DD142339A5 - Verfahren zur herstellung von benzocycloheptapyranen - Google Patents

Verfahren zur herstellung von benzocycloheptapyranen Download PDF

Info

Publication number: DD142339A5
Authority: DD; German Democratic Republic
Prior art keywords: formula; hydrogen; compound; cyclohepta; pyran
Prior art date: 1978-03-09

Application number

DD79211502A

Other languages

German (de)

English (en)

Inventor

Robert A Archer

Moses W Mcmillan

Original Assignee

Lilly Co Eli

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.)

1978-03-09

Filing date

1979-03-09

Publication date

1980-06-18

1979-03-09 Application filed by Lilly Co Eli filed Critical Lilly Co Eli

1980-06-18 Publication of DD142339A5 publication Critical patent/DD142339A5/de

Links

238000000034 method Methods 0.000 title claims description 15
238000002360 preparation method Methods 0.000 title claims description 15
-1 1,1-dimethylheptyl Chemical group 0.000 claims description 97
MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 claims description 79
150000001875 compounds Chemical class 0.000 claims description 78
229910052739 hydrogen Inorganic materials 0.000 claims description 58
239000001257 hydrogen Substances 0.000 claims description 58
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 57
125000004432 carbon atom Chemical group C* 0.000 claims description 29
125000000217 alkyl group Chemical group 0.000 claims description 27
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 19
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 15
150000004880 oxines Chemical class 0.000 claims description 10
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 10
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 8
WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 claims description 8
125000003342 alkenyl group Chemical group 0.000 claims description 7
239000002253 acid Substances 0.000 claims description 6
239000003638 chemical reducing agent Substances 0.000 claims description 6
125000002252 acyl group Chemical group 0.000 claims description 5
230000007062 hydrolysis Effects 0.000 claims description 5
238000006460 hydrolysis reaction Methods 0.000 claims description 5
229910015900 BF3 Inorganic materials 0.000 claims description 4
239000012024 dehydrating agents‎ Substances 0.000 claims description 4
125000005907 alkyl ester group Chemical group 0.000 claims description 3
BXEFQPCKQSTMKA-UHFFFAOYSA-N OC(=O)C=[N+]=[N-] Chemical compound OC(=O)C=[N+]=[N-] BXEFQPCKQSTMKA-UHFFFAOYSA-N 0.000 claims description 2
230000003197 catalytic effect Effects 0.000 claims description 2
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims 1
241001122767 Theaceae Species 0.000 claims 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 52
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UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
150000002431 hydrogen Chemical group 0.000 description 8
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HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 6
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YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
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HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
239000004480 active ingredient Substances 0.000 description 4
239000000543 intermediate Substances 0.000 description 4
230000036407 pain Effects 0.000 description 4
229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
235000017557 sodium bicarbonate Nutrition 0.000 description 4
UUNIOFWUJYBVGQ-UHFFFAOYSA-N 2-amino-4-(3,4-dimethoxyphenyl)-10-fluoro-4,5,6,7-tetrahydrobenzo[1,2]cyclohepta[6,7-d]pyran-3-carbonitrile Chemical compound C1=C(OC)C(OC)=CC=C1C1C(C#N)=C(N)OC2=C1CCCC1=CC=C(F)C=C12 UUNIOFWUJYBVGQ-UHFFFAOYSA-N 0.000 description 3
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230000004071 biological effect Effects 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
238000009835 boiling Methods 0.000 description 3
238000013375 chromatographic separation Methods 0.000 description 3
239000000470 constituent Substances 0.000 description 3
WJYQYQOPIPPDLY-UHFFFAOYSA-N cyclohepta[f]chromene Chemical compound C1=CC=CC=C2C3=CC=COC3=CC=C21 WJYQYQOPIPPDLY-UHFFFAOYSA-N 0.000 description 3
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
239000003085 diluting agent Substances 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
239000000284 extract Substances 0.000 description 3
238000001990 intravenous administration Methods 0.000 description 3
150000002576 ketones Chemical class 0.000 description 3
NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 description 3
239000000825 pharmaceutical preparation Substances 0.000 description 3
230000000144 pharmacologic effect Effects 0.000 description 3
238000006722 reduction reaction Methods 0.000 description 3
239000012279 sodium borohydride Substances 0.000 description 3
229910000033 sodium borohydride Inorganic materials 0.000 description 3
239000007858 starting material Substances 0.000 description 3
238000003786 synthesis reaction Methods 0.000 description 3
238000005406 washing Methods 0.000 description 3
125000006040 2-hexenyl group Chemical group 0.000 description 2
ICGLPKIVTVWCFT-UHFFFAOYSA-N 4-methylbenzenesulfonohydrazide Chemical compound CC1=CC=C(S(=O)(=O)NN)C=C1 ICGLPKIVTVWCFT-UHFFFAOYSA-N 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
239000007818 Grignard reagent Substances 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
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DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
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125000004429 atom Chemical group 0.000 description 2
125000005605 benzo group Chemical group 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
239000002775 capsule Substances 0.000 description 2
239000000969 carrier Substances 0.000 description 2
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238000006297 dehydration reaction Methods 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
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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
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BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
230000003389 potentiating effect Effects 0.000 description 2
125000004309 pyranyl group Chemical class O1C(C=CC=C1)* 0.000 description 2
238000011160 research Methods 0.000 description 2
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SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
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OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
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CDSGJHCARATGKG-UHFFFAOYSA-N bis(3-methylbutyl)borane Chemical compound CC(C)CCBCCC(C)C CDSGJHCARATGKG-UHFFFAOYSA-N 0.000 description 1
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HABFSQRCYMSWJV-UHFFFAOYSA-N cyclohepta[f]chromen-10-ol Chemical class C12=CC(O)=CC=CC2=CC=C2C1=CC=CO2 HABFSQRCYMSWJV-UHFFFAOYSA-N 0.000 description 1
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229910052987 metal hydride Inorganic materials 0.000 description 1
150000004681 metal hydrides Chemical class 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
VNXBKJFUJUWOCW-UHFFFAOYSA-N methylcyclopropane Chemical compound CC1CC1 VNXBKJFUJUWOCW-UHFFFAOYSA-N 0.000 description 1
239000008108 microcrystalline cellulose Substances 0.000 description 1
235000019813 microcrystalline cellulose Nutrition 0.000 description 1
229940016286 microcrystalline cellulose Drugs 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
239000002808 molecular sieve Substances 0.000 description 1
125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
150000002902 organometallic compounds Chemical class 0.000 description 1
ATYBXHSAIOKLMG-UHFFFAOYSA-N oxepin Chemical compound O1C=CC=CC=C1 ATYBXHSAIOKLMG-UHFFFAOYSA-N 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
239000006187 pill Substances 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
239000004300 potassium benzoate Substances 0.000 description 1
235000010235 potassium benzoate Nutrition 0.000 description 1
229940103091 potassium benzoate Drugs 0.000 description 1
229920001592 potato starch Polymers 0.000 description 1
239000000843 powder Substances 0.000 description 1
238000011321 prophylaxis Methods 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
238000000746 purification Methods 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 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
239000000376 reactant Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000006049 ring expansion reaction Methods 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
238000012289 standard assay Methods 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
238000012360 testing method Methods 0.000 description 1
238000005303 weighing Methods 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- 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
- C07D311/94—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 condensed with rings other than six-membered or with ring systems containing such rings
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/22—Anxiolytics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A61P27/06—Antiglaucoma agents or miotics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]

Landscapes

Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
General Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Life Sciences & Earth Sciences (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Veterinary Medicine (AREA)
Pharmacology & Pharmacy (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Neurosurgery (AREA)
Biomedical Technology (AREA)
Pain & Pain Management (AREA)
Ophthalmology & Optometry (AREA)
Neurology (AREA)
Psychiatry (AREA)
Rheumatology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pyrane Compounds (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Plural Heterocyclic Compounds (AREA)

DD79211502A 1978-03-09 1979-03-09 Verfahren zur herstellung von benzocycloheptapyranen DD142339A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US05/884,883 US4152451A (en)	1978-03-09	1978-03-09	Benzocycloheptapyrans, compositions, and method of treatment

Publications (1)

Publication Number	Publication Date
DD142339A5 true DD142339A5 (de)	1980-06-18

Family

ID=25385629

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD79211502A DD142339A5 (de)	1978-03-09	1979-03-09	Verfahren zur herstellung von benzocycloheptapyranen

Country Status (29)

Country	Link
US (1)	US4152451A (da)
EP (1)	EP0004172B1 (da)
JP (1)	JPS54125675A (da)
AR (1)	AR223666A1 (da)
AT (1)	AT362791B (da)
AU (1)	AU522313B2 (da)
BG (1)	BG33285A3 (da)
CA (1)	CA1122992A (da)
CH (1)	CH638801A5 (da)
CS (1)	CS204049B2 (da)
DD (1)	DD142339A5 (da)
DE (1)	DE2962416D1 (da)
DK (1)	DK96479A (da)
EG (1)	EG13883A (da)
ES (3)	ES478415A1 (da)
FI (1)	FI790711A7 (da)
FR (1)	FR2419290A1 (da)
GB (1)	GB2017089B (da)
GR (1)	GR72750B (da)
HU (1)	HU179971B (da)
IE (1)	IE47870B1 (da)
IL (1)	IL56736A (da)
NZ (1)	NZ189781A (da)
PH (2)	PH14643A (da)
PL (5)	PL120418B1 (da)
PT (1)	PT69287A (da)
RO (5)	RO76885A (da)
SU (1)	SU824894A3 (da)
ZA (1)	ZA791108B (da)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4442089A (en) *	1982-07-06	1984-04-10	E. R. Squibb & Sons, Inc.	Method for treating glaucoma with topical or systemic ACE inhibitor compositions

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CA994791A (en) *	1971-05-12	1976-08-10	Louis S. Harris	Esters of benzopyrans
US3941782A (en) *	1972-04-27	1976-03-02	Sharps Associates	Heterocyclic esters of benzopyrans
US4025630A (en) *	1973-09-19	1977-05-24	Abbott Laboratories	Anesthesia methods using benzopyrans and esters thereof as pre-anesthesia medication
US4051152A (en) *	1976-01-07	1977-09-27	Sharps Associates	Oxo C-ring benzopyrans

1978
- 1978-03-09 US US05/884,883 patent/US4152451A/en not_active Expired - Lifetime
1979
- 1979-02-26 IL IL56736A patent/IL56736A/xx unknown
- 1979-02-26 PH PH22237A patent/PH14643A/en unknown
- 1979-02-26 PT PT69287A patent/PT69287A/pt unknown
- 1979-02-27 NZ NZ189781A patent/NZ189781A/xx unknown
- 1979-03-02 FI FI790711A patent/FI790711A7/fi not_active Application Discontinuation
- 1979-03-06 GB GB7907825A patent/GB2017089B/en not_active Expired
- 1979-03-06 DE DE7979300331T patent/DE2962416D1/de not_active Expired
- 1979-03-06 EP EP79300331A patent/EP0004172B1/en not_active Expired
- 1979-03-07 EG EG146/79A patent/EG13883A/xx active
- 1979-03-07 SU SU792738052A patent/SU824894A3/ru active
- 1979-03-07 BG BG042776A patent/BG33285A3/xx unknown
- 1979-03-07 CS CS791535A patent/CS204049B2/cs unknown
- 1979-03-07 GR GR58537A patent/GR72750B/el unknown
- 1979-03-08 RO RO7996823A patent/RO76885A/ro unknown
- 1979-03-08 CA CA323,130A patent/CA1122992A/en not_active Expired
- 1979-03-08 AT AT0175279A patent/AT362791B/de not_active IP Right Cessation
- 1979-03-08 RO RO79104792A patent/RO82378A/ro unknown
- 1979-03-08 RO RO79104793A patent/RO82379A/ro unknown
- 1979-03-08 DK DK96479A patent/DK96479A/da unknown
- 1979-03-08 AU AU44935/79A patent/AU522313B2/en not_active Ceased
- 1979-03-08 RO RO79104794A patent/RO82380A/ro unknown
- 1979-03-08 HU HU79EI844A patent/HU179971B/hu unknown
- 1979-03-08 RO RO79104791A patent/RO82377A/ro unknown
- 1979-03-08 ES ES478415A patent/ES478415A1/es not_active Expired
- 1979-03-08 CH CH225279A patent/CH638801A5/fr not_active IP Right Cessation
- 1979-03-09 ZA ZA791108A patent/ZA791108B/xx unknown
- 1979-03-09 PL PL1979227681A patent/PL120418B1/pl unknown
- 1979-03-09 PL PL1979214011A patent/PL117710B1/pl unknown
- 1979-03-09 JP JP2818579A patent/JPS54125675A/ja active Pending
- 1979-03-09 PL PL1979227678A patent/PL120365B1/pl unknown
- 1979-03-09 PL PL1979227680A patent/PL120416B1/pl unknown
- 1979-03-09 FR FR7906164A patent/FR2419290A1/fr active Granted
- 1979-03-09 DD DD79211502A patent/DD142339A5/de not_active IP Right Cessation
- 1979-03-09 PL PL1979227679A patent/PL120366B1/pl unknown
- 1979-03-10 AR AR275668A patent/AR223666A1/es active
- 1979-08-01 ES ES483053A patent/ES483053A1/es not_active Expired
- 1979-08-01 ES ES483052A patent/ES8100288A1/es not_active Expired
- 1979-08-08 IE IE712/79A patent/IE47870B1/en unknown
- 1979-12-14 PH PH23421A patent/PH16051A/en unknown

Also Published As

Publication number	Publication date
CA1122992A (en)	1982-05-04
RO82377A (ro)	1983-08-03
PL117710B1 (en)	1981-08-31
PL214011A1 (da)	1980-02-25
HU179971B (en)	1983-01-28
DE2962416D1 (en)	1982-05-19
EP0004172B1 (en)	1982-04-07
AU4493579A (en)	1979-09-13
CS204049B2 (en)	1981-03-31
RO82380A (ro)	1983-08-03
ES483052A0 (es)	1980-11-01
SU824894A3 (ru)	1981-04-23
US4152451A (en)	1979-05-01
RO82377B (ro)	1983-07-30
PH16051A (en)	1983-06-02
FR2419290B1 (da)	1981-05-29
NZ189781A (en)	1980-10-24
GB2017089B (en)	1982-09-22
IL56736A (en)	1982-08-31
GR72750B (da)	1983-12-02
ZA791108B (en)	1980-10-29
IL56736A0 (en)	1979-05-31
AT362791B (de)	1981-06-10
ES483053A1 (es)	1980-10-01
DK96479A (da)	1979-09-10
RO82379B (ro)	1983-07-30
CH638801A5 (fr)	1983-10-14
PH14643A (en)	1981-10-12
EP0004172A1 (en)	1979-09-19
AU522313B2 (en)	1982-05-27
BG33285A3 (bg)	1983-01-14
RO82379A (ro)	1983-08-03
ES478415A1 (es)	1980-01-16
PL120366B1 (en)	1982-02-27
GB2017089A (en)	1979-10-03
FI790711A7 (fi)	1979-09-10
ATA175279A (de)	1980-11-15
AR223666A1 (es)	1981-09-15
RO82378A (ro)	1983-08-03
RO82378B (ro)	1983-07-30
PL120418B1 (en)	1982-02-27
IE790712L (en)	1979-09-09
IE47870B1 (en)	1984-07-11
FR2419290A1 (fr)	1979-10-05
ES8100288A1 (es)	1980-11-01
PL120416B1 (en)	1982-02-27
PL120365B1 (en)	1982-02-27
RO82380B (ro)	1983-07-30
RO76885A (ro)	1982-02-26
EG13883A (en)	1982-12-31
PT69287A (en)	1979-03-01
JPS54125675A (en)	1979-09-29

Legal Events

Date	Code	Title	Description
1996-05-23	ENJ	Ceased due to non-payment of renewal fee

Publication	Publication Date	Title
DE2729818C2 (de)	1982-08-05	Verfahren zur Herstellung von 6a, 10a-trans-1-Hydroxy-3-alkylsubstituierten-6,6-dimethyl-6,6a,7,8,10,10a-hexahydro-9H-dibenzo[b,d]-pyran-9-onen
DE2760006C2 (de)	1985-07-04	Optisch aktive Norpinanone und Verfahren zu ihrer Herstellung
DD143612A5 (de)	1980-09-03	Verfahren zur herstellung von tetrahydrobenzoxocinen und cis-hexahydrodibenzopyranonen
EP0496238A1 (de)	1992-07-29	Substituierte Benzoxazepine und Benzthiazepine, Verfahren zu ihrer Herstellung und ihre Verwendung in Arzneimitteln
HU190500B (en)	1986-09-29	Process for the resoluvation of alcohols, phenoles and lactones
DE2729845C2 (de)	1982-06-09	Verfahren zur Herstellung von 6a, 10a-trans-1-Hydroxy-3-alkylsubstituierten-6,6-dimethyl-6,6a,7,8,10,10a-hexahydro-9H-dibenzo[b,d]pyran-9-onen
DE68902946T2 (de)	1993-04-29	Heteroarotinoid-derivate, verfahren zu deren herstellung und diese enthaltende pharmazeutische zusammenstellungen.
EP0789694B1 (de)	2003-04-09	Verfahren zur herstellung von 8-alpha,12-oxido-13,14,15,16-tetranorlabdan
DE60203937T2 (de)	2006-05-11	Herstellung von trans-kondensierte 3,3a,8,12b-tetrahydro-2h-dibenzo[3,4:6,7]cyclohepta[1,2-b]furan derivaten
CH633790A5 (de)	1982-12-31	Verfahren zur herstellung von 2-oxy-5-isopropyliden-7-hydroxy-9-substituierten-2,6-methano-3,4,5,6-tetrahydro-2h-1-benzoxocinen.
DE2016721A1 (da)	1970-10-29
DD219765A5 (de)	1985-03-13	Verfahren zur herstellung von substituierten hexahydropyrrolo (-1,2-a)-chinolin-, hexahydro-1h-pyrido (1,2-a)chinolin-, hexahydrobenzo(e)inden- und octahydrophenanthren-zns-mitteln
DD142339A5 (de)	1980-06-18	Verfahren zur herstellung von benzocycloheptapyranen
DE68905361T2 (de)	1993-09-30	Trienische Derivate mit chromenischer Struktur, Verfahren zu deren Herstellung und diese enthaltende pharmazeutische Zusammenstellungen.
DE2729844C2 (de)	1984-06-07	Verfahren zur stereoselektiven Herstellung von optisch aktiven 6a,10a-trans-1- Hydroxy-3-alkyl-6,6-dimethyl-6,6a,7,8,10,10a-hexahydro-9H-dibenzo [b,d] pyran-9-onen
DD251289A5 (de)	1987-11-11	Verfahren zur herstellung einer neuartigen racemischen oder optisch aktiven verbindung
AT366040B (de)	1982-03-10	Verfahren zur herstellung von neuen dibenzo(b,d) pyranen und deren isomeren
DE2333262A1 (de)	1974-01-24	Verfahren zur herstellung von neuen 1,1a,6,10b-tetrahydro-1,6-methano-dibenzo eckige klammer auf a,e eckige klammer zu -cyclopropa eckige klammer auf c eckige klammer zu cyclohepten-derivaten
DE3014685A1 (de)	1980-11-06	Polycyclische verbindungen und verfahren zu deren herstellung
DD219772A5 (de)	1985-03-13	Verfahren zur herstellung von spiro-hydantoin-derivaten
DE2729846A1 (de)	1978-01-19	Verfahren zur herstellung von in 3-stellung substituierten cis-1-hydroxy- 6,6-dimethyl-6,6a,7,8,10,10a-hexahydro- 9h-dibenzo eckige klammer auf b,d eckige klammer zu pyran-9-onen
US4195024A (en)	1980-03-25	Benzocycloheptapyrans, compositions, and method of treatment
KR830000796B1 (ko)	1983-04-15	벤조 사이클로헵타피란의 제조 방법
DE1443123C (de)	1971-08-26	Verfahren zur Herstellung von 13 Alkyl gona 1,3,5(10) tnenen
KR820000784B1 (ko)	1982-05-10	헥사하이드로-디벤조피라논 화합물의 광학적 이성체의 제조방법