DD285604A5 - Verfahren zur herstellung von enol-ethern und estern - Google Patents

Verfahren zur herstellung von enol-ethern und estern Download PDF

Info

Publication number: DD285604A5
Authority: DD; German Democratic Republic
Prior art keywords: carbon atoms; formula; alkyl; recrystallization; yield
Prior art date: 1988-10-18

Application number

DD89333653A

Other languages

German (de)

English (en)

Inventor

Thomas Ch Crawford

Lawrence A Reiter

Original Assignee

��@��Kk��

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.)

1988-10-18

Filing date

1989-10-17

Publication date

1990-12-19

1989-10-17 Application filed by ��@��Kk�� filed Critical ��@��Kk��

1990-12-19 Publication of DD285604A5 publication Critical patent/DD285604A5/de

Links

238000000034 method Methods 0.000 title claims abstract description 69
238000002360 preparation method Methods 0.000 title claims abstract description 4
150000002084 enol ethers Chemical class 0.000 title abstract description 3
-1 phenylalkanoyl Chemical group 0.000 claims abstract description 21
125000000217 alkyl group Chemical group 0.000 claims abstract description 16
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims abstract description 13
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 13
239000001257 hydrogen Substances 0.000 claims abstract description 13
125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 13
125000001589 carboacyl group Chemical group 0.000 claims abstract description 10
239000000460 chlorine Substances 0.000 claims abstract description 10
229910052801 chlorine Inorganic materials 0.000 claims abstract description 9
125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 6
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 6
239000011737 fluorine Substances 0.000 claims abstract description 6
229910052731 fluorine Inorganic materials 0.000 claims abstract description 6
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 5
125000004390 alkyl sulfonyl group Chemical group 0.000 claims abstract description 5
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract description 4
125000005194 alkoxycarbonyloxy group Chemical group 0.000 claims abstract description 4
125000004423 acyloxy group Chemical group 0.000 claims abstract description 3
125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims abstract description 3
125000006678 phenoxycarbonyl group Chemical group 0.000 claims abstract description 3
UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 claims abstract description 3
150000001875 compounds Chemical class 0.000 claims description 51
125000004432 carbon atom Chemical group C* 0.000 claims description 36
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical group ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 28
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 9
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 claims description 9
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
125000003545 alkoxy group Chemical group 0.000 claims description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 6
238000006243 chemical reaction Methods 0.000 claims description 5
239000012442 inert solvent Substances 0.000 claims description 5
239000002904 solvent Substances 0.000 claims description 4
229910000027 potassium carbonate Inorganic materials 0.000 claims description 3
235000009518 sodium iodide Nutrition 0.000 claims description 3
125000002252 acyl group Chemical class 0.000 claims description 2
150000003512 tertiary amines Chemical class 0.000 claims 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
229910000288 alkali metal carbonate Inorganic materials 0.000 claims 1
150000008041 alkali metal carbonates Chemical class 0.000 claims 1
125000004429 atom Chemical group 0.000 claims 1
229910052799 carbon Inorganic materials 0.000 claims 1
239000004744 fabric Substances 0.000 claims 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract description 13
229940002612 prodrug Drugs 0.000 abstract description 12
239000000651 prodrug Substances 0.000 abstract description 12
150000002148 esters Chemical class 0.000 abstract description 7
229940079593 drug Drugs 0.000 abstract description 3
239000003814 drug Substances 0.000 abstract description 3
239000000730 antalgic agent Substances 0.000 abstract 2
239000002243 precursor Substances 0.000 abstract 2
230000001028 anti-proliverative effect Effects 0.000 abstract 1
239000003213 antiperspirant Substances 0.000 abstract 1
125000003917 carbamoyl group Chemical class [H]N([H])C(*)=O 0.000 abstract 1
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 114
238000001953 recrystallisation Methods 0.000 description 48
238000001819 mass spectrum Methods 0.000 description 44
238000005160 1H NMR spectroscopy Methods 0.000 description 33
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 22
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 17
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
238000005481 NMR spectroscopy Methods 0.000 description 11
125000001309 chloro group Chemical group Cl* 0.000 description 9
239000000203 mixture Substances 0.000 description 8
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
238000004587 chromatography analysis Methods 0.000 description 7
238000001914 filtration Methods 0.000 description 7
239000000741 silica gel Substances 0.000 description 7
229910002027 silica gel Inorganic materials 0.000 description 7
230000003110 anti-inflammatory effect Effects 0.000 description 5
239000000047 product Substances 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
239000002253 acid Substances 0.000 description 4
150000004649 carbonic acid derivatives Chemical class 0.000 description 4
GKIRPKYJQBWNGO-OCEACIFDSA-N clomifene Chemical compound C1=CC(OCCN(CC)CC)=CC=C1C(\C=1C=CC=CC=1)=C(\Cl)C1=CC=CC=C1 GKIRPKYJQBWNGO-OCEACIFDSA-N 0.000 description 4
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 4
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical class O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
102000004005 Prostaglandin-endoperoxide synthases Human genes 0.000 description 3
108090000459 Prostaglandin-endoperoxide synthases Proteins 0.000 description 3
241000700159 Rattus Species 0.000 description 3
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
239000002168 alkylating agent Substances 0.000 description 3
229940100198 alkylating agent Drugs 0.000 description 3
239000002260 anti-inflammatory agent Substances 0.000 description 3
229940121363 anti-inflammatory agent Drugs 0.000 description 3
239000003153 chemical reaction reagent Substances 0.000 description 3
125000001153 fluoro group Chemical group F* 0.000 description 3
230000002496 gastric effect Effects 0.000 description 3
238000001727 in vivo Methods 0.000 description 3
239000007858 starting material Substances 0.000 description 3
238000012360 testing method Methods 0.000 description 3
206010053155 Epigastric discomfort Diseases 0.000 description 2
206010061218 Inflammation Diseases 0.000 description 2
108090000128 Lipoxygenases Proteins 0.000 description 2
102000003820 Lipoxygenases Human genes 0.000 description 2
241000124008 Mammalia Species 0.000 description 2
PCKPVGOLPKLUHR-UHFFFAOYSA-N OH-Indolxyl Natural products C1=CC=C2C(O)=CNC2=C1 PCKPVGOLPKLUHR-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
238000010521 absorption reaction Methods 0.000 description 2
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 2
230000000202 analgesic effect Effects 0.000 description 2
YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
238000003818 flash chromatography Methods 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
JYGFTBXVXVMTGB-UHFFFAOYSA-N indolin-2-one Chemical compound C1=CC=C2NC(=O)CC2=C1 JYGFTBXVXVMTGB-UHFFFAOYSA-N 0.000 description 2
230000004054 inflammatory process Effects 0.000 description 2
229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 2
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 2
150000003180 prostaglandins Chemical class 0.000 description 2
108090000623 proteins and genes Proteins 0.000 description 2
SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 2
238000001228 spectrum Methods 0.000 description 2
150000003871 sulfonates Chemical class 0.000 description 2
RLQZIECDMISZHS-UHFFFAOYSA-N 2-phenylcyclohexa-2,5-diene-1,4-dione Chemical compound O=C1C=CC(=O)C(C=2C=CC=CC=2)=C1 RLQZIECDMISZHS-UHFFFAOYSA-N 0.000 description 1
208000016557 Acute basophilic leukemia Diseases 0.000 description 1
206010067484 Adverse reaction Diseases 0.000 description 1
101100232409 Drosophila melanogaster icln gene Proteins 0.000 description 1
208000030453 Drug-Related Side Effects and Adverse reaction Diseases 0.000 description 1
208000009386 Experimental Arthritis Diseases 0.000 description 1
BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
206010030124 Oedema peripheral Diseases 0.000 description 1
241000283973 Oryctolagus cuniculus Species 0.000 description 1
ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
101100232415 Schizosaccharomyces pombe (strain 972 / ATCC 24843) saf5 gene Proteins 0.000 description 1
102100023152 Scinderin Human genes 0.000 description 1
101710190410 Staphylococcal complement inhibitor Proteins 0.000 description 1
230000006838 adverse reaction Effects 0.000 description 1
229940114079 arachidonic acid Drugs 0.000 description 1
235000021342 arachidonic acid Nutrition 0.000 description 1
125000003710 aryl alkyl group Chemical group 0.000 description 1
238000003556 assay Methods 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
210000004027 cell Anatomy 0.000 description 1
238000004113 cell culture Methods 0.000 description 1
239000007810 chemical reaction solvent Substances 0.000 description 1
239000013058 crude material Substances 0.000 description 1
239000012043 crude product Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 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
230000006735 deficit Effects 0.000 description 1
239000012259 ether extract Substances 0.000 description 1
238000011156 evaluation Methods 0.000 description 1
238000000605 extraction Methods 0.000 description 1
210000002950 fibroblast Anatomy 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
230000004060 metabolic process Effects 0.000 description 1
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
239000002808 molecular sieve Substances 0.000 description 1
239000000041 non-steroidal anti-inflammatory agent Substances 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
150000005623 oxindoles Chemical class 0.000 description 1
229940094443 oxytocics prostaglandins Drugs 0.000 description 1
125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
238000011160 research Methods 0.000 description 1
150000003839 salts Chemical group 0.000 description 1
229910001961 silver nitrate Inorganic materials 0.000 description 1
239000002002 slurry 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
238000003756 stirring Methods 0.000 description 1
210000002784 stomach Anatomy 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
210000002437 synoviocyte Anatomy 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
- 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]
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/32—Oxygen atoms
- C07D209/34—Oxygen atoms in position 2
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6558—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system
- C07F9/65586—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system at least one of the hetero rings does not contain nitrogen as ring hetero atom

Landscapes

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

DD89333653A 1988-10-18 1989-10-17 Verfahren zur herstellung von enol-ethern und estern DD285604A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
PCT/US1988/003658 WO1990004393A1 (fr)	1988-10-18	1988-10-18	Promedicaments de 3-acyle-2-indoxyle-1-carboxamides anti-inflammatoires

Publications (1)

Publication Number	Publication Date
DD285604A5 true DD285604A5 (de)	1990-12-19

Family

ID=22208957

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD89333653A DD285604A5 (de)	1988-10-18	1989-10-17	Verfahren zur herstellung von enol-ethern und estern

Country Status (33)

Country	Link
US (1)	US5118703A (fr)
JP (1)	JPH07597B2 (fr)
KR (1)	KR910007237B1 (fr)
CN (1)	CN1022241C (fr)
AP (1)	AP118A (fr)
AR (1)	AR246519A1 (fr)
AT (1)	ATE125794T1 (fr)
AU (1)	AU606819B2 (fr)
BG (1)	BG50834A3 (fr)
CA (1)	CA1339558C (fr)
CZ (1)	CZ278983B6 (fr)
DD (1)	DD285604A5 (fr)
DK (1)	DK514989A (fr)
EG (1)	EG19887A (fr)
FI (1)	FI95253C (fr)
HU (1)	HU208421B (fr)
IE (1)	IE66586B1 (fr)
IL (1)	IL91960A (fr)
IS (1)	IS1598B (fr)
MA (1)	MA21657A1 (fr)
MX (1)	MX18021A (fr)
MY (1)	MY104238A (fr)
NO (1)	NO178027C (fr)
NZ (1)	NZ231044A (fr)
OA (1)	OA09140A (fr)
PH (1)	PH27554A (fr)
PL (2)	PL162316B1 (fr)
PT (1)	PT92000B (fr)
RO (1)	RO109195B1 (fr)
RU (1)	RU2036905C1 (fr)
SK (1)	SK590689A3 (fr)
WO (1)	WO1990004393A1 (fr)
YU (1)	YU48070B (fr)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5059693A (en) *	1989-10-06	1991-10-22	Pfizer Inc.	Process for making 3-aroyl-2-oxindole-1-carboxamides
DE69306595T2 (de) *	1992-11-23	1997-04-03	Pfizer	Regioselektive synthese von 4-chlor-2-thiophencarbonsäure
US5270331A (en) *	1993-01-26	1993-12-14	Pfizer, Inc.	Prodrugs of antiinflammatory 3-acyl-2-oxindole-1-carboxamides
US5607959A (en) *	1993-02-09	1997-03-04	Pfizer Inc.	Oxindole 1-[N-(alkoxycarbonyl) ] carboxamides and 1-(N-carboxamido) carboxamides as antiinflammatory agents
US5449788A (en) *	1994-01-28	1995-09-12	Catalytica, Inc.	Process for preparing 2-oxindole-1-carboxamides
CN1094819C (zh) *	1997-04-30	2002-11-27	大兴株式会社	环状坯料之制造装置
EP0984012A3 (fr) *	1998-08-31	2001-01-10	Pfizer Products Inc.	Promedicaments d'oxindole liberant du monoxyde d'azote avec propriétés analgesiques et antiinflammatoires
JP2003512396A (ja) *	1999-10-26	2003-04-02	ザ・ユニバーシティ・オブ・テキサス・サウスウエスタン・メディカル・センター	インドリン化合物を投与することを含む脱毛症の処置方法

Family Cites Families (12)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
NL96047C (fr) *	1956-06-08
US3564009A (en) *	1966-01-13	1971-02-16	Sumitomo Chemical Co	Process for producing 1-acylindole derivatives
BE756447A (fr) *	1969-10-15	1971-03-22	Pfizer	Oxindolecarboxamides
US3923996A (en) *	1972-07-31	1975-12-02	Sandoz Ag	3-Substituted-oxindoles in compositions and methods of treating obesity
IE53102B1 (en) *	1981-05-12	1988-06-22	Ici Plc	Pharmaceutical spiro-succinimide derivatives
DE3268971D1 (en) *	1981-10-06	1986-03-20	Ici Plc	Biochemical process
US4556672A (en) *	1984-03-19	1985-12-03	Pfizer Inc.	3-Substituted 2-oxindole-1-carboxamides as analgesic and anti-inflammatory agents
US4752609A (en) *	1985-06-20	1988-06-21	Pfizer Inc.	Analgesic and antiinflammatory 1,3-diacyl-2-oxindole compounds
UA25898A1 (uk) *	1987-02-02	1999-02-26	Пфайзер Інк.	Спосіб одержаhhя кристалічhої hатрієвої солі 5-хлор-3-(2-теhоїл)-2-оксііhдол-1-карбоксаміду
EP0365194B1 (fr) *	1988-10-18	1995-08-02	Pfizer Inc.	Prodrogues de 3-aryl-2-oxindole-1-carboxamide antiinflammatoires
US5047554A (en) *	1989-04-18	1991-09-10	Pfizer Inc.	3-substituted-2-oxindole derivatives
US5059693A (en) *	1989-10-06	1991-10-22	Pfizer Inc.	Process for making 3-aroyl-2-oxindole-1-carboxamides

1988
- 1988-10-18 US US07/675,883 patent/US5118703A/en not_active Expired - Lifetime
- 1988-10-18 HU HU886740A patent/HU208421B/hu not_active IP Right Cessation
- 1988-10-18 RO RO147347A patent/RO109195B1/ro unknown
- 1988-10-18 SK SK5906-89A patent/SK590689A3/sk unknown
- 1988-10-18 WO PCT/US1988/003658 patent/WO1990004393A1/fr not_active Ceased
- 1988-10-18 MX MX1802188A patent/MX18021A/es unknown
1989
- 1989-09-20 IS IS3509A patent/IS1598B/is unknown
- 1989-09-28 CA CA000614317A patent/CA1339558C/fr not_active Expired - Fee Related
- 1989-10-04 PH PH39329A patent/PH27554A/en unknown
- 1989-10-09 AT AT89310319T patent/ATE125794T1/de active
- 1989-10-12 IL IL9196089A patent/IL91960A/xx not_active IP Right Cessation
- 1989-10-16 PT PT92000A patent/PT92000B/pt not_active IP Right Cessation
- 1989-10-16 YU YU200589A patent/YU48070B/sh unknown
- 1989-10-16 BG BG090022A patent/BG50834A3/xx unknown
- 1989-10-16 AP APAP/P/1989/000141A patent/AP118A/en active
- 1989-10-16 MY MYPI89001415A patent/MY104238A/en unknown
- 1989-10-17 JP JP1270174A patent/JPH07597B2/ja not_active Expired - Lifetime
- 1989-10-17 AR AR89315179A patent/AR246519A1/es active
- 1989-10-17 IE IE333289A patent/IE66586B1/en not_active IP Right Cessation
- 1989-10-17 KR KR1019890014914A patent/KR910007237B1/ko not_active Expired
- 1989-10-17 PL PL89281871A patent/PL162316B1/pl unknown
- 1989-10-17 DK DK514989A patent/DK514989A/da not_active Application Discontinuation
- 1989-10-17 MA MA21909A patent/MA21657A1/fr unknown
- 1989-10-17 PL PL89296831A patent/PL163112B1/pl unknown
- 1989-10-17 OA OA59665A patent/OA09140A/fr unknown
- 1989-10-17 CN CN89107943A patent/CN1022241C/zh not_active Expired - Fee Related
- 1989-10-17 NZ NZ231044A patent/NZ231044A/en unknown
- 1989-10-17 AU AU42956/89A patent/AU606819B2/en not_active Ceased
- 1989-10-17 DD DD89333653A patent/DD285604A5/de not_active IP Right Cessation
- 1989-10-18 EG EG49689A patent/EG19887A/xx active
- 1989-10-18 CZ CS895906A patent/CZ278983B6/cs not_active IP Right Cessation
1991
- 1991-04-17 RU SU914895525A patent/RU2036905C1/ru active
- 1991-04-17 NO NO911512A patent/NO178027C/no unknown
- 1991-04-17 FI FI911855A patent/FI95253C/fi not_active IP Right Cessation

Also Published As

Publication number	Publication date
RO109195B1 (ro)	1994-12-30
CA1339558C (fr)	1997-11-25
NO178027B (no)	1995-10-02
JPH07597B2 (ja)	1995-01-11
AP118A (en)	1991-02-22
KR900006285A (ko)	1990-05-07
IS3509A7 (is)	1990-04-19
CN1022241C (zh)	1993-09-29
PT92000A (pt)	1990-04-30
MA21657A1 (fr)	1990-07-01
NO911512D0 (no)	1991-04-17
IL91960A (en)	1994-04-12
CN1041938A (zh)	1990-05-09
IE893332L (en)	1990-04-18
PL162316B1 (pl)	1993-09-30
NZ231044A (en)	1990-12-21
AR246519A1 (es)	1994-08-31
FI911855A0 (fi)	1991-04-17
PT92000B (pt)	1995-06-30
HU886740D0 (en)	1991-07-29
WO1990004393A1 (fr)	1990-05-03
HUT58052A (en)	1992-01-28
MX18021A (es)	1993-11-01
ATE125794T1 (de)	1995-08-15
NO911512L (no)	1991-06-12
MY104238A (en)	1994-02-28
US5118703A (en)	1992-06-02
DK514989D0 (da)	1989-10-17
JPH02149559A (ja)	1990-06-08
FI95253C (fi)	1996-01-10
YU200589A (en)	1991-02-28
BG50834A3 (en)	1992-11-16
IE66586B1 (en)	1996-01-24
KR910007237B1 (ko)	1991-09-24
SK278175B6 (en)	1996-03-06
DK514989A (da)	1990-04-19
PL163112B1 (pl)	1994-02-28
AU4295689A (en)	1990-04-26
AP8900141A0 (en)	1989-10-31
IL91960A0 (en)	1990-07-12
NO178027C (no)	1996-01-10
IS1598B (is)	1996-05-20
YU48070B (sh)	1997-01-08
CZ278983B6 (en)	1994-11-16
HU208421B (en)	1993-10-28
RU2036905C1 (ru)	1995-06-09
OA09140A (fr)	1991-10-31
SK590689A3 (en)	1996-03-06
CZ590689A3 (en)	1994-04-13
PH27554A (en)	1993-08-18
AU606819B2 (en)	1991-02-14
FI95253B (fi)	1995-09-29
EG19887A (en)	1996-03-31

Legal Events

Date	Code	Title	Description
1999-07-08	ENJ	Ceased due to non-payment of renewal fee

Publication	Publication Date	Title
EP0328000A2 (fr)	1989-08-16	Dérivés d'indolocarbazole, procédé pour leur préparation et médicaments les contenant
CH646980A5 (de)	1984-12-28	Verfahren zur herstellung neuer hydroxylamin-substituierter aliphatischer phosphonsaeuren.
EP0096296A2 (fr)	1983-12-21	Dérivés de 1-sulfo-2-oxoazétidine
DD213919A5 (de)	1984-09-26	Verfahren zur herstellung von beta-lactam derivaten
EP0270982B1 (fr)	1994-04-13	Dérivés bicycliques d'acides-aminés, procédé et intermédiaires de préparation et utilisation
US4389408A (en)	1983-06-21	Novel ampicillin esters and production thereof
DE3131527A1 (de)	1983-02-24	1-phenyl-2-aminocarbonylindol-verbindungen sowie verfahren und zwischenprodukte zu ihrer herstellung und diese verbindungen enthaltende arzneimittel
EP0116360A1 (fr)	1984-08-22	Composé de 1-phényl-2-aminocarbonylindole, leur préparation et les médicaments les contenant
DE2740280A1 (de)	1978-03-09	7-acylamino-8-oxo-3-oxa-1-azabicyclo eckige klammer auf 4.2.0 eckige klammer zu octan-2-carbonsaeure-derivate
PT87660B (pt)	1992-10-30	Processo para a preparacao de derivados de labdano polioxigenados e de composicoes farmaceuticas que os contem
KR910007237B1 (ko)	1991-09-24	소염성 3-아실-2-옥신돌-1-카복사미드의 전구약제
DE68923673T2 (de)	1996-01-18	Prodrogen von antiinflammatorischen 3-Acyl-2-oxindol-1-carboxamiden.
CH622523A5 (fr)	1981-04-15
FR2496666A1 (fr)	1982-06-25	Nouveaux derives de cephalosporine et composition pharmaceutique les contenant
DE2612926A1 (de)	1977-10-06	Neue acyl-derivate der 6-(alpha- amino-phenylacetamido)-penicillansaeure
DD232045A5 (de)	1986-01-15	Verfahren zur herstellung von vorwirkstoffen entzuendungshemmender oxicame
CH619468A5 (fr)	1980-09-30
CH641448A5 (de)	1984-02-29	Verfahren zur herstellung von beta-lactamen.
EP0663395B1 (fr)	2001-05-16	Dérivés de 3-(phénylalkylaminoalkyloxy)-5-phénylpyrazole, procédé et intermédiaires pour leur préparation et leur utilisation comme agent de réduction du rythme cardiaque
CH633290A5 (en)	1982-11-30	Process for preparing derivatives of 7-oxo-1,3-diazabicyclo[3.2.0]heptane-2-carboxylic acid
DE69330430T2 (de)	2002-08-29	Penemderivate, deren herstellung und sie enthaltende pharmazeutische zusammensetzungen
DE2230456A1 (de)	1974-01-10	4-mercapto-azetidinone-(2) und verfahren zu ihrer herstellung
CH645905A5 (de)	1984-10-31	Cephalosporinderivate, verfahren fuer ihre herstellung und antibakteriell wirkende zusammensetzungen, die solche verbindungen enthalten.
DE2615621A1 (de)	1976-10-21	Beta-lactam-antibiotika und -zwischenprodukte sowie ihr herstellungsverfahren
DE2065879A1 (de)	1976-08-26	Verfahren zur herstellung von dl-6- aminoacylamidopenicillansaeuren