IL27271A - Isoprenoid compounds and process for the manufacture thereof - Google Patents

Isoprenoid compounds and process for the manufacture thereof

Info

Publication number: IL27271A
Authority: IL; Israel
Prior art keywords: formula; lower alkyl; compound; represents lower; aldehyde
Prior art date: 1966-01-28

Application number

IL27271A

Other languages

English (en)

Original Assignee

Hoffmann La Roche

Sparamedica 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.)

1966-01-28

Filing date

1967-01-18

Publication date

1971-04-28

1967-01-18 Application filed by Hoffmann La Roche, Sparamedica Ag filed Critical Hoffmann La Roche

1971-04-28 Publication of IL27271A publication Critical patent/IL27271A/en

Links

238000000034 method Methods 0.000 title claims description 13
-1 Isoprenoid compounds Chemical class 0.000 title claims description 11
238000004519 manufacturing process Methods 0.000 title claims description 4
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 13
125000000217 alkyl group Chemical group 0.000 claims description 8
150000001875 compounds Chemical class 0.000 claims description 7
239000003513 alkali Substances 0.000 claims description 6
150000001408 amides Chemical class 0.000 claims description 6
125000003545 alkoxy group Chemical group 0.000 claims description 5
BWKDLDWUVLGWFC-UHFFFAOYSA-N calcium;azanide Chemical compound [NH2-].[NH2-].[Ca+2] BWKDLDWUVLGWFC-UHFFFAOYSA-N 0.000 claims description 4
229910052739 hydrogen Inorganic materials 0.000 claims description 4
239000001257 hydrogen Substances 0.000 claims description 4
125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 claims description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
AFRJJFRNGGLMDW-UHFFFAOYSA-N lithium amide Chemical compound [Li+].[NH2-] AFRJJFRNGGLMDW-UHFFFAOYSA-N 0.000 claims description 3
239000002904 solvent Substances 0.000 claims description 3
150000001299 aldehydes Chemical class 0.000 claims 4
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 3
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 2
239000000126 substance Substances 0.000 claims 2
KDOAHVPFGIYCEU-UHFFFAOYSA-N 3-ethoxy-2-methylprop-2-enal Chemical compound CCOC=C(C)C=O KDOAHVPFGIYCEU-UHFFFAOYSA-N 0.000 claims 1
RXVCZRFZUPUIQQ-UHFFFAOYSA-N 5-(2-methoxypropan-2-yloxy)-3-methylpent-3-en-1-yne Chemical compound COC(C)(C)OCC=C(C)C#C RXVCZRFZUPUIQQ-UHFFFAOYSA-N 0.000 claims 1
150000002431 hydrogen Chemical class 0.000 claims 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 1
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 6
229910052744 lithium Inorganic materials 0.000 description 6
239000000203 mixture Substances 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
229910021529 ammonia Inorganic materials 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 5
238000009833 condensation Methods 0.000 description 5
230000005494 condensation Effects 0.000 description 5
239000007788 liquid Substances 0.000 description 5
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
150000001412 amines Chemical class 0.000 description 3
239000007858 starting material Substances 0.000 description 3
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 2
238000006359 acetalization reaction Methods 0.000 description 2
229960000583 acetic acid Drugs 0.000 description 2
239000002253 acid Substances 0.000 description 2
238000001816 cooling Methods 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 2
229910052742 iron Inorganic materials 0.000 description 2
229910052751 metal Inorganic materials 0.000 description 2
239000002184 metal Substances 0.000 description 2
150000004291 polyenes Chemical class 0.000 description 2
238000003756 stirring Methods 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
YKLWPGCWVBBCTO-UHFFFAOYSA-N 1-ethenoxyprop-1-ene Chemical compound CC=COC=C YKLWPGCWVBBCTO-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
239000005695 Ammonium acetate Substances 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
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 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
150000001241 acetals Chemical class 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
150000001341 alkaline earth metal compounds Chemical class 0.000 description 1
229940043376 ammonium acetate Drugs 0.000 description 1
235000019257 ammonium acetate Nutrition 0.000 description 1
235000019270 ammonium chloride Nutrition 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
238000009835 boiling Methods 0.000 description 1
FUSUHKVFWTUUBE-UHFFFAOYSA-N buten-2-one Chemical compound CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000004040 coloring Methods 0.000 description 1
239000002537 cosmetic Substances 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
150000002440 hydroxy compounds Chemical class 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
238000002955 isolation Methods 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
239000000155 melt Substances 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
239000012071 phase Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
239000001117 sulphuric acid Substances 0.000 description 1
235000011149 sulphuric acid Nutrition 0.000 description 1
239000012485 toluene extract Substances 0.000 description 1

Classifications

- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/14—Preparation of carboxylic acid esters from carboxylic acid halides
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/28—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group
- C07C67/283—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group by hydrogenation of unsaturated carbon-to-carbon bonds

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Oil, Petroleum & Natural Gas (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Coloring Foods And Improving Nutritive Qualities (AREA)
Pyrane Compounds (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

IL27271A 1966-01-28 1967-01-18 Isoprenoid compounds and process for the manufacture thereof IL27271A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH123266A CH468330A (de)	1966-01-28	1966-01-28	Verfahren zur Herstellung von isoprenoiden Verbindungen

Publications (1)

Publication Number	Publication Date
IL27271A true IL27271A (en)	1971-04-28

Family

ID=4205567

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL27271A IL27271A (en)	1966-01-28	1967-01-18	Isoprenoid compounds and process for the manufacture thereof

Country Status (12)

Country	Link
US (1)	US3687990A (de)
JP (1)	JPS5019530B1 (de)
BE (1)	BE693072A (de)
CH (1)	CH468330A (de)
DE (1)	DE1568805A1 (de)
ES (1)	ES336151A1 (de)
FR (1)	FR1506896A (de)
GB (2)	GB1153924A (de)
IL (1)	IL27271A (de)
NL (1)	NL6700714A (de)
SE (1)	SE354465B (de)
YU (1)	YU31653B (de)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3919329A (en) *	1974-04-25	1975-11-11	Zoecon Corp	Synthesis of the pink bollworm sex pheromone
JPS5770892U (de) *	1980-10-16	1982-04-28
JPS5943190U (ja) *	1982-09-17	1984-03-21	株式会社大平	ノツク式ペンシルのノツク冠
US7759506B2 (en) *	2002-02-25	2010-07-20	Diffusion Pharmaceuticals Llc	Bipolar trans carotenoid salts and their uses
PL373780A1 (en) *	2002-02-25	2005-09-19	Diffusion Pharmaceuticals Llc	Bipolar trans carotenoid salts and their uses
WO2006104610A2 (en)	2005-02-24	2006-10-05	Diffusion Pharmaceuticals Llc	Trans carotenoids, their synthesis, formulation and uses
AU2008246305B2 (en) *	2007-04-13	2013-03-21	Diffusion Pharmaceuticals Llc	Use of bipolar trans carotenoids as a pretreatment and in the treatment of peripheral vascular disease
WO2009058399A1 (en) *	2007-10-31	2009-05-07	Diffusion Pharmaceuticals Llc	A new class of therapeutics that enhance small molecule diffusion
EP3539542B1 (de)	2009-06-22	2023-04-19	Diffusion Pharmaceuticals LLC	Verteilungsverbesserte verbindungen und ihre verwendung mit einem thrombolyticum
AU2011262361A1 (en)	2010-06-02	2013-01-10	Diffusion Pharmaceuticals Llc	Oral formulations of bipolar trans carotenoids
US11185523B2 (en)	2016-03-24	2021-11-30	Diffusion Pharmaceuticals Llc	Use of bipolar trans carotenoids with chemotherapy and radiotherapy for treatment of cancer

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3489806A (en) *	1967-01-19	1970-01-13	Hoffmann La Roche	Isoprenoid compounds and a process for producing the same

1966
- 1966-01-28 CH CH123266A patent/CH468330A/de unknown
- 1966-12-13 DE DE19661568805 patent/DE1568805A1/de active Pending
- 1966-12-29 FR FR89266A patent/FR1506896A/fr not_active Expired
1967
- 1967-01-11 YU YU0041/67A patent/YU31653B/xx unknown
- 1967-01-17 NL NL6700714A patent/NL6700714A/xx unknown
- 1967-01-18 IL IL27271A patent/IL27271A/en unknown
- 1967-01-24 BE BE693072D patent/BE693072A/xx unknown
- 1967-01-26 JP JP674835A patent/JPS5019530B1/ja active Pending
- 1967-01-27 ES ES336151A patent/ES336151A1/es not_active Expired
- 1967-01-27 GB GB60559/68A patent/GB1153924A/en not_active Expired
- 1967-01-27 GB GB4190/67A patent/GB1153923A/en not_active Expired
- 1967-01-27 SE SE01235/67A patent/SE354465B/xx unknown
1969
- 1969-07-01 US US838305A patent/US3687990A/en not_active Expired - Lifetime

Also Published As

Publication number	Publication date
YU31653B (en)	1973-10-31
DE1568805A1 (de)	1970-04-02
ES336151A1 (es)	1968-04-01
NL6700714A (de)	1967-07-31
CH468330A (de)	1969-02-15
FR1506896A (fr)	1967-12-22
GB1153924A (en)	1969-06-04
YU4167A (en)	1973-04-30
JPS5019530B1 (de)	1975-07-08
US3687990A (en)	1972-08-29
BE693072A (de)	1967-07-24
SE354465B (de)	1973-03-12
GB1153923A (en)	1969-06-04

Publication	Publication Date	Title
Hardtmann et al.	1975	The chemistry of 2H‐3, 1‐benzoxazine‐2, 4 (1H) dione (isatoic anhydrides) 1. The synthesis of N‐substituted 2H‐3, 1‐benzoxazine‐2, 4 (1H) diones
IL27271A (en)	1971-04-28	Isoprenoid compounds and process for the manufacture thereof
Santucci et al.	1958	Some Bromine-containing and Sulfur-containing Aromatic Bornic Acids
US3687944A (en)	1972-08-29	Process for the preparation of bufalin and related compounds
Klunder et al.	1972	Chemistry of strained polycyclic compounds—III: Synthesis of cubane and homocubane alcohols
NO140101B (no)	1979-03-26	Fremgangsmaate til fremstilling av substituerte aminobenzosyrederivater
US3413288A (en)	1968-11-26	Process for the production of steroidal c-17 spirolactones
US4997957A (en)	1991-03-05	Process for the production of thiotetronic acid
Mehra et al.	1967	Terpenoids—CV: Transformation products of alantolactones
US3506652A (en)	1970-04-14	Process for the production of steroidal lactone compounds and intermediates thereof
KATO et al.	1979	Studies on Ketene and Its Derivatives. XCV. Reaction of Diketene with Acyl Azides
SU472506A3 (ru)	1975-05-30	Способ получени производных морфолина
SU688497A1 (ru)	1979-09-30	Способ получени 2,2,5,5-тетраметилпирролидин-1-оксил-3-карбоновой кислоты или ее амида
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US3390188A (en)	1968-06-25	Processes for the production of gamma-chloro-gamma-acetylpropanol
US2870164A (en)	1959-01-20	Process for making d, l-methysticin and d, l-dihydromethysticin
US2744137A (en)	1956-05-01	Process for the manufacture of n-methyl-beta-cyclohexen-(1)-ylethylamine
CH481088A (de)	1969-11-15	Verfahren zur Herstellung eines isoprenoiden Alkohols
US2811531A (en)	1957-10-29	Lipol and process of preparing the same
US3454626A (en)	1969-07-08	Racemic monocarboxylic acid resolution using dehydroabietylamine
US2971009A (en)	1961-02-07	3, 7-dioxygenated 3alpha-methyl-3-benz[e]indanecarboxylic acids and lactones
US4061668A (en)	1977-12-06	Process for the preparation of 2-(4-isobutylphenyl)-propiohydroxamic acid
US3376295A (en)	1968-04-02	Preparation of 3-keto-delta4-19-nor steroids
US4078085A (en)	1978-03-07	3-Aminomethyl-4-homoisotwistane and its salt and process for producing same
US2794836A (en)	1957-06-04	Process for producing nitroacetophenone compounds