CA1075703A - Preparation de derives des acides amidinosulfiniques - Google Patents

Preparation de derives des acides amidinosulfiniques

Info

Publication number: CA1075703A
Authority: CA; Canada
Prior art keywords: methyl; thiourea; histamine; ethyl; formula
Prior art date: 1976-03-11
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

CA320,456A

Other languages

English (en)

Inventor

Rodney C. Young

Charon R. Ganellin

Graham J. Durant

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Smith Kline and French Laboratories Ltd

Original Assignee

Smith Kline and French Laboratories Ltd

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.)

1976-03-11

Filing date

1979-01-30

Publication date

1980-04-15

1976-03-11 Priority claimed from GB9750/76A external-priority patent/GB1574214A/en

1979-01-30 Application filed by Smith Kline and French Laboratories Ltd filed Critical Smith Kline and French Laboratories Ltd

1979-01-30 Priority to CA320,456A priority Critical patent/CA1075703A/fr

1980-04-15 Application granted granted Critical

1980-04-15 Publication of CA1075703A publication Critical patent/CA1075703A/fr

Status Expired legal-status Critical Current

Links

238000004519 manufacturing process Methods 0.000 title claims description 9
FYOWZTWVYZOZSI-UHFFFAOYSA-N thiourea dioxide Chemical class NC(=N)S(O)=O FYOWZTWVYZOZSI-UHFFFAOYSA-N 0.000 title description 6
150000001875 compounds Chemical class 0.000 claims abstract description 27
125000000217 alkyl group Chemical group 0.000 claims abstract description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 4
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 8
238000000034 method Methods 0.000 claims description 7
239000000126 substance Substances 0.000 claims description 3
FPBPLBWLMYGIQR-UHFFFAOYSA-N Metiamide Chemical compound CNC(=S)NCCSCC=1N=CNC=1C FPBPLBWLMYGIQR-UHFFFAOYSA-N 0.000 claims description 2
HBPSYKUUBQFJEO-UHFFFAOYSA-N [2-[(5-methyl-1h-imidazol-4-yl)methylsulfanyl]ethylamino]-methyliminomethanesulfinic acid Chemical compound CNC(S(O)=O)=NCCSCC=1N=CNC=1C HBPSYKUUBQFJEO-UHFFFAOYSA-N 0.000 claims 2
230000000694 effects Effects 0.000 abstract description 6
229940122957 Histamine H2 receptor antagonist Drugs 0.000 abstract description 5
239000003485 histamine H2 receptor antagonist Substances 0.000 abstract description 5
210000004211 gastric acid Anatomy 0.000 abstract description 3
230000028327 secretion Effects 0.000 abstract description 3
229910052739 hydrogen Inorganic materials 0.000 abstract 1
239000001257 hydrogen Substances 0.000 abstract 1
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 51
NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 40
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 21
229960001340 histamine Drugs 0.000 description 20
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 12
102000003710 Histamine H2 Receptors Human genes 0.000 description 7
108090000050 Histamine H2 Receptors Proteins 0.000 description 7
150000003839 salts Chemical class 0.000 description 7
230000031018 biological processes and functions Effects 0.000 description 6
239000002253 acid Substances 0.000 description 5
239000007787 solid Substances 0.000 description 5
150000003585 thioureas Chemical class 0.000 description 5
HXRBAVXGYZUSED-UHFFFAOYSA-N Burimamide Chemical compound CNC(=S)NCCCCC1=CN=CN1 HXRBAVXGYZUSED-UHFFFAOYSA-N 0.000 description 4
239000004480 active ingredient Substances 0.000 description 4
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
239000007788 liquid Substances 0.000 description 4
239000000203 mixture Substances 0.000 description 4
229940044551 receptor antagonist Drugs 0.000 description 4
239000002464 receptor antagonist Substances 0.000 description 4
BLBKIPKKNZTVOL-UHFFFAOYSA-N 1-[2-[(5-amino-1,3,4-thiadiazol-2-yl)methylsulfanyl]ethyl]-3-methylthiourea Chemical compound CNC(=S)NCCSCC1=NN=C(N)S1 BLBKIPKKNZTVOL-UHFFFAOYSA-N 0.000 description 3
UKUMBWIAJWVEDN-UHFFFAOYSA-N 4-Methylburimamide Chemical compound CNC(=S)NCCCCC=1N=CNC=1C UKUMBWIAJWVEDN-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
241000700159 Rattus Species 0.000 description 3
230000036772 blood pressure Effects 0.000 description 3
239000003937 drug carrier Substances 0.000 description 3
230000027119 gastric acid secretion Effects 0.000 description 3
230000001404 mediated effect Effects 0.000 description 3
229960000582 mepyramine Drugs 0.000 description 3
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 3
230000007935 neutral effect Effects 0.000 description 3
239000008194 pharmaceutical composition Substances 0.000 description 3
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
238000006467 substitution reaction Methods 0.000 description 3
FHMWSAPSSOSBSQ-UHFFFAOYSA-N 1-[2-[(4-bromo-1,2-thiazol-3-yl)methylsulfanyl]ethyl]-3-methylthiourea Chemical compound CNC(=S)NCCSCC1=NSC=C1Br FHMWSAPSSOSBSQ-UHFFFAOYSA-N 0.000 description 2
CNEJJRSFRXETDG-UHFFFAOYSA-N 1-[3-(1h-imidazol-2-ylsulfanyl)propyl]-3-methylthiourea Chemical compound CNC(=S)NCCCSC1=NC=CN1 CNEJJRSFRXETDG-UHFFFAOYSA-N 0.000 description 2
RMQKWDVMKMTCGI-UHFFFAOYSA-N 1-methyl-3-[2-(pyridin-2-ylmethylsulfanyl)ethyl]thiourea Chemical compound CNC(=S)NCCSCC1=CC=CC=N1 RMQKWDVMKMTCGI-UHFFFAOYSA-N 0.000 description 2
241000700199 Cavia porcellus Species 0.000 description 2
239000000969 carrier Substances 0.000 description 2
229940079593 drug Drugs 0.000 description 2
239000003814 drug Substances 0.000 description 2
239000007903 gelatin capsule Substances 0.000 description 2
210000002837 heart atrium Anatomy 0.000 description 2
239000003112 inhibitor Substances 0.000 description 2
230000002401 inhibitory effect Effects 0.000 description 2
230000005764 inhibitory process Effects 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
YECBIJXISLIIDS-UHFFFAOYSA-N mepyramine Chemical compound C1=CC(OC)=CC=C1CN(CCN(C)C)C1=CC=CC=N1 YECBIJXISLIIDS-UHFFFAOYSA-N 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
102000005962 receptors Human genes 0.000 description 2
108020003175 receptors Proteins 0.000 description 2
239000006188 syrup Substances 0.000 description 2
235000020357 syrup Nutrition 0.000 description 2
KGVDAFVONJTQFZ-UHFFFAOYSA-N 1,3-bis[4-(1h-imidazol-5-yl)butyl]thiourea Chemical compound C=1NC=NC=1CCCCNC(=S)NCCCCC1=CNC=N1 KGVDAFVONJTQFZ-UHFFFAOYSA-N 0.000 description 1
GRBKDKADSNQICA-UHFFFAOYSA-N 1-[4-(4-bromo-1h-imidazol-5-yl)butyl]-3-methylthiourea Chemical compound CNC(=S)NCCCCC=1NC=NC=1Br GRBKDKADSNQICA-UHFFFAOYSA-N 0.000 description 1
BHXVXFKQYAHZKJ-UHFFFAOYSA-N 1-[5-(1h-imidazol-5-yl)pentyl]-3-methylthiourea Chemical compound CNC(=S)NCCCCCC1=CN=CN1 BHXVXFKQYAHZKJ-UHFFFAOYSA-N 0.000 description 1
OQZZEJLMVPNGFA-UHFFFAOYSA-N 1-methyl-3-[2-(1,3-thiazol-2-ylmethylsulfanyl)ethyl]thiourea Chemical compound CNC(=S)NCCSCC1=NC=CS1 OQZZEJLMVPNGFA-UHFFFAOYSA-N 0.000 description 1
WHSFCMKKZRMSEQ-UHFFFAOYSA-N 2-amino-2-iminoacetic acid Chemical class NC(=N)C(O)=O WHSFCMKKZRMSEQ-UHFFFAOYSA-N 0.000 description 1
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 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
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
241000282326 Felis catus Species 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
102000000543 Histamine Receptors Human genes 0.000 description 1
108010002059 Histamine Receptors Proteins 0.000 description 1
206010061218 Inflammation Diseases 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
240000007472 Leucaena leucocephala Species 0.000 description 1
235000010643 Leucaena leucocephala Nutrition 0.000 description 1
-1 N-methyl-N'-[2-(5-methyl-4-imidazolylthio)ethyl]-- thiourea Chemical compound 0.000 description 1
235000019483 Peanut oil Nutrition 0.000 description 1
108010079943 Pentagastrin Proteins 0.000 description 1
235000021355 Stearic acid Nutrition 0.000 description 1
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
229930006000 Sucrose Natural products 0.000 description 1
208000001871 Tachycardia Diseases 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000013543 active substance Substances 0.000 description 1
239000008272 agar Substances 0.000 description 1
235000010419 agar Nutrition 0.000 description 1
AOPRFYAPABFRPU-UHFFFAOYSA-N amino(imino)methanesulfonic acid Chemical class NC(=N)S(O)(=O)=O AOPRFYAPABFRPU-UHFFFAOYSA-N 0.000 description 1
239000003708 ampul Substances 0.000 description 1
239000005557 antagonist Substances 0.000 description 1
229940121363 anti-inflammatory agent Drugs 0.000 description 1
239000002260 anti-inflammatory agent Substances 0.000 description 1
239000000739 antihistaminic agent Substances 0.000 description 1
229940125715 antihistaminic agent Drugs 0.000 description 1
OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 1
239000002775 capsule Substances 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
210000000748 cardiovascular system Anatomy 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
SOYKEARSMXGVTM-UHFFFAOYSA-N chlorphenamine Chemical compound C=1C=CC=NC=1C(CCN(C)C)C1=CC=C(Cl)C=C1 SOYKEARSMXGVTM-UHFFFAOYSA-N 0.000 description 1
229960003291 chlorphenamine Drugs 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000006071 cream Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
125000004705 ethylthio group Chemical group C(C)S* 0.000 description 1
235000013305 food Nutrition 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
229940077716 histamine h2 receptor antagonists for peptic ulcer and gord Drugs 0.000 description 1
150000004677 hydrates Chemical class 0.000 description 1
230000004054 inflammatory process Effects 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
229940102223 injectable solution Drugs 0.000 description 1
230000003993 interaction Effects 0.000 description 1
239000003456 ion exchange resin Substances 0.000 description 1
229920003303 ion-exchange polymer Polymers 0.000 description 1
239000008101 lactose Substances 0.000 description 1
239000007937 lozenge Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
150000002689 maleic acids Chemical class 0.000 description 1
238000005259 measurement Methods 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
239000002674 ointment Substances 0.000 description 1
239000004006 olive oil Substances 0.000 description 1
235000008390 olive oil Nutrition 0.000 description 1
239000000312 peanut oil Substances 0.000 description 1
239000001814 pectin Substances 0.000 description 1
235000010987 pectin Nutrition 0.000 description 1
229920001277 pectin Polymers 0.000 description 1
239000008188 pellet Substances 0.000 description 1
ANRIQLNBZQLTFV-DZUOILHNSA-N pentagastrin Chemical compound C([C@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@@H](NC(=O)[C@H](CC=1[C]2C=CC=CC2=NC=1)NC(=O)CCNC(=O)OC(C)(C)C)CCSC)C(N)=O)C1=CC=CC=C1 ANRIQLNBZQLTFV-DZUOILHNSA-N 0.000 description 1
229960000444 pentagastrin Drugs 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
210000002784 stomach Anatomy 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
230000006794 tachycardia Effects 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
238000012360 testing method Methods 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
125000001425 triazolyl group Chemical group 0.000 description 1
210000004291 uterus Anatomy 0.000 description 1
229940124549 vasodilator Drugs 0.000 description 1
239000003071 vasodilator agent Substances 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1

Landscapes

Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CA320,456A 1976-03-11 1979-01-30 Preparation de derives des acides amidinosulfiniques Expired CA1075703A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA320,456A CA1075703A (fr)	1976-03-11	1979-01-30	Preparation de derives des acides amidinosulfiniques

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
GB9750/76A GB1574214A (en)	1976-03-11	1976-03-11	Amidines
CA273,246A CA1075700A (fr)	1976-03-11	1977-03-04	Preparation de derives des acides amidinoformiques
CA320,456A CA1075703A (fr)	1976-03-11	1979-01-30	Preparation de derives des acides amidinosulfiniques

Publications (1)

Publication Number	Publication Date
CA1075703A true CA1075703A (fr)	1980-04-15

Family

ID=27164949

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA320,456A Expired CA1075703A (fr)	1976-03-11	1979-01-30	Preparation de derives des acides amidinosulfiniques

Country Status (1)

Country	Link
CA (1)	CA1075703A (fr)

1979
- 1979-01-30 CA CA320,456A patent/CA1075703A/fr not_active Expired

Legal Events

Date	Code	Title	Description
1997-04-15	MKEX	Expiry

Publication	Publication Date	Title
CA1045142A (fr)	1978-12-26	Cyanoguanidines
CA1076579A (fr)	1980-04-29	Derives de la guanidine a action pharmacologique
CA1049524A (fr)	1979-02-27	Amidines substituees d'alcoyle heterocyclique
US4112104A (en)	1978-09-05	Pharmacologically active compounds
IE44124B1 (en)	1981-08-26	Cyclobutene-diones
CA1067501A (fr)	1979-12-04	Procede pour la preparation de guanidines substituees
CA1111040A (fr)	1981-10-20	Procede de fabrication de composes a base de sulfonylamidine
US4036971A (en)	1977-07-19	Amidino compounds
US4438127A (en)	1984-03-20	Pharmacologically active compounds
US4109003A (en)	1978-08-22	Pharmacologically active compounds
US3971786A (en)	1976-07-27	Pyridyl alkylguanidine compounds, composition therewith, and methods of inhibiting H-2 histamine receptors
CA1075703A (fr)	1980-04-15	Preparation de derives des acides amidinosulfiniques
US4084001A (en)	1978-04-11	Pharmacologically active compounds
US4120972A (en)	1978-10-17	Imidazolylmethylthio-ethyl isothiourea compounds
US4152453A (en)	1979-05-01	Pharmacologically active compounds and compositions and methods of use
US4173644A (en)	1979-11-06	Thiourea compounds, compositions and methods and use
US4120973A (en)	1978-10-17	Imidazolyl alkylaminocyclobutenediones
GB1565205A (en)	1980-04-16	Heterocyclic sulphoxides
US4166857A (en)	1979-09-04	N-Hetero substituted cyclobutenones
US4215125A (en)	1980-07-29	Pyridyl ureas, thioureas and guanidines
US4152443A (en)	1979-05-01	Imidazolyl thioureas, ureas and guanidines
CA1068713A (fr)	1979-12-25	Procede pour la preparation de guanidines substituees
US4191769A (en)	1980-03-04	Isothiourea compounds and pharmacological use
CA1068715A (fr)	1979-12-25	Procede pour la preparation de guanidines substituees
US4189488A (en)	1980-02-19	Amidinoformic and amidinosulphinic acids