CA2097190A1 - Compositions et procedes de preparation de composes polycycliques optiquement purs renfermant de l'oxygene et presentant au moins deux centres chiraux - Google Patents

Compositions et procedes de preparation de composes polycycliques optiquement purs renfermant de l'oxygene et presentant au moins deux centres chiraux

Info

Publication number: CA2097190A1
Authority: CA; Canada
Prior art keywords: acid; hydrogen; compound; formula; halo
Prior art date: 1990-11-29
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.): Abandoned

Application number

CA 2097190

Other languages

English (en)

Inventor

John E. Airey

Frederick A. Golec

Matthew R. Powers

Walter Rodriguez

William L. Studt

Rick G. Woodward

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.)

Rhone Poulenc Rorer International Holdings Inc

Aventis Pharmaceuticals Inc

Original Assignee

Individual

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.)

1990-11-29

Filing date

1991-09-12

Publication date

1992-05-30

1991-09-12 Application filed by Individual filed Critical Individual

1992-05-30 Publication of CA2097190A1 publication Critical patent/CA2097190A1/fr

Status Abandoned legal-status Critical Current

Links

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229910052744 lithium Inorganic materials 0.000 description 1
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229940040692 lithium hydroxide monohydrate Drugs 0.000 description 1
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VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
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229940098779 methanesulfonic acid Drugs 0.000 description 1
MZTSPMMALAMSFP-UHFFFAOYSA-N methyl 4-chloro-8-oxatricyclo[7.3.1.02,7]trideca-2(7),3,5-triene-6-carboxylate Chemical compound C1C2CCCC1OC1=C2C=C(Cl)C=C1C(=O)OC MZTSPMMALAMSFP-UHFFFAOYSA-N 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
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230000000701 neuroleptic effect Effects 0.000 description 1
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230000009871 nonspecific binding Effects 0.000 description 1
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OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
239000007968 orange flavor Substances 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
210000005034 parasympathetic neuron Anatomy 0.000 description 1
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239000002245 particle Substances 0.000 description 1
239000008188 pellet Substances 0.000 description 1
208000011906 peptic ulcer disease Diseases 0.000 description 1
230000008447 perception Effects 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
229960003742 phenol Drugs 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
230000001766 physiological effect Effects 0.000 description 1
230000035790 physiological processes and functions Effects 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229920005862 polyol Polymers 0.000 description 1
150000003077 polyols Chemical class 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
230000002335 preservative effect Effects 0.000 description 1
230000002265 prevention Effects 0.000 description 1
239000002325 prokinetic agent Substances 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
238000011321 prophylaxis Methods 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
238000010791 quenching Methods 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
230000005855 radiation Effects 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
238000001959 radiotherapy Methods 0.000 description 1
239000000376 reactant Substances 0.000 description 1
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238000001525 receptor binding assay Methods 0.000 description 1
238000011084 recovery Methods 0.000 description 1
229920003987 resole Polymers 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
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
239000004208 shellac Substances 0.000 description 1
229940113147 shellac Drugs 0.000 description 1
235000013874 shellac Nutrition 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
229910052709 silver Inorganic materials 0.000 description 1
239000004332 silver Substances 0.000 description 1
210000002460 smooth muscle Anatomy 0.000 description 1
238000002791 soaking Methods 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910001415 sodium ion Inorganic materials 0.000 description 1
235000010199 sorbic acid Nutrition 0.000 description 1
239000004334 sorbic acid Substances 0.000 description 1
229940075582 sorbic acid Drugs 0.000 description 1
238000002798 spectrophotometry method Methods 0.000 description 1
DKGZKTPJOSAWFA-UHFFFAOYSA-N spiperone Chemical compound C1=CC(F)=CC=C1C(=O)CCCN1CCC2(C(NCN2C=2C=CC=CC=2)=O)CC1 DKGZKTPJOSAWFA-UHFFFAOYSA-N 0.000 description 1
210000000952 spleen Anatomy 0.000 description 1
238000013222 sprague-dawley male rat Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
230000001954 sterilising effect Effects 0.000 description 1
238000004659 sterilization and disinfection Methods 0.000 description 1
229910052682 stishovite Inorganic materials 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000000758 substrate Substances 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
150000008163 sugars Chemical class 0.000 description 1
125000004434 sulfur atom Chemical group 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
230000002889 sympathetic effect Effects 0.000 description 1
230000005062 synaptic transmission Effects 0.000 description 1
230000002194 synthesizing effect Effects 0.000 description 1
230000009885 systemic effect Effects 0.000 description 1
239000003826 tablet Substances 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
RTKIYNMVFMVABJ-UHFFFAOYSA-L thimerosal Chemical compound [Na+].CC[Hg]SC1=CC=CC=C1C([O-])=O RTKIYNMVFMVABJ-UHFFFAOYSA-L 0.000 description 1
229940033663 thimerosal Drugs 0.000 description 1
125000004001 thioalkyl group Chemical group 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
210000003437 trachea Anatomy 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
229910052905 tridymite Inorganic materials 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
ZNRGQMMCGHDTEI-ITGUQSILSA-N tropisetron Chemical compound C1=CC=C2C(C(=O)O[C@H]3C[C@H]4CC[C@@H](C3)N4C)=CNC2=C1 ZNRGQMMCGHDTEI-ITGUQSILSA-N 0.000 description 1
238000001291 vacuum drying Methods 0.000 description 1
230000002792 vascular Effects 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
235000012431 wafers Nutrition 0.000 description 1
238000005303 weighing Methods 0.000 description 1
239000009637 wintergreen oil Substances 0.000 description 1
229950004681 zacopride Drugs 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/78—Ring systems having three or more relevant rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
- C07D453/02—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Furan Compounds (AREA)
Pyrane Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

CA 2097190 1990-11-29 1991-09-12 Compositions et procedes de preparation de composes polycycliques optiquement purs renfermant de l'oxygene et presentant au moins deux centres chiraux Abandoned CA2097190A1 (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US62024090A	1990-11-29	1990-11-29
US620,240		1990-11-29

Publications (1)

Publication Number	Publication Date
CA2097190A1 true CA2097190A1 (fr)	1992-05-30

Family

ID=24485144

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA 2097190 Abandoned CA2097190A1 (fr)	1990-11-29	1991-09-12	Compositions et procedes de preparation de composes polycycliques optiquement purs renfermant de l'oxygene et presentant au moins deux centres chiraux

Country Status (5)

Country	Link
EP (1)	EP0559656A1 (fr)
JP (1)	JPH06502849A (fr)
AU (1)	AU8659391A (fr)
CA (1)	CA2097190A1 (fr)
WO (1)	WO1992009592A1 (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
ITMI20150556A1 (it)	2015-04-16	2016-10-16	Univ Bologna Alma Mater Studiorum	Dispositivo, sistema e metodo per la diagnostica strutturale in tempo reale con onde elastiche guidate

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4668690A (en) *	1985-12-30	1987-05-26	Hoechst Roussel Pharmaceuticals Inc.	1,2,3,4,4a,9b-hexahydro-4a-aminoalkyldibenzofurans useful as analgesics, anticonvulsants or antidepressants
US4924010A (en) *	1988-02-04	1990-05-08	Rorer Pharmaceutical Corporation	Benzoxepins as intermediates to 5HT3 antagonists
US4863921A (en) *	1988-04-27	1989-09-05	Rorer Pharmaceutical Corporation	Dibenzofurancarboxamides and their pharmaceutical compositions and methods

1991
- 1991-09-12 AU AU86593/91A patent/AU8659391A/en not_active Abandoned
- 1991-09-12 EP EP19910917621 patent/EP0559656A1/fr not_active Withdrawn
- 1991-09-12 JP JP3516272A patent/JPH06502849A/ja active Pending
- 1991-09-12 CA CA 2097190 patent/CA2097190A1/fr not_active Abandoned
- 1991-09-12 WO PCT/US1991/006610 patent/WO1992009592A1/fr not_active Ceased

Also Published As

Publication number	Publication date
WO1992009592A1 (fr)	1992-06-11
AU8659391A (en)	1992-06-25
EP0559656A1 (fr)	1993-09-15
JPH06502849A (ja)	1994-03-31

Publication	Publication Date	Title
EP0430190B1 (fr)	1995-07-05	Composés tricycliques
US5011846A (en)	1991-04-30	Medicament compositions derived from quinolizine and quinolizinone and methods of use thereof
WO1989010364A1 (fr)	1989-11-02	Dibenzofurancarboxamides
US4935511A (en)	1990-06-19	Benzoxazine and benzoxazepine carboxamide 5-HT3 antagonists
US5246942A (en)	1993-09-21	Pharmaceutically useful dibenzofurancarboxamides of specific stereo-configuration
US4857517A (en)	1989-08-15	Quinuclidyl benzoxepins as 5-HT3 antagonists
HU193251B (en)	1987-08-28	Process for preparing indolo/4,3-a,b/-phenanthridine derivatives and pharmaceutical compositions containing such compounds
CA2097190A1 (fr)	1992-05-30	Compositions et procedes de preparation de composes polycycliques optiquement purs renfermant de l'oxygene et presentant au moins deux centres chiraux
US4924010A (en)	1990-05-08	Benzoxepins as intermediates to 5HT3 antagonists
EP0329932B1 (fr)	1995-10-18	Utilisation des dérivés de la quinolizine et de la quinolizinone pour la manufacture des médicaments
US5086179A (en)	1992-02-04	Process for the preparation of optically pure amides
IE59757B1 (en)	1994-03-23	5-Aminoalkyl- beta -carboline derivatives, their production and their use as durgs
WO1991019719A1 (fr)	1991-12-26	Naphtoxazines substituees utiles comme dopaminergiques
US5288731A (en)	1994-02-22	2,6-methano-2H-1-benzoxocincarboxylic acids, esters and amides
EP0329903A1 (fr)	1989-08-30	Utilisation des dérivés de quinolizinone et de la quinolizine pour la manufacture des médicaments pour le traitement du glaucome
WO1991004738A1 (fr)	1991-04-18	Dibenzofurancarboxamides
AU5337790A (en)	1991-04-28	Dibenzofurancarboxamides
CA2081011A1 (fr)	1991-10-24	Carboxamides de spiro[benzofurancycloalcane] agissant comme antagonistes 5ht3
CN120757535A (zh)	2025-10-10	含氧代吡啶并氧代脂肪环结构的化合物及其医药用途
WO1992009284A1 (fr)	1992-06-11	2,6-methano-2h-1-benzoxocincarboxamides en tant qu'antagonistes de 5-ht¿3?
EP0329905A1 (fr)	1989-08-30	Utilisation des dérivés de la quinolizine et de la quinolizinone pour la manufacture des médicaments pour l'augmentation de la motilité gastrique
HU210353A9 (hu)	1995-03-28	Új triciklusos vegyületek és ezeket tartalmazó gyógyszerkészítmények Az átmeneti oltalom a(z) 1-43. és 48. igénypontokra vonatkozik.
EP0329902A1 (fr)	1989-08-30	Utilisation des dérivés de la quinolizinone et de la quinolizine pour la manufacture des médicaments pour le traitement de la psychose
DE3912535A1 (de)	1990-10-25	Indolophenanthridine, ihre herstellung und verwendung
CY1354A (en)	1987-04-24	Azatetracyclic carbonitriles

Legal Events

Date	Code	Title	Description
1995-03-12	FZDE	Dead