DE2437901A1 - 2,5-dimethyl-8-isopropyl-5,6,7,8-tetrahydro-chinolin - Google Patents
2,5-dimethyl-8-isopropyl-5,6,7,8-tetrahydro-chinolinInfo
- Publication number
- DE2437901A1 DE2437901A1 DE2437901*A DE2437901A DE2437901A1 DE 2437901 A1 DE2437901 A1 DE 2437901A1 DE 2437901 A DE2437901 A DE 2437901A DE 2437901 A1 DE2437901 A1 DE 2437901A1
- Authority
- DE
- Germany
- Prior art keywords
- isopropyl
- formula
- compound
- dimethyl
- tetrahydro
- Prior art date
- Legal status (The legal status 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 status listed.)
- Pending
Links
- XTPYTCODCSCKKQ-UHFFFAOYSA-N 2,5-dimethyl-8-propan-2-yl-5,6,7,8-tetrahydroquinoline Chemical compound C1=C(C)N=C2C(C(C)C)CCC(C)C2=C1 XTPYTCODCSCKKQ-UHFFFAOYSA-N 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 5
- 239000003205 fragrance Substances 0.000 claims description 3
- 101001061807 Homo sapiens Rab-like protein 6 Proteins 0.000 claims 1
- 102100029618 Rab-like protein 6 Human genes 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 10
- FLKPEMZONWLCSK-UHFFFAOYSA-N diethyl phthalate Chemical compound CCOC(=O)C1=CC=CC=C1C(=O)OCC FLKPEMZONWLCSK-UHFFFAOYSA-N 0.000 description 8
- FUSUHKVFWTUUBE-UHFFFAOYSA-N buten-2-one Chemical compound CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 6
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- NFLGAXVYCFJBMK-BDAKNGLRSA-N (-)-menthone Chemical compound CC(C)[C@@H]1CC[C@@H](C)CC1=O NFLGAXVYCFJBMK-BDAKNGLRSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- -1 hydroxyethylene compound Chemical class 0.000 description 3
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- ZHHYXNZJDGDGPJ-BSWSSELBSA-N (2e,4e)-nona-2,4-dienal Chemical compound CCCC\C=C\C=C\C=O ZHHYXNZJDGDGPJ-BSWSSELBSA-N 0.000 description 1
- HFYPDKJHTWHBIY-UHFFFAOYSA-N 3-methyl-2-(3-oxobutyl)-6-propan-2-ylcyclohexan-1-one Chemical compound CC(C)C1CCC(C)C(CCC(C)=O)C1=O HFYPDKJHTWHBIY-UHFFFAOYSA-N 0.000 description 1
- FRLZQXRXIKQFNS-UHFFFAOYSA-N Methyl 2-octynoate Chemical compound CCCCCC#CC(=O)OC FRLZQXRXIKQFNS-UHFFFAOYSA-N 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 240000007313 Tilia cordata Species 0.000 description 1
- 240000007591 Tilia tomentosa Species 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 150000002081 enamines Chemical class 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 229930002839 ionone Natural products 0.000 description 1
- 150000002499 ionone derivatives Chemical class 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 229940067107 phenylethyl alcohol Drugs 0.000 description 1
- SATCULPHIDQDRE-UHFFFAOYSA-N piperonal Chemical compound O=CC1=CC=C2OCOC2=C1 SATCULPHIDQDRE-UHFFFAOYSA-N 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000001846 viola odorata l. leaf absolute Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B9/00—Essential oils; Perfumes
- C11B9/0069—Heterocyclic compounds
- C11B9/0092—Heterocyclic compounds containing only N as heteroatom
-
- 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
-
- 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
- C07C45/562—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with nitrogen as the only hetero atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/385—Saturated compounds containing a keto group being part of a ring
- C07C49/403—Saturated compounds containing a keto group being part of a ring of a six-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/385—Saturated compounds containing a keto group being part of a ring
- C07C49/523—Saturated compounds containing a keto group being part of a ring containing —CHO groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/04—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/54—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
- C07D241/38—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/02—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/02—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements
- C07D295/027—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring
- C07D295/033—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring with the ring nitrogen atoms directly attached to carbocyclic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Fats And Perfumes (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Quinoline Compounds (AREA)
Description
Dr. N. Α.. ?σπ der Wsrfh
Dr. Ffüi.2 LteWaf
f-ATENTAMWALTa
2437901 . 2 4. Juli 1974 -
6600/22 -002
SOOIBTB ΑΙ7ΟΖ-ΪΥΜ3 ROU R5 35RTRAND BUPONT t Paris (France)
jL5-pimethyl-8--isopropyl-5J6,7,8-tetrahydro-cl"iinolin
Die vorliegende Erfindung betrifft die neue Verbindung 2,5-Dimethyl-8-isopropyl-5,6,J,8-tetrahydrochinolin. der Formel
I
Erfindungsgemäss' kann die Verbindung der Formel I dadurch
hergestellt werden, dass 'man das Dion 1-Methyl-^-iso-
propyl-2-(5'-oxobuuyl)-cyclohexan~3-on der Pornel
.0
II
mit einer: Hydroxylamirisalz, vorzugsweise mit einen Hydroxy1-aminhydrchalogenid,
wie Hydroxylaminhydrochlorid, behandelt.
Das Dion Ίΐ kann seinerseits aus p-Menthcn (ill) über
das Enarnin .rv auf an sich bekannte Art erhalten werden,
III s
TV
z.B. durch Umsetzung des Ketons III'mit Pyrrolidin in Gegen
wart eines sauren Katalysators,.wie. p-Toluolsulfonsäure,
und Ueberführung des Enamins IV mit Methylvinylketon in
das Dion II . ■ ·
■Das Dion II kann auch im Sinne des nachstehenden Schemas
.CHOH
VI .
durch umsetzung der Hydroxysethyl-enverbindung . Y mit Methylvinylketon
und anschliessende Lei"orr.ylierung der Verbindung
VI erhalten werden.
Die erfindungsgenässe Verbindung^ der Formel I.-zeichnet
sich durch wertvolle geruchliche Eigenschaften aus und kam: de;r.gesäss als. Riechstoff- verwendet
irerden, wie z.B. nur Herstellung von Riechstoffkospositionen,
wie-Parfüms. Das-Chinolinderivat der Formel I hat einen
würzigen, leicht ambraartifren Geruch mit Lindennote.
Ί
NACHGERE[QHT|
2 g l-Methyl-4-isopropyl-2-(3'-oxobutyl)-cyclohexan-3-on,
1,2 g Hydroxylaminhydrochlorid und 1OÖ ml Aethanol werden
in einen 2 50 ml Autoklaven gegeben. Der Autoklav wird während 5 Stunden auf 1500C erhitzt. Hierauf wird das Aethanol abdestilliert
und der Rückstand in 40 ml 20%iger Kaliumhydroxydlösung aufgenommen. Das Gemisch wird mit Diäthylather extrahiert
der Extrakt über Natriumsulfat getrocknet und der Aether anschließend abdestilliert. Der Rückstand wird über
eine Silicagelkolonne (Partikel 0,05 bis 0,2 mm) unter Verwendung von CHCl, als Eluiermittel gereinigt. Durch
Destillation erhält man 2,5-Dimethyl-8-isopropyl-5,6 ,7,8-tetrahydrochinolin
(Formel IV) mit einem Siedepunkt von 7O-72°C/O,4 mm Hg.
Das Ausgangsmaterial kann wie folgt hergestellt werden:
a) 77 g p-Menthon, 35 g Pyrrolidin und 0,8 g p-Toluolsulfonsäure
werden in 400 ml wasserfreiem Benzol gelöst. Das Gemisch wird 10 Stunden am Rückfluss erhitzt.
ZU dem Zeitpunkt, wo die weitere Zugabe von p-Toluolsulfonsäure
keine weitere Wasserabspaltung mehr hervorruft, wird das Benzol abdestilliert und der Rückstand im Vakuum fraktioniert.
Man erhält das Pyrrolidin-enamin des p-Menthons (XIII) mit einem Siedepunkt von 8O-82°C. Ausbeute 2 8%.
b) Ein Gemisch von 19,6 g Pyrrolidin-enamin des p-Menthons, 10 ml Methylvinylketon und 150 ml wasserfreies
Benzol wird 20 Stunden unter Stickstoff am Rückfluss erhitzt. Das Gemisch wird dann abgekühlt und mit
m 6g Natriumacetat in 12 ml Wasser sowie mit 12 ml Essig-
° säure versetzt. Das Gemisch wird nochmals 4 Stunden Θ& am Rückfluss erhitzt. Dann wird das Produkt mit Benzol
=■ H —
extrahiert und das Lösungsmittel abgedampft. Der Rückstand
wird im Vakuum fraktioniert und man erhält l-Methyl-4-isopropyl-2-(3'-oxobutyl)-cyclohexan-3-on
mit einem Siedepunkt von 88-9O°C.
Beispiel A
(Lindeninfusion)
(Lindeninfusion)
Gewichtsteile
HydroxyeitroneIlal 250
Kristallisiertes Heliotropin 50
Phenyläthylalkohol 80
Jonon 100% (5% in Aethylphthalat 150
Nonadienal 150
Veilchenblätter-Absolue (1% in Aethylphthalat 100
Methylheptincarbonat (10% in Aethylphthalat 20
Aethylphthalat 100 2,5-Dimethyl-8-isopropyl-5,6,7,8-tetra-
hydrochinolin 100
1000
5Ö9824/Ö916
Claims (1)
- • 207901Patentansprüche1« Ύ&τfahren z.ur Serstellung; von 2,5-BImethyl-8-isoprop;r-l' 5,6,7,8-tetpahydrochinolin der Formeldaetar-eli gekennzeichnet, dass man das Dion l-Metliyl-4—isopropyl—2-- (3 "-Mit einea Eyärostjlasinsalz behandelt.^clohexaii-3-ctn.'2* Yei-fatorem stcc Parf&aierpjag; von ErodtEkteB., gekerffiizeiebnett dass laan diesea'eine Verbiiidiisg der Formel I3. Riechstofj^GssTOsitioEnen, an einer Yerbindning der Morsel ΐeinenVerwendung von einer Verbindung der Formel Ials Riechstoff.5« Die Verbindung der Formel Io. 2, 5-Binöthyl-8~isopropyl-5 * 617»8-te trahydrochlncli.i509824/0316
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH430173A CH579912A5 (de) | 1973-03-22 | 1973-03-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2437901A1 true DE2437901A1 (de) | 1975-06-12 |
Family
ID=4273531
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2437900*A Pending DE2437900A1 (de) | 1973-03-22 | 1974-03-19 | Pinanopyrazole |
| DE2413153A Pending DE2413153A1 (de) | 1973-03-22 | 1974-03-19 | Heterocyclische verbindungen |
| DE2437901*A Pending DE2437901A1 (de) | 1973-03-22 | 1974-03-19 | 2,5-dimethyl-8-isopropyl-5,6,7,8-tetrahydro-chinolin |
Family Applications Before (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2437900*A Pending DE2437900A1 (de) | 1973-03-22 | 1974-03-19 | Pinanopyrazole |
| DE2413153A Pending DE2413153A1 (de) | 1973-03-22 | 1974-03-19 | Heterocyclische verbindungen |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3954794A (de) |
| JP (1) | JPS49126670A (de) |
| BE (1) | BE812672A (de) |
| CH (1) | CH579912A5 (de) |
| DE (3) | DE2437900A1 (de) |
| FR (3) | FR2225428B1 (de) |
| NL (1) | NL7403747A (de) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2011161163A1 (en) | 2010-06-22 | 2011-12-29 | Givaudan Sa | Organic compounds |
| CN102946741A (zh) * | 2010-06-22 | 2013-02-27 | 奇华顿股份有限公司 | 有机化合物 |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3023722A1 (de) * | 1980-06-25 | 1982-01-21 | Basf Ag, 6700 Ludwigshafen | Neue pigmentform des (beta) -kupferphthalocyanins und dessen verwendung |
| US6248343B1 (en) | 1998-01-20 | 2001-06-19 | Ethicon, Inc. | Therapeutic antimicrobial compositions |
| DE10105031A1 (de) * | 2001-02-05 | 2002-08-14 | Bosch Gmbh Robert | Vorrichtung zur Dämpfung von Druckpulsationen in Hochdruckeinspritzsystemen |
| TWI278504B (en) * | 2003-11-04 | 2007-04-11 | Lg Chemical Ltd | New compound capable of being used in organic layer of organic light emitting device |
| RU2409448C2 (ru) * | 2006-07-07 | 2011-01-20 | Ротелек | Способ непрерывного литья плоских металлических изделий с электромагнитным перемешиванием и установка для его осуществления |
| CN103159676B (zh) * | 2011-12-16 | 2015-07-15 | 卢忠林 | 一种式i化合物的制备方法 |
| EP2851415B1 (de) * | 2012-03-27 | 2016-04-27 | International Flavors & Fragrances Inc. | Neuartige Chinazolinderivate und deren Verwendung in Parfümzusammensetzungen |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3691179A (en) * | 1970-07-31 | 1972-09-12 | Ciba Geigy Corp | Cycloalkano (c)pyrazole-3-acids |
| US3691180A (en) * | 1970-07-31 | 1972-09-12 | Ciba Geigy Corp | Cycloalkano (c)pyrazoles |
-
1973
- 1973-03-22 CH CH430173A patent/CH579912A5/xx not_active IP Right Cessation
-
1974
- 1974-03-18 US US05/452,349 patent/US3954794A/en not_active Expired - Lifetime
- 1974-03-19 JP JP49031405A patent/JPS49126670A/ja active Pending
- 1974-03-19 DE DE2437900*A patent/DE2437900A1/de active Pending
- 1974-03-19 DE DE2413153A patent/DE2413153A1/de active Pending
- 1974-03-19 DE DE2437901*A patent/DE2437901A1/de active Pending
- 1974-03-20 NL NL7403747A patent/NL7403747A/xx unknown
- 1974-03-21 FR FR7409745A patent/FR2225428B1/fr not_active Expired
- 1974-03-22 BE BE142312A patent/BE812672A/xx unknown
- 1974-08-13 FR FR7428102A patent/FR2241547B1/fr not_active Expired
- 1974-08-13 FR FR7428104A patent/FR2270244B1/fr not_active Expired
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2011161163A1 (en) | 2010-06-22 | 2011-12-29 | Givaudan Sa | Organic compounds |
| CN102946741A (zh) * | 2010-06-22 | 2013-02-27 | 奇华顿股份有限公司 | 有机化合物 |
| CN102946741B (zh) * | 2010-06-22 | 2014-05-14 | 奇华顿股份有限公司 | 有机化合物 |
| US8933231B2 (en) | 2010-06-22 | 2015-01-13 | Givaudan Sa | Organic compounds |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2270244B1 (de) | 1978-01-27 |
| FR2225428B1 (de) | 1979-09-21 |
| JPS49126670A (de) | 1974-12-04 |
| DE2413153A1 (de) | 1974-11-07 |
| US3954794A (en) | 1976-05-04 |
| DE2437900A1 (de) | 1975-04-30 |
| NL7403747A (de) | 1974-09-24 |
| FR2241547A1 (de) | 1975-03-21 |
| FR2225428A1 (de) | 1974-11-08 |
| CH579912A5 (de) | 1976-09-30 |
| FR2270244A1 (de) | 1975-12-05 |
| FR2241547B1 (de) | 1978-06-16 |
| BE812672A (fr) | 1974-09-23 |
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