FI57415C - Foerfarande foer framstaellning av adeninderivat med antioedematoes och antiallergisk aktivitet - Google Patents

Foerfarande foer framstaellning av adeninderivat med antioedematoes och antiallergisk aktivitet Download PDF

Info

Publication number: FI57415C
Authority: FI; Finland
Prior art keywords: adenine; piperazino; propyl; theory; methoxyphenyl
Prior art date: 1972-09-14

Application number

FI2810/73A

Other languages

English (en)

Finnish (fi)

Other versions

FI57415B (fi

Inventor

Werner Winter

Max Thiel

Kurt Stach

Wolfgang Schaumann

Androniki Roesch

Original Assignee

Boehringer Mannheim Gmbh

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.)

1972-09-14

Filing date

1973-09-10

Publication date

1980-08-11

1973-09-10 Application filed by Boehringer Mannheim Gmbh filed Critical Boehringer Mannheim Gmbh

1980-04-30 Application granted granted Critical

1980-04-30 Publication of FI57415B publication Critical patent/FI57415B/fi

1980-08-11 Publication of FI57415C publication Critical patent/FI57415C/fi

Links

230000003266 anti-allergic effect Effects 0.000 title 1
229960000643 adenine Drugs 0.000 claims description 19
GFFGJBXGBJISGV-UHFFFAOYSA-N Adenine Chemical compound NC1=NC=NC2=C1N=CN2 GFFGJBXGBJISGV-UHFFFAOYSA-N 0.000 claims description 13
229930024421 Adenine Natural products 0.000 claims description 11
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 8
150000003839 salts Chemical class 0.000 claims description 6
238000000034 method Methods 0.000 claims description 4
238000002360 preparation method Methods 0.000 claims description 4
125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 3
239000007795 chemical reaction product Substances 0.000 claims description 3
229910052739 hydrogen Inorganic materials 0.000 claims description 3
239000001257 hydrogen Substances 0.000 claims description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 2
206010020751 Hypersensitivity Diseases 0.000 claims description 2
239000002253 acid Substances 0.000 claims description 2
229910052801 chlorine Inorganic materials 0.000 claims description 2
125000001309 chloro group Chemical group Cl* 0.000 claims description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 2
125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims 2
DYYYQLXINVUFDE-UHFFFAOYSA-N COC1=CC=C(C=C1)C1CN(CCN1)CCCCl Chemical compound COC1=CC=C(C=C1)C1CN(CCN1)CCCCl DYYYQLXINVUFDE-UHFFFAOYSA-N 0.000 claims 1
RRHSLSUQIRLNEY-UHFFFAOYSA-N ClC1=CC=C(C=C1)C1CN(CCN1)CCCCl Chemical compound ClC1=CC=C(C=C1)C1CN(CCN1)CCCCl RRHSLSUQIRLNEY-UHFFFAOYSA-N 0.000 claims 1
208000026935 allergic disease Diseases 0.000 claims 1
IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 claims 1
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
150000001875 compounds Chemical class 0.000 description 13
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 description 5
238000002347 injection Methods 0.000 description 5
239000007924 injection Substances 0.000 description 5
239000000243 solution Substances 0.000 description 5
BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 4
BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 4
239000001630 malic acid Substances 0.000 description 4
235000011090 malic acid Nutrition 0.000 description 4
QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 4
KXKPYERIGYWUNY-UHFFFAOYSA-N 9-[3-(4-phenylpiperazin-1-yl)propyl]purin-6-amine Chemical compound C1(=CC=CC=C1)N1CCN(CC1)CCCN1C2=NC=NC(=C2N=C1)N KXKPYERIGYWUNY-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
229920002307 Dextran Polymers 0.000 description 3
241001465754 Metazoa Species 0.000 description 3
229960003545 benzarone Drugs 0.000 description 3
210000000601 blood cell Anatomy 0.000 description 3
230000000694 effects Effects 0.000 description 3
-1 isopropanol Chemical compound 0.000 description 3
239000007788 liquid Substances 0.000 description 3
239000007787 solid Substances 0.000 description 3
239000000126 substance Substances 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 2
UZURTHGTBDLJNP-UHFFFAOYSA-N 9-[2-methyl-3-(4-phenylpiperazin-1-yl)propyl]purin-6-amine Chemical compound C1(=CC=CC=C1)N1CCN(CC1)CC(CN1C2=NC=NC(=C2N=C1)N)C UZURTHGTBDLJNP-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
206010030113 Oedema Diseases 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
239000000654 additive Substances 0.000 description 2
230000004856 capillary permeability Effects 0.000 description 2
239000000969 carrier Substances 0.000 description 2
235000015165 citric acid Nutrition 0.000 description 2
229960001340 histamine Drugs 0.000 description 2
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
239000000203 mixture Substances 0.000 description 2
231100000252 nontoxic Toxicity 0.000 description 2
230000003000 nontoxic effect Effects 0.000 description 2
229940076279 serotonin Drugs 0.000 description 2
239000011734 sodium Substances 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
235000019871 vegetable fat Nutrition 0.000 description 2
LNAZSHAWQACDHT-XIYTZBAFSA-N (2r,3r,4s,5r,6s)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2s,3r,4s,5r,6r)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6r)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 description 1
PBAAKGAUXSCJAY-UHFFFAOYSA-N 1-(2-chlorophenyl)-4-(3-chloropropyl)piperazine Chemical compound C1CN(CCCCl)CCN1C1=CC=CC=C1Cl PBAAKGAUXSCJAY-UHFFFAOYSA-N 0.000 description 1
GNKBYSJAQVLQMR-UHFFFAOYSA-N 1-(3-chloro-2-methylpropyl)-4-phenylpiperazine Chemical compound C1CN(CC(CCl)C)CCN1C1=CC=CC=C1 GNKBYSJAQVLQMR-UHFFFAOYSA-N 0.000 description 1
AQLHJNRNLYDLDP-UHFFFAOYSA-N 1-(3-chloropropyl)-4-phenylpiperazine Chemical compound C1CN(CCCCl)CCN1C1=CC=CC=C1 AQLHJNRNLYDLDP-UHFFFAOYSA-N 0.000 description 1
HTXWKZDRDRFVHN-UHFFFAOYSA-N 2-methyloxiran-2-ol Chemical compound CC1(O)CO1 HTXWKZDRDRFVHN-UHFFFAOYSA-N 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
229920001817 Agar Polymers 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
206010002198 Anaphylactic reaction Diseases 0.000 description 1
FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
241000206672 Gelidium Species 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
229930195725 Mannitol Natural products 0.000 description 1
229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
208000003251 Pruritus Diseases 0.000 description 1
241000700159 Rattus Species 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
235000021355 Stearic acid Nutrition 0.000 description 1
235000011054 acetic acid Nutrition 0.000 description 1
235000010419 agar Nutrition 0.000 description 1
239000012670 alkaline solution Substances 0.000 description 1
230000007815 allergy Effects 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
208000003455 anaphylaxis Diseases 0.000 description 1
239000000872 buffer Substances 0.000 description 1
239000001506 calcium phosphate Substances 0.000 description 1
229910000389 calcium phosphate Inorganic materials 0.000 description 1
235000011010 calcium phosphates Nutrition 0.000 description 1
239000002775 capsule Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
239000007979 citrate buffer Substances 0.000 description 1
239000008139 complexing agent Substances 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
235000014113 dietary fatty acids Nutrition 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
239000003814 drug Substances 0.000 description 1
230000002884 effect on inflammation Effects 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
229930195729 fatty acid Natural products 0.000 description 1
150000004665 fatty acids Chemical class 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
235000013355 food flavoring agent Nutrition 0.000 description 1
235000003599 food sweetener Nutrition 0.000 description 1
238000009472 formulation Methods 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
239000008187 granular material Substances 0.000 description 1
150000002391 heterocyclic compounds Chemical class 0.000 description 1
229920006158 high molecular weight polymer Polymers 0.000 description 1
210000003630 histaminocyte Anatomy 0.000 description 1
150000002431 hydrogen Chemical group 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
239000004310 lactic acid Substances 0.000 description 1
235000014655 lactic acid Nutrition 0.000 description 1
239000008101 lactose Substances 0.000 description 1
230000003902 lesion Effects 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
239000000594 mannitol Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
230000003472 neutralizing effect Effects 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
230000002093 peripheral effect Effects 0.000 description 1
239000000047 product Substances 0.000 description 1
150000003212 purines Chemical class 0.000 description 1
150000003230 pyrimidines Chemical class 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
LMHHRCOWPQNFTF-UHFFFAOYSA-N s-propan-2-yl azepane-1-carbothioate Chemical compound CC(C)SC(=O)N1CCCCCC1 LMHHRCOWPQNFTF-UHFFFAOYSA-N 0.000 description 1
125000005624 silicic acid group Chemical class 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
238000010998 test method Methods 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
230000002792 vascular Effects 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/26—Heterocyclic compounds containing purine ring systems with an oxygen, sulphur, or nitrogen atom directly attached in position 2 or 6, but not in both
- C07D473/32—Nitrogen atom
- C07D473/34—Nitrogen atom attached in position 6, e.g. adenine
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

FI2810/73A 1972-09-14 1973-09-10 Foerfarande foer framstaellning av adeninderivat med antioedematoes och antiallergisk aktivitet FI57415C (fi)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE2245061		1972-09-14
DE2245061A DE2245061A1 (de)	1972-09-14	1972-09-14	Derivate des adenins

Publications (2)

Publication Number	Publication Date
FI57415B FI57415B (fi)	1980-04-30
FI57415C true FI57415C (fi)	1980-08-11

Family

ID=5856300

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
FI2810/73A FI57415C (fi)	1972-09-14	1973-09-10	Foerfarande foer framstaellning av adeninderivat med antioedematoes och antiallergisk aktivitet

Country Status (15)

Country	Link
US (1)	US3917596A (es)
JP (1)	JPS5132639B2 (es)
AR (1)	AR196545A1 (es)
AT (1)	AT326143B (es)
AU (1)	AU465495B2 (es)
CA (1)	CA1001624A (es)
CH (1)	CH572483A5 (es)
DE (1)	DE2245061A1 (es)
ES (1)	ES418677A1 (es)
FI (1)	FI57415C (es)
FR (1)	FR2199978B1 (es)
GB (1)	GB1382787A (es)
NL (1)	NL153201B (es)
SE (1)	SE400767B (es)
ZA (1)	ZA737182B (es)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2401254A1 (de) *	1974-01-11	1975-11-27	Boehringer Mannheim Gmbh	Neue derivate von n hoch 6-substituierten adeninen
DE2550000A1 (de) *	1975-11-07	1977-05-12	Boehringer Mannheim Gmbh	Neue purin-derivate und verfahren zu ihrer herstellung
DE2549999A1 (de) *	1975-11-07	1977-05-12	Boehringer Mannheim Gmbh	Piperidin-derivate und verfahren zu ihrer herstellung
DE2804416A1 (de) *	1978-02-02	1979-08-09	Boehringer Mannheim Gmbh	Neue purin-derivate, verfahren zu deren herstellung sowie diese verbindungen enthaltende arzneimittel
EP1764134B1 (en) *	2001-07-30	2009-01-28	Spectrum Pharmaceuticals, Inc.	Purine derivatives linked to arylpiperazines
US11011776B2 (en)	2017-03-15	2021-05-18	Ngk Spark Plug Co., Ltd.	Lithium-ion-conductive ceramic material, lithium-ion-conductive ceramic sintered body, and lithium battery

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
BE621979R (fr) *	1962-08-31	1963-02-28	Rene A H Denayer	Procédé de préparation de dérivés de l'adénine

1972
- 1972-09-14 DE DE2245061A patent/DE2245061A1/de active Granted
1973
- 1973-09-04 US US394366A patent/US3917596A/en not_active Expired - Lifetime
- 1973-09-07 CA CA180,714A patent/CA1001624A/en not_active Expired
- 1973-09-10 ZA ZA737182A patent/ZA737182B/xx unknown
- 1973-09-10 FI FI2810/73A patent/FI57415C/fi active
- 1973-09-10 GB GB4243673A patent/GB1382787A/en not_active Expired
- 1973-09-11 ES ES418677A patent/ES418677A1/es not_active Expired
- 1973-09-11 AR AR250032A patent/AR196545A1/es active
- 1973-09-11 CH CH1298773A patent/CH572483A5/xx not_active IP Right Cessation
- 1973-09-12 FR FR7332783A patent/FR2199978B1/fr not_active Expired
- 1973-09-13 SE SE7312477A patent/SE400767B/xx unknown
- 1973-09-13 AT AT793873A patent/AT326143B/de not_active IP Right Cessation
- 1973-09-13 AU AU60309/73A patent/AU465495B2/en not_active Expired
- 1973-09-13 NL NL737312622A patent/NL153201B/xx not_active IP Right Cessation
- 1973-09-14 JP JP48104467A patent/JPS5132639B2/ja not_active Expired

Also Published As

Publication number	Publication date
SE400767B (sv)	1978-04-10
FR2199978B1 (es)	1977-01-28
CH572483A5 (es)	1976-02-13
AR196545A1 (es)	1974-02-06
AU6030973A (en)	1975-03-13
FR2199978A1 (es)	1974-04-19
US3917596A (en)	1975-11-04
ES418677A1 (es)	1976-02-16
JPS4962497A (es)	1974-06-17
DE2245061A1 (de)	1974-03-28
NL153201B (nl)	1977-05-16
FI57415B (fi)	1980-04-30
NL7312622A (es)	1974-03-18
JPS5132639B2 (es)	1976-09-14
DE2245061C2 (es)	1988-02-18
AU465495B2 (en)	1975-10-02
ZA737182B (en)	1974-09-25
AT326143B (de)	1975-11-25
GB1382787A (en)	1975-02-05
ATA793873A (de)	1975-02-15
CA1001624A (en)	1976-12-14

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FI68820B (fi)	1985-07-31	Foerfarande foer framstaellning av terapeutiskt anvaendbara amnotiazoler
US3364112A (en)	1968-01-16	Compositions and methods employing certain 6-substituted-imidazo(2, 1-b) thiazoles as anthelmintics
JP4115105B2 (ja)	2008-07-09	ピラゾール誘導体
US4400387A (en)	1983-08-23	Indolizine derivatives and uses in therapeutics
JP4188839B2 (ja)	2008-12-03	ホスファターゼインヒビーターとしてのピリミドトリアジン
PT97507B (pt)	1998-08-31	Processo para apreparacao de novos derivados de catecol farmacologicamente activos
FI57415C (fi)	1980-08-11	Foerfarande foer framstaellning av adeninderivat med antioedematoes och antiallergisk aktivitet
US3919226A (en)	1975-11-11	Certain 6-piperazinoalkylaminopurines
US4307106A (en)	1981-12-22	Aminothiazoles
US5214053A (en)	1993-05-25	Thiourea derivatives and antimicrobial agent and antiulcer agent containing the same
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US4076815A (en)	1978-02-28	Quinoxaline compound and composition, process for preparing compound, and method of combatting cholera therewith
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