CS214831B2 - Method of making the trans-3-+l4-terc.butylcyclohexyl-1-1+p-2-methyl-1-+l3-methylpiperidineopropane,3,5-dimethylpiperidineopropane and 2,6-dimmorpholino+p-propane - Google Patents

Method of making the trans-3-+l4-terc.butylcyclohexyl-1-1+p-2-methyl-1-+l3-methylpiperidineopropane,3,5-dimethylpiperidineopropane and 2,6-dimmorpholino+p-propane Download PDF

Info

Publication number: CS214831B2
Authority: CS; Czechoslovakia
Prior art keywords: trans; isomer; cis; propane; methyl
Prior art date: 1979-05-25

Application number

CS803655A

Other languages

Czech (cs)

English (en)

Inventor

Walter Himmele

Wolfgang Heberle

Friedrich W Kohlmann

Walter Wesenberg

Original Assignee

Basf 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.)

1979-05-25

Filing date

1980-05-23

Publication date

1982-06-25

1980-05-23 Application filed by Basf Ag filed Critical Basf Ag

1982-06-25 Publication of CS214831B2 publication Critical patent/CS214831B2/cs

Links

239000001294 propane Substances 0.000 title claims description 15
238000004519 manufacturing process Methods 0.000 title description 4
239000000203 mixture Substances 0.000 claims abstract description 34
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ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims description 28
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 25
238000004508 fractional distillation Methods 0.000 claims description 17
-1 1,4-disubstituted phenyl Chemical class 0.000 claims description 15
238000005984 hydrogenation reaction Methods 0.000 claims description 14
150000003839 salts Chemical class 0.000 claims description 12
230000008025 crystallization Effects 0.000 claims description 11
238000002425 crystallisation Methods 0.000 claims description 10
238000000034 method Methods 0.000 claims description 10
239000002904 solvent Substances 0.000 claims description 7
238000002360 preparation method Methods 0.000 claims description 6
238000006243 chemical reaction Methods 0.000 claims description 5
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150000001875 compounds Chemical class 0.000 abstract description 19
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MYSWGUAQZAJSOK-UHFFFAOYSA-N ciprofloxacin Chemical compound C12=CC(N3CCNCC3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 MYSWGUAQZAJSOK-UHFFFAOYSA-N 0.000 description 1
239000000084 colloidal system Substances 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
229940125782 compound 2 Drugs 0.000 description 1
235000012343 cottonseed oil Nutrition 0.000 description 1
239000002385 cottonseed oil Substances 0.000 description 1
229940109275 cyclamate Drugs 0.000 description 1
150000004292 cyclic ethers Chemical class 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
HCAJEUSONLESMK-UHFFFAOYSA-N cyclohexylsulfamic acid Chemical compound OS(=O)(=O)NC1CCCCC1 HCAJEUSONLESMK-UHFFFAOYSA-N 0.000 description 1
230000003111 delayed effect Effects 0.000 description 1
230000037304 dermatophytes Effects 0.000 description 1
239000008121 dextrose Substances 0.000 description 1
150000001983 dialkylethers Chemical class 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
239000003814 drug Substances 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
229940093499 ethyl acetate Drugs 0.000 description 1
239000000945 filler Substances 0.000 description 1
235000019264 food flavour enhancer Nutrition 0.000 description 1
238000001640 fractional crystallisation Methods 0.000 description 1
244000053095 fungal pathogen Species 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
239000007903 gelatin capsule Substances 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
239000011521 glass Substances 0.000 description 1
229940074076 glycerol formal Drugs 0.000 description 1
ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
239000011874 heated mixture Substances 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 1
235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 1
239000003701 inert diluent Substances 0.000 description 1
238000006317 isomerization reaction Methods 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000008101 lactose Substances 0.000 description 1
239000006210 lotion Substances 0.000 description 1
235000009973 maize Nutrition 0.000 description 1
239000000594 mannitol Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
CQDGTJPVBWZJAZ-UHFFFAOYSA-N monoethyl carbonate Chemical compound CCOC(O)=O CQDGTJPVBWZJAZ-UHFFFAOYSA-N 0.000 description 1
150000002780 morpholines Chemical class 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
150000002814 niacins Chemical class 0.000 description 1
235000001968 nicotinic acid Nutrition 0.000 description 1
238000010899 nucleation Methods 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
239000004006 olive oil Substances 0.000 description 1
235000008390 olive oil Nutrition 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
239000006072 paste Substances 0.000 description 1
239000000312 peanut oil Substances 0.000 description 1
WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
239000006187 pill Substances 0.000 description 1
229920002647 polyamide Polymers 0.000 description 1
229920000573 polyethylene Polymers 0.000 description 1
229940068918 polyethylene glycol 400 Drugs 0.000 description 1
229920001296 polysiloxane Polymers 0.000 description 1
229920002689 polyvinyl acetate Polymers 0.000 description 1
239000011118 polyvinyl acetate Substances 0.000 description 1
229940075065 polyvinyl acetate Drugs 0.000 description 1
239000010970 precious metal Substances 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
239000003380 propellant Substances 0.000 description 1
229960004063 propylene glycol Drugs 0.000 description 1
238000000746 purification Methods 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
229940081974 saccharin Drugs 0.000 description 1
235000019204 saccharin Nutrition 0.000 description 1
239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
150000003870 salicylic acids Chemical class 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000008159 sesame oil Substances 0.000 description 1
235000011803 sesame oil Nutrition 0.000 description 1
239000004208 shellac Substances 0.000 description 1
ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
235000013874 shellac Nutrition 0.000 description 1
229940113147 shellac Drugs 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
229910052709 silver Inorganic materials 0.000 description 1
239000004332 silver Substances 0.000 description 1
235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000008107 starch Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
230000009885 systemic effect Effects 0.000 description 1
125000001302 tertiary amino group Chemical group 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
229940116362 tragacanth Drugs 0.000 description 1
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical group COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 1
FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 1
235000012141 vanillin Nutrition 0.000 description 1
235000019871 vegetable fat Nutrition 0.000 description 1
239000001993 wax Substances 0.000 description 1
238000009736 wetting Methods 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1
239000011787 zinc oxide Substances 0.000 description 1

Classifications

- 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
- C07D295/03—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 acyclic carbon atoms
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/10—Antimycotics

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Communicable Diseases (AREA)
Animal Behavior & Ethology (AREA)
Oncology (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Hydrogenated Pyridines (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

CS803655A 1979-05-25 1980-05-23 Method of making the trans-3-+l4-terc.butylcyclohexyl-1-1+p-2-methyl-1-+l3-methylpiperidineopropane,3,5-dimethylpiperidineopropane and 2,6-dimmorpholino+p-propane CS214831B2 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19792921221 DE2921221A1 (de)	1979-05-25	1979-05-25	Trans-3-(4'-tert.-butyl-cyclohexyl-1')- 2-methyl-1-(3'-methylpiperidino, 3', 5'- dimethylpiperidino und 2', 6'-dimethylmorpholino)-propan, verfahren zu ihrer reinherstellung und diese enthaltende antimykotische mittel

Publications (1)

Publication Number	Publication Date
CS214831B2 true CS214831B2 (en)	1982-06-25

Family

ID=6071686

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS803655A CS214831B2 (en)	1979-05-25	1980-05-23	Method of making the trans-3-+l4-terc.butylcyclohexyl-1-1+p-2-methyl-1-+l3-methylpiperidineopropane,3,5-dimethylpiperidineopropane and 2,6-dimmorpholino+p-propane

Country Status (14)

Country	Link
EP (1)	EP0019764A1 (no)
JP (1)	JPS55157567A (no)
AU (1)	AU5871080A (no)
CA (1)	CA1146551A (no)
CS (1)	CS214831B2 (no)
DD (1)	DD150893A5 (no)
DE (1)	DE2921221A1 (no)
DK (1)	DK226080A (no)
ES (1)	ES491793A0 (no)
FI (1)	FI801364A7 (no)
HU (1)	HU179864B (no)
IL (1)	IL59956A0 (no)
NO (1)	NO801556L (no)
ZA (1)	ZA803108B (no)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3001581A1 (de) *	1980-01-17	1981-07-23	Basf Ag, 6700 Ludwigshafen	Substituierte n- (3(4'-tert-butyl-cyclohex-1'-en1'yl)-2-methyl-propyl-1) -cycloalkalamine, ihre herstellung und ihre anwendung als fungizide
DE3225879A1 (de) *	1982-07-10	1984-01-12	Basf Ag, 6700 Ludwigshafen	Trans-3-(4'-tert.-butylcyclohexyl-1')-2-methyl-1-dialkyl-aminopropane, ihre herstellung und verwendung als arzneimittel
DE3321712A1 (de) *	1983-06-16	1984-12-20	Basf Ag, 6700 Ludwigshafen	2,6-trans-dimethylmorpholinderivate und diese enthaltende fungizide und verfahren zur bekaempfung von pilzen
JP6105587B2 (ja)	2011-08-29	2017-04-05	セラロック、イノベーション、アクチボラグ	フロアパネル用機械式係止システム

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
BE614214A (no) *	1961-02-22
DE1214471B (de) *	1965-01-16	1966-04-14	Basf Ag	Fungizid fuer den Pflanzenschutz
AT354187B (de) *	1976-11-22	1979-12-27	Hoffmann La Roche	Fungizides mittel
DE2657476A1 (de) *	1976-12-18	1978-06-22	Basf Ag	Morpholinderivate
DE2830127A1 (de) *	1978-07-08	1980-01-17	Basf Ag	N-arylpropyl-substituierte cyclische amine
ATE3111T1 (de) *	1978-08-08	1983-05-15	F. Hoffmann-La Roche & Co. Aktiengesellschaft	Verfahren zur herstellung von phenyl-propylmorpholin- und -piperidin-derivaten.

1979
- 1979-05-25 DE DE19792921221 patent/DE2921221A1/de not_active Withdrawn
1980
- 1980-04-28 FI FI801364A patent/FI801364A7/fi not_active Application Discontinuation
- 1980-04-30 IL IL59956A patent/IL59956A0/xx unknown
- 1980-05-05 CA CA000351285A patent/CA1146551A/en not_active Expired
- 1980-05-08 EP EP80102509A patent/EP0019764A1/de not_active Withdrawn
- 1980-05-22 JP JP6721680A patent/JPS55157567A/ja active Pending
- 1980-05-22 DD DD80221320A patent/DD150893A5/de unknown
- 1980-05-23 ES ES491793A patent/ES491793A0/es active Granted
- 1980-05-23 HU HU80801307A patent/HU179864B/hu unknown
- 1980-05-23 AU AU58710/80A patent/AU5871080A/en not_active Abandoned
- 1980-05-23 NO NO801556A patent/NO801556L/no unknown
- 1980-05-23 DK DK226080A patent/DK226080A/da unknown
- 1980-05-23 ZA ZA00803108A patent/ZA803108B/xx unknown
- 1980-05-23 CS CS803655A patent/CS214831B2/cs unknown

Also Published As

Publication number	Publication date
HU179864B (en)	1982-12-28
CA1146551A (en)	1983-05-17
IL59956A0 (en)	1980-06-30
JPS55157567A (en)	1980-12-08
DE2921221A1 (de)	1980-12-11
EP0019764A1 (de)	1980-12-10
ES8102095A1 (es)	1980-12-16
NO801556L (no)	1980-11-26
ZA803108B (en)	1981-06-24
FI801364A7 (fi)	1980-11-26
ES491793A0 (es)	1980-12-16
DD150893A5 (de)	1981-09-23
DK226080A (da)	1980-11-26
AU5871080A (en)	1980-11-27

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