JPH0592945A - ４−トランス−（ｎ−イソプロピリデンアミノ）シクロヘキサノール及びその製造方法 - Google Patents

４−トランス−（ｎ−イソプロピリデンアミノ）シクロヘキサノール及びその製造方法

Info

Publication number: JPH0592945A
Authority: JP; Japan
Prior art keywords: trans; formula; cis; cyclohexanol; isopropylideneamino
Prior art date: 1989-12-22
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

Application number

JP2412702A

Other languages

English (en)

Japanese (ja)

Inventor

Ildiko Ratz

ラーツイルデイコー

Pal Benko

ベンコーパール

Daniel Bozsing

ボージングダーニエル

Antal Tungler

トウングレルアンタル

Tibor Mathe

マーテテイボル

Lax Geoergyi Kovanyine

コバーニイネーエラクスジエルジイ

Jozsef Petro

ペトレージヨーゼフ

Ilona Sztruhar

ストルハールイロナ

Nee Donath Gyoergyi Vereczkey

ベレツケイネーエドナートジエルジイ

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Egyt Gyogyszervegyeszeti Gyar

Original Assignee

Egyt Gyogyszervegyeszeti Gyar

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.)

1989-12-22

Filing date

1990-12-21

Publication date

1993-04-16

1990-12-21 Application filed by Egyt Gyogyszervegyeszeti Gyar filed Critical Egyt Gyogyszervegyeszeti Gyar

1993-04-16 Publication of JPH0592945A publication Critical patent/JPH0592945A/ja

Status Pending legal-status Critical Current

Links

HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 title claims abstract description 9
238000002360 preparation method Methods 0.000 title description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims abstract description 34
238000000034 method Methods 0.000 claims abstract description 18
239000000126 substance Substances 0.000 claims description 30
238000004519 manufacturing process Methods 0.000 claims description 18
239000002904 solvent Substances 0.000 claims description 17
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 15
239000011541 reaction mixture Substances 0.000 claims description 14
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 10
238000006243 chemical reaction Methods 0.000 claims description 8
238000009835 boiling Methods 0.000 claims description 5
150000001875 compounds Chemical class 0.000 claims description 5
230000007062 hydrolysis Effects 0.000 claims description 5
238000006460 hydrolysis reaction Methods 0.000 claims description 5
239000012454 non-polar solvent Substances 0.000 claims description 4
150000008044 alkali metal hydroxides Chemical class 0.000 claims description 3
150000008280 chlorinated hydrocarbons Chemical class 0.000 claims description 3
239000012736 aqueous medium Substances 0.000 claims 1
JBDGDEWWOUBZPM-XYPYZODXSA-N ambroxol Chemical compound NC1=C(Br)C=C(Br)C=C1CN[C@@H]1CC[C@@H](O)CC1 JBDGDEWWOUBZPM-XYPYZODXSA-N 0.000 abstract description 13
229960005174 ambroxol Drugs 0.000 abstract description 10
210000000621 bronchi Anatomy 0.000 abstract description 3
239000003172 expectorant agent Substances 0.000 abstract description 3
230000003419 expectorant effect Effects 0.000 abstract description 3
230000003301 hydrolyzing effect Effects 0.000 abstract 1
DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 14
239000000543 intermediate Substances 0.000 description 12
239000000243 solution Substances 0.000 description 12
239000000047 product Substances 0.000 description 9
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
238000002844 melting Methods 0.000 description 6
230000008018 melting Effects 0.000 description 6
HWAFCRWGGRVEQL-UHFFFAOYSA-N n-(4-hydroxycyclohexyl)acetamide Chemical compound CC(=O)NC1CCC(O)CC1 HWAFCRWGGRVEQL-UHFFFAOYSA-N 0.000 description 6
239000007858 starting material Substances 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 4
239000002585 base Substances 0.000 description 4
239000006227 byproduct Substances 0.000 description 4
239000003054 catalyst Substances 0.000 description 4
238000000605 extraction Methods 0.000 description 4
239000000203 mixture Substances 0.000 description 4
SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 4
OCTKLEFRMHWSLP-KYZUINATSA-N C(C)(C)=N[C@@H]1CC[C@H](CC1)O Chemical compound C(C)(C)=N[C@@H]1CC[C@H](CC1)O OCTKLEFRMHWSLP-KYZUINATSA-N 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
-1 N-isopropylideneamino Chemical group 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
239000002253 acid Substances 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
238000009903 catalytic hydrogenation reaction Methods 0.000 description 2
238000005119 centrifugation Methods 0.000 description 2
239000003610 charcoal Substances 0.000 description 2
238000001816 cooling Methods 0.000 description 2
239000013078 crystal Substances 0.000 description 2
229940079593 drug Drugs 0.000 description 2
239000003814 drug Substances 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
238000001914 filtration Methods 0.000 description 2
238000001640 fractional crystallisation Methods 0.000 description 2
238000010575 fractional recrystallization Methods 0.000 description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
239000000463 material Substances 0.000 description 2
239000012046 mixed solvent Substances 0.000 description 2
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
239000012071 phase Substances 0.000 description 2
235000011056 potassium acetate Nutrition 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
238000000746 purification Methods 0.000 description 2
238000003908 quality control method Methods 0.000 description 2
239000012429 reaction media Substances 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
210000002345 respiratory system Anatomy 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
238000000926 separation method Methods 0.000 description 2
239000012265 solid product Substances 0.000 description 2
238000000638 solvent extraction Methods 0.000 description 2
238000004090 dissolution Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/02—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups
- C07C251/04—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups having carbon atoms of imino groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C251/06—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups having carbon atoms of imino groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of a saturated carbon skeleton
- C07C251/08—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups having carbon atoms of imino groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of a saturated carbon skeleton being acyclic
- 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
- C07C2601/14—The ring being saturated

Landscapes

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

JP2412702A 1989-12-22 1990-12-21 ４−トランス−（ｎ−イソプロピリデンアミノ）シクロヘキサノール及びその製造方法 Pending JPH0592945A (ja)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
HU6744/89		1989-12-22
HU896744A HU208949B (en)	1989-12-22	1989-12-22	Process for producing 4-trans-/4-isopropyliden-amino/-cyclohexanol

Publications (1)

Publication Number	Publication Date
JPH0592945A true JPH0592945A (ja)	1993-04-16

Family

ID=10971987

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP2412702A Pending JPH0592945A (ja)	1989-12-22	1990-12-21	４−トランス−（ｎ−イソプロピリデンアミノ）シクロヘキサノール及びその製造方法

Country Status (5)

Country	Link
JP (1)	JPH0592945A (de)
AT (1)	AT398969B (de)
GB (1)	GB2239242B (de)
HU (1)	HU208949B (de)
IT (1)	IT1246048B (de)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE19745529C1 (de) *	1997-10-15	1999-03-18	Great Lakes Chem Konstanz Gmbh	Verfahren zur Herstellung von trans-4-Aminocyclohexanol
DE10125883A1 (de)	2001-05-28	2002-12-12	Serumwerk Bernburg Ag	Arzneimittel enthaltend einen Effektor des Glutathionmetabolismus zusammen mit alpha-Liponsäure im Rahmen der Nierenersatztherapie
CN113402402B (zh) *	2021-06-29	2023-08-18	江西荣兴药业有限公司	低浓度废液回收反式-对氨基环己醇的方法

1989
- 1989-12-22 HU HU896744A patent/HU208949B/hu not_active IP Right Cessation
1990
- 1990-12-21 IT IT02250690A patent/IT1246048B/it active IP Right Grant
- 1990-12-21 AT AT0261890A patent/AT398969B/de not_active IP Right Cessation
- 1990-12-21 GB GB9027816A patent/GB2239242B/en not_active Expired - Fee Related
- 1990-12-21 JP JP2412702A patent/JPH0592945A/ja active Pending

Also Published As

Publication number	Publication date
AT398969B (de)	1995-02-27
HUT58281A (en)	1992-02-28
GB2239242B (en)	1993-07-21
IT9022506A0 (it)	1990-12-21
HU208949B (en)	1994-02-28
IT9022506A1 (it)	1992-06-21
HU896744D0 (en)	1990-03-28
GB9027816D0 (en)	1991-02-13
ATA261890A (de)	1994-07-15
IT1246048B (it)	1994-11-07
GB2239242A (en)	1991-06-26

Publication	Publication Date	Title
JPH0592945A (ja)	1993-04-16	４−トランス−（ｎ−イソプロピリデンアミノ）シクロヘキサノール及びその製造方法
JPH0231704B2 (de)	1990-07-16
EP1770084B1 (de)	2011-08-24	Verfahren zur herstellung von (z)-1-phenyl-1-diethylaminocarbonyl-2-aminomethylcyclopropanhydrochlorid
FR2571366A1 (fr)	1986-04-11	Procede de preparation de la l-carnitine et de ses sels
JPS6344544A (ja)	1988-02-25	ジヒドロシクロシトラ−ル及びジヒドロシクロシトラ−ルの光学活性立体異性体の製法
JP2890856B2 (ja)	1999-05-17	クアドラート酸の製造方法
US3096244A (en)	1963-07-02	Substituted butyric acid amide and analgesia
CN101565379B (zh)	2012-02-01	L-高丝氨酸盐酸盐的制备方法
CN107382753A (zh)	2017-11-24	一种高纯度盐酸利托君的制备方法
JP4205130B2 (ja)	2009-01-07	トレミフェン結晶化法
CN112573996A (zh)	2021-03-30	一种光学活性薄荷醇的制备方法
JPH04112848A (ja)	1992-04-14	結晶性バルプロン酸マグネシウムの製造方法
WO1999036389A1 (en)	1999-07-22	Purification of tramadol
JP2003137835A (ja)	2003-05-14	（ｒ）−３−ヒドロキシ−３−（２−フェニルエチル）ヘキサン酸の製造方法
CN119707770A (zh)	2025-03-28	一种合成3-氨基氮杂环丁烷-1-甲酸叔丁基酯的方法
CN116947623A (zh)	2023-10-27	洛索洛芬酸和洛索洛芬钠的制备方法
WO2025108307A1 (zh)	2025-05-30	一种含哌啶环化合物的苯磺酸盐、其制备方法及应用
Clark et al.	1950	Reaction of Phenylmagnesium Bromide with Basically Substituted Nitriles
CN110128354A (zh)	2019-08-16	一种5-氟-2-甲磺酰基-4-氨基嘧啶的制备方法
JPS60246349A (ja)	1985-12-06	２−置換−１−ジメチルアミノメチル−シクロヘキサン及びその製造法
JPH0321549B2 (de)	1991-03-22
JPS63179848A (ja)	1988-07-23	光学活性な２−シクロペンテン−４−オン−１−オ−ルのエステル類の製造法
JPS60130568A (ja)	1985-07-12	７−アルキル−８−ハイドロキシキノリンの製造方法
BE477026A (de)
CN111689871A (zh)	2020-09-22	一种甲磺酸沙芬酰胺的合成制备