NO762725L - Fremgangsm}te og nye mellomprodukter for fremstilling av 6,11-dihydrodibenzo-(b.e.)-thiepin-11-one-3-eddiksyre - Google Patents

Fremgangsm}te og nye mellomprodukter for fremstilling av 6,11-dihydrodibenzo-(b.e.)-thiepin-11-one-3-eddiksyre

Info

Publication number: NO762725L
Authority: NO; Norway
Prior art keywords: thiepin; acid; stated; dihydrodibenzo; acetic acid
Prior art date: 1976-06-18

Application number

NO762725A

Other languages

English (en)

Norwegian (no)

Inventor

Jack Ackrell

Original Assignee

Syntex Inc

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.)

1976-06-18

Filing date

1976-08-05

Publication date

1977-12-20

1976-08-05 Application filed by Syntex Inc filed Critical Syntex Inc

1977-12-20 Publication of NO762725L publication Critical patent/NO762725L/no

Links

QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 title claims description 25
238000000034 method Methods 0.000 title claims description 15
239000000543 intermediate Substances 0.000 title description 4
238000002360 preparation method Methods 0.000 title description 4
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 14
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 9
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 9
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 8
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 8
239000002253 acid Substances 0.000 claims description 8
150000001875 compounds Chemical class 0.000 claims description 8
229910000147 aluminium phosphate Inorganic materials 0.000 claims description 7
239000000203 mixture Substances 0.000 claims description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
WEVYAHXRMPXWCK-UHFFFAOYSA-N acetonitrile Substances CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 6
239000002585 base Substances 0.000 claims description 6
238000006243 chemical reaction Methods 0.000 claims description 6
238000010992 reflux Methods 0.000 claims description 5
150000008044 alkali metal hydroxides Chemical class 0.000 claims description 3
239000000284 extract Substances 0.000 claims description 3
230000007062 hydrolysis Effects 0.000 claims description 3
238000006460 hydrolysis reaction Methods 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 3
239000012299 nitrogen atmosphere Substances 0.000 claims description 3
239000003960 organic solvent Substances 0.000 claims description 3
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 2
238000009835 boiling Methods 0.000 claims description 2
239000002244 precipitate Substances 0.000 claims description 2
229910052938 sodium sulfate Inorganic materials 0.000 claims description 2
235000011152 sodium sulphate Nutrition 0.000 claims description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims 2
239000005909 Kieselgur Substances 0.000 claims 1
230000002378 acidificating effect Effects 0.000 claims 1
150000007513 acids Chemical class 0.000 claims 1
239000000706 filtrate Substances 0.000 claims 1
230000003301 hydrolyzing effect Effects 0.000 claims 1
230000020477 pH reduction Effects 0.000 claims 1
229910000029 sodium carbonate Inorganic materials 0.000 claims 1
239000002904 solvent Substances 0.000 claims 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
229960000583 acetic acid Drugs 0.000 description 8
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
150000003839 salts Chemical class 0.000 description 4
-1 sodium triacetoxyaluminum hydride Chemical class 0.000 description 4
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
206010061218 Inflammation Diseases 0.000 description 3
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
230000004054 inflammatory process Effects 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
206010037660 Pyrexia Diseases 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
238000005903 acid hydrolysis reaction Methods 0.000 description 2
239000012298 atmosphere Substances 0.000 description 2
238000010945 base-catalyzed hydrolysis reactiony Methods 0.000 description 2
KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 2
210000003754 fetus Anatomy 0.000 description 2
238000002955 isolation Methods 0.000 description 2
229910052943 magnesium sulfate Inorganic materials 0.000 description 2
235000019341 magnesium sulphate Nutrition 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
230000035935 pregnancy Effects 0.000 description 2
239000000047 product Substances 0.000 description 2
229910000033 sodium borohydride Inorganic materials 0.000 description 2
239000012279 sodium borohydride Substances 0.000 description 2
238000004809 thin layer chromatography Methods 0.000 description 2
208000010392 Bone Fractures Diseases 0.000 description 1
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
241000124008 Mammalia Species 0.000 description 1
208000006670 Multiple fractures Diseases 0.000 description 1
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
208000002193 Pain Diseases 0.000 description 1
206010052428 Wound Diseases 0.000 description 1
208000027418 Wounds and injury Diseases 0.000 description 1
239000000730 antalgic agent Substances 0.000 description 1
239000002260 anti-inflammatory agent Substances 0.000 description 1
230000003110 anti-inflammatory effect Effects 0.000 description 1
230000001754 anti-pyretic effect Effects 0.000 description 1
239000003146 anticoagulant agent Substances 0.000 description 1
229940127219 anticoagulant drug Drugs 0.000 description 1
239000002221 antipyretic Substances 0.000 description 1
239000000010 aprotic solvent Substances 0.000 description 1
206010003246 arthritis Diseases 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
239000013078 crystal Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 1
238000004821 distillation Methods 0.000 description 1
239000003480 eluent Substances 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000003527 fibrinolytic agent Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
230000004968 inflammatory condition Effects 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
239000011707 mineral Substances 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
229940035363 muscle relaxants Drugs 0.000 description 1
210000002346 musculoskeletal system Anatomy 0.000 description 1
239000003158 myorelaxant agent Substances 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
238000003672 processing method Methods 0.000 description 1
238000000746 purification Methods 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000000926 separation method Methods 0.000 description 1
230000035939 shock Effects 0.000 description 1
210000002460 smooth muscle Anatomy 0.000 description 1
239000000050 smooth muscle relaxant Substances 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
FKHIFSZMMVMEQY-UHFFFAOYSA-N talc Chemical compound [Mg+2].[O-][Si]([O-])=O FKHIFSZMMVMEQY-UHFFFAOYSA-N 0.000 description 1
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 description 1
210000001519 tissue Anatomy 0.000 description 1
210000004291 uterus Anatomy 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D337/00—Heterocyclic compounds containing rings of more than six members having one sulfur atom as the only ring hetero atom
- C07D337/02—Seven-membered rings
- C07D337/06—Seven-membered rings condensed with carbocyclic rings or ring systems
- C07D337/10—Seven-membered rings condensed with carbocyclic rings or ring systems condensed with two six-membered rings
- C07D337/12—[b,e]-condensed
- 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

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Pain & Pain Management (AREA)
Rheumatology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

NO762725A 1976-06-18 1976-08-05 Fremgangsm}te og nye mellomprodukter for fremstilling av 6,11-dihydrodibenzo-(b.e.)-thiepin-11-one-3-eddiksyre NO762725L (no)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US05/697,651 US4051149A (en)	1976-06-18	1976-06-18	6,11-Dihydrodibenzo-[b.e.]-thiepin-11-one-3-acetonitrile

Publications (1)

Publication Number	Publication Date
NO762725L true NO762725L (no)	1977-12-20

Family

ID=24801960

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO762725A NO762725L (no)	1976-06-18	1976-08-05	Fremgangsm}te og nye mellomprodukter for fremstilling av 6,11-dihydrodibenzo-(b.e.)-thiepin-11-one-3-eddiksyre

Country Status (8)

Country	Link
US (1)	US4051149A (da)
JP (1)	JPS52156881A (da)
DE (1)	DE2727148A1 (da)
DK (1)	DK351376A (da)
ES (1)	ES459898A1 (da)
FI (1)	FI762237A7 (da)
NO (1)	NO762725L (da)
SE (1)	SE7608721L (da)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4536507A (en) *	1977-07-26	1985-08-20	Merck & Co., Inc.	Prostaglandin antagonists
US4130654A (en) *	1978-01-30	1978-12-19	Syntex (U.S.A.) Inc.	Novel 4-(8X-6,11-dihydrodibenzo-[b.e.]-thiepin-11-one-3-yl)-4-oxobutyric acids, methods of preparation, compositions and uses thereof

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3975437A (en) *	1973-03-02	1976-08-17	Rhone-Poulenc S.A.	Dibenzo (a,d) cycloheptene derivatives
US3979430A (en) *	1975-09-08	1976-09-07	Syntex (U.S.A.) Inc.	Solvolytic process for the preparation of 2-(5H-dibenzo[a,d]cyclohepten-5-on-2-yl)acetic, propionic and butyric acids

1976
- 1976-06-18 US US05/697,651 patent/US4051149A/en not_active Expired - Lifetime
- 1976-08-03 SE SE7608721A patent/SE7608721L/xx unknown
- 1976-08-04 FI FI762237A patent/FI762237A7/fi not_active Application Discontinuation
- 1976-08-04 DK DK351376A patent/DK351376A/da unknown
- 1976-08-05 NO NO762725A patent/NO762725L/no unknown
1977
- 1977-06-13 JP JP6976477A patent/JPS52156881A/ja active Pending
- 1977-06-16 DE DE19772727148 patent/DE2727148A1/de active Pending
- 1977-06-17 ES ES459898A patent/ES459898A1/es not_active Expired

Also Published As

Publication number	Publication date
JPS52156881A (en)	1977-12-27
SE7608721L (sv)	1977-12-19
FI762237A7 (da)	1977-12-19
ES459898A1 (es)	1978-11-16
US4051149A (en)	1977-09-27
DE2727148A1 (de)	1977-12-29
DK351376A (da)	1977-12-19

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US4228299A (en)	1980-10-14	Chemical process for preparing alkyl esters or the amide of 3-(β,.beta.
US3953490A (en)	1976-04-27	Preparation of (3-trifluoromethylphenoxy)(4-chlorophenyl)acetonitrile
US4284797A (en)	1981-08-18	Process for separating mixtures of 3- and 4-nitrophthalic acid
NO762725L (no)	1977-12-20	Fremgangsm}te og nye mellomprodukter for fremstilling av 6,11-dihydrodibenzo-(b.e.)-thiepin-11-one-3-eddiksyre
US4304930A (en)	1981-12-08	Process for the preparation of 2-(3-phenoxy-phenyl)-propionic acid
US5233082A (en)	1993-08-03	Method of making 3-hydroxy-2,4,5-trifluorobenzoic acid
KR870001315B1 (ko)	1987-07-13	2-클로로-3-트리플루오로 메틸벤즈알데하이드의 제조방법
SU502607A3 (ru)	1976-02-05	Способ получени лактамов
SU530642A3 (ru)	1976-09-30	Способ получени производных индол-2-карбоновой кислоты или их солей
US3965173A (en)	1976-06-22	Process for preparing p-(5-chloro-2-methoxy-benzamidoethyl)-benzene sulfonamide
KR890001241B1 (ko)	1989-04-28	4-아세틸 이소퀴놀리논 화합물의 제조방법
US4845279A (en)	1989-07-04	Method of preparing 4-trifluoromethyl-2-nitrobenzoic acid and novel isomer
JPS6075471A (ja)	1985-04-27	３，４−ジフエニルイソオキサゾ−ル−５−酢酸類の製造方法
JPH0522709B2 (da)	1993-03-30
JPS6344746B2 (da)	1988-09-06
US4288615A (en)	1981-09-08	Process for recovering 3-nitrobenzoic acid
FI71299C (fi)	1986-12-19	Foerening anvaendbar saosom mellanprodukt vid framstaellning av terapeutiskt vaerdefull 2-(6-metoxi-2-naftyl)-propionsyra
Frankel et al.	1958	Preparation of aliphatic secondary nitramines
NO762723L (no)	1977-12-20	Hydrolytisk fremgangsm}te for fremstilling av 6,11-dihydrodibenzo-(b.e.)-thiepin-11-one-3-eddiksyre
NO122649B (da)	1971-07-26
SU786888A3 (ru)	1980-12-07	Способ получени полизамещенных эфиров 4-алкиламинобензойной кислоты
CA1038400A (en)	1978-09-12	1-indancarboxylic acids
NO135938B (da)	1977-03-21
EP0041576B1 (en)	1985-02-13	1-(2,6-dichlorophenyl)-2-quinolinoneimine-3-carboxylic acid, production process therefor and anti-inflammatory and analgesic composition containing the compound
KR810000802B1 (ko)	1981-07-08	4-벤조일피라졸 유도체 및 그의 금속염의 제조방법