	1964-02-15	Verfahren zur Herstellung von Sulfonylharnstoffen
CH392497A (de)	1965-05-31	Verfahren zur Herstellung von neuen Benzolsulfonyl-cyclohexyl-harnstoffen
DE1075588B (de)	1960-02-18	Verfahren zur Herstellung von Sulfonylharnstoffen
DE910779C (de)	1954-05-06	Verfahren zur Darstellung von N-Sulfonylharnstoffen
AT162888B (de)	1949-04-25	Verfahren zur Darstellung von neuen 4-Aminobenzolsulfonharnstoffen
DE2527157C2 (de)	1984-01-12	Verfahren zur Herstellung von 2-Formylchinoxalin-N&uarr;1&uarr;,N&uarr;4&uarr;-dioxyddimethylacetal
DE3638364A1 (de)	1988-05-19	Verfahren zur herstellung von 5-aminosalicylsaeure
AT92386B (de)	1923-04-25	Verfahren zur Darstellung von Isopropylalkylbarbitursäuren.
AT206431B (de)	1959-11-25	Verfahren zur Herstellung von Disulfamylanilinverbindungen
CH374643A (de)	1964-01-31	Verfahren zur Herstellung von Sulfonylharnstoffen
DE887653C (de)	1953-08-24	Verfahren zur Herstellung von Cyanaminen aromatischer Oxycarbonsaeuren
DE816100C (de)	1951-10-08	Verfahren zur Herstellung der Benzol-1-carbonsaeuremethylester-2-sulfinsaeure
AT239243B (de)	1965-03-25	Verfahren zur Herstellung von 2, 3-Dicyan-1, 4-dithia-anthrahydrochinon und -anthrachinon
DE2400419B2 (de)	1977-04-07	Verfahren zur herstellung von 2-alkyl- sulfinyl-6-nitrobenzothiazolen
AT200583B (de)	1958-11-10	Verfahren zur Herstellung von neuen Sulfonylurethanen
AT226729B (de)	1963-04-10	Verfahren zur Herstellung von neuen Sulfonylharnstoffen
DE1287067B (de)	1969-01-16	2-Hydroxy-4-halogen-diphenylsulfone und Verfahren zu deren Herstellung
AT352092B (de)	1979-08-27	Verfahren zur herstellung von acetoacetamid-n- sulfofluorid
AT92407B (de)	1923-05-11	Verfahren zur Darstellung von 1-Allyl-3,7-dimethylxanthin.
AT55401B (de)	1912-09-25	Verfahren zur Herstellung von Karbaminsäureestern tertiärer Alkohole.
AT215984B (de)	1961-07-10	Verfahren zur Herstellung von neuen Amino-trifluortoluol-disulfonamiden
AT205026B (de)	1959-08-25	Verfahren zur Herstellung von neuen α-Aroyl-α-(o-carboxybenzoylamino)-essigsäureestern
DE1222068B (de)	1966-08-04	Verfahren zur Herstellung von trisubstituierten 1, 2, 4-Triazolen
DE1768582A1 (de)	1971-10-28	Verfahren zur Herstellung von 2,3-Dichlor-4-butyrylphenoxyessigsaeure

CH374981A - Verfahren zur Herstellung von Sulfonylharnstoffen - Google Patents

Info

Links

Classifications

Landscapes

Applications Claiming Priority (1)

Publications (1)

Family

ID=7091819

Family Applications (1)

Country Status (2)

Cited By (1)

Cited By (1)

Also Published As

Similar Documents